Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

The cheapest airline(s) flying from Orlando to Chicago is Spirit Airlines.

  • Spirit Airlines Spirit Airlines
  • Frontier Airlines Frontier Airlines
  • American Airlines American Airlines
  • Delta Air Lines Delta Air Lines
  • United Airlines United Airlines
  • Sun Country Airlines Sun Country Airlines
  • Lufthansa Lufthansa
  • Air Canada Air Canada
  • British Airways British Airways
  • JetBlue Airways JetBlue Airways
Cheapest Month May

Travel Period: May 2024 - April 2025

The cheapest month(s) to fly from Orlando to Chicago is May.

  • May 2024
  • Jun 2024
  • Jul 2024
  • Aug 2024
  • Sep 2024
  • Oct 2024
  • Nov 2024
  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
Cheapest Day of the Week Thursday

The cheapest day(s) of the week to fly from Orlando to Chicago is Thursday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday
Cheapest Time 8pm

The cheapest time of the day to fly from Orlando to Chicago is in the evening.

Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm

Flight Schedules

Last Updated: Tue, 2 Apr, 2024

  • Depart Earliest
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  • Airline Filter by Airline
    All
  • Total Duration
    • Shortest
    • Longest
  • Stopover
    All
  • Availability
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 20:20 - 22:27
    MCO - ORD
  • 20:20 (MCO)Orlando International Airport
  • 22:27 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 2056)Airbus A320 Neo
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Airbus A320 Neo
  • 20:35 - 22:31
    MCO - MDW
  • 20:35 (MCO)Orlando International Airport
  • 22:31 (MDW)Chicago Midway Airport
  • Frontier Airlines (F9 4719)Airbus A320 Neo
  • 02h 56m
  • Direct
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Airbus A320 Neo
  • 20:40 - 22:36
    MCO - MDW
  • 20:40 (MCO)Orlando International Airport
  • 22:36 (MDW)Chicago Midway Airport
  • Frontier Airlines (F9 4719)Airbus A320 Neo
  • 02h 56m
  • Direct
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Airbus A320 Neo
  • 20:40 - 22:25
    MCO - MDW
  • 20:40 (MCO)Orlando International Airport
  • 22:25 (MDW)Chicago Midway Airport
  • (WN 1328)Boeing 737 700
  • 02h 45m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 20:45 - 22:52
    MCO - ORD
  • 20:45 (MCO)Orlando International Airport
  • 22:52 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1536)Boeing 737 900
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Boeing 737 900
  • 21:20 - 23:26
    MCO - ORD
  • 21:20 (MCO)Orlando International Airport
  • 23:26 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 2056)Airbus A320 Neo
  • 03h 06m
  • Direct
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Airbus A320 Neo
  • 21:20 - 23:10
    MCO - MDW
  • 21:20 (MCO)Orlando International Airport
  • 23:10 (MDW)Chicago Midway Airport
  • (WN 1328)Boeing 737 800
  • 02h 50m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 21:30 - 23:20
    MCO - MDW
  • 21:30 (MCO)Orlando International Airport
  • 23:20 (MDW)Chicago Midway Airport
  • (WN 1328)Boeing 737 Max 8 Passenger
  • 02h 50m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 Max 8 Passenger
  • 21:39 - 23:43
    MCO - ORD
  • 21:39 (MCO)Orlando International Airport
  • 23:43 (ORD)Chicago O'Hare International Airport
  • Frontier Airlines (F9 3043)Airbus
  • 03h 04m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Airbus
  • 21:45 - 23:30
    MCO - MDW
  • 21:45 (MCO)Orlando International Airport
  • 23:30 (MDW)Chicago Midway Airport
  • (WN 1328)Boeing 737 Max 8 Passenger
  • 02h 45m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 22:07 - 00:09+ 1
    MCO - ORD
  • 22:07 (MCO)Orlando International Airport
  • 00:09 (ORD)Chicago O'Hare International Airport + 1
  • Spirit Airlines (NK 2056)Airbus Industrie A320 Sharklets
  • 03h 02m
  • Direct
    • -
    • -
    • W
    • -
    • -
    • -
    • -
  • Airbus Industrie A320 Sharklets
  • 22:52 - 00:59+ 1
    MCO - ORD
  • 22:52 (MCO)Orlando International Airport
  • 00:59 (ORD)Chicago O'Hare International Airport + 1
  • Frontier Airlines (F9 2791)Airbus
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus
  • 23:20 - 01:26+ 1
    MCO - ORD
  • 23:20 (MCO)Orlando International Airport
  • 01:26 (ORD)Chicago O'Hare International Airport + 1
  • Spirit Airlines (NK 2056)Airbus A320 Neo
  • 03h 06m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus A320 Neo
  • 06:30 - 08:13
    SFB - RFD
  • 06:30 (SFB)Orlando Sanford International Airport
  • 08:13 (RFD)Chicago Rockford Airport
  • Allegiant Air LLC (G4 2861)Airbus
  • 02h 43m
  • Direct
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Airbus
  • 06:30 - 08:15
    MCO - MDW
  • 06:30 (MCO)Orlando International Airport
  • 08:15 (MDW)Chicago Midway Airport
  • (WN 6125)Boeing 737 800
  • 02h 45m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 06:55 - 09:55
    MCO - MDW
  • 06:55 (MCO)Orlando International Airport
  • 09:55 (MDW)Chicago Midway Airport
  • (WN 5590)Boeing 737 700
  • 04h 00m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 07:00 - 09:10
    MCO - ORD
  • 07:00 (MCO)Orlando International Airport
  • 09:10 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 557)Boeing 737 Max 8 Passenger
  • 03h 10m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Boeing 737 Max 8 Passenger
  • 07:15 - 09:25
    MCO - ORD
  • 07:15 (MCO)Orlando International Airport
  • 09:25 (ORD)Chicago O'Hare International Airport
  • (WN 3648)Boeing 737 700
  • 03h 10m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 07:15 - 09:05
    MCO - MDW
  • 07:15 (MCO)Orlando International Airport
  • 09:05 (MDW)Chicago Midway Airport
  • (WN 5117)Boeing 737 700
  • 02h 50m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 07:30 - 09:34
    MCO - ORD
  • 07:30 (MCO)Orlando International Airport
  • 09:34 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1843)Boeing 737 900
  • 03h 04m
  • Direct
    • -
    • -
    • -
    • T
    • F
    • S
    • S
  • Boeing 737 900
  • 07:30 - 09:34
    MCO - ORD
  • 07:30 (MCO)Orlando International Airport
  • 09:34 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1957)Boeing 737 900
  • 03h 04m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • -
    • -
  • Boeing 737 900
  • 07:35 - 09:20
    MCO - MDW
  • 07:35 (MCO)Orlando International Airport
  • 09:20 (MDW)Chicago Midway Airport
  • (WN 5117)Boeing 737 700
  • 02h 45m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 07:45 - 09:35
    MCO - MDW
  • 07:45 (MCO)Orlando International Airport
  • 09:35 (MDW)Chicago Midway Airport
  • (WN 5117)Boeing 737 800
  • 02h 50m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 07:55 - 09:45
    MCO - MDW
  • 07:55 (MCO)Orlando International Airport
  • 09:45 (MDW)Chicago Midway Airport
  • (WN 5117)Boeing 737 700
  • 02h 50m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 700
  • 09:05 - 10:50
    MCO - MDW
  • 09:05 (MCO)Orlando International Airport
  • 10:50 (MDW)Chicago Midway Airport
  • (WN 3156)Boeing 737 700
  • 02h 45m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 09:30 - 11:30
    MCO - ORD
  • 09:30 (MCO)Orlando International Airport
  • 11:30 (ORD)Chicago O'Hare International Airport
  • (WN 934)Boeing 737 800
  • 03h 00m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 09:40 - 11:25
    MCO - MDW
  • 09:40 (MCO)Orlando International Airport
  • 11:25 (MDW)Chicago Midway Airport
  • (WN 3156)Boeing 737 Max 8 Passenger
  • 02h 45m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 09:45 - 11:30
    MCO - MDW
  • 09:45 (MCO)Orlando International Airport
  • 11:30 (MDW)Chicago Midway Airport
  • (WN 3156)Boeing 737 800
  • 02h 45m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 09:50 - 11:35
    MCO - MDW
  • 09:50 (MCO)Orlando International Airport
  • 11:35 (MDW)Chicago Midway Airport
  • (WN 3156)Boeing 737 800
  • 02h 45m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 09:55 - 11:52
    MCO - MDW
  • 09:55 (MCO)Orlando International Airport
  • 11:52 (MDW)Chicago Midway Airport
  • Frontier Airlines (F9 1457)Airbus A320 Neo
  • 02h 57m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus A320 Neo
  • 09:55 - 12:03
    MCO - ORD
  • 09:55 (MCO)Orlando International Airport
  • 12:03 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1941)Airbus A321 Neo
  • 03h 08m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Airbus A321 Neo
  • 10:10 - 12:00
    MCO - MDW
  • 10:10 (MCO)Orlando International Airport
  • 12:00 (MDW)Chicago Midway Airport
  • (WN 4855)Boeing 737 800
  • 02h 50m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 10:29 - 12:31
    MCO - ORD
  • 10:29 (MCO)Orlando International Airport
  • 12:31 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 2870)Boeing 737 800
  • 03h 02m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Boeing 737 800
  • 10:40 - 13:55
    MCO - MDW
  • 10:40 (MCO)Orlando International Airport
  • 13:55 (MDW)Chicago Midway Airport
  • (WN 2557)Boeing 737 700
  • 04h 15m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 10:50 - 12:57
    MCO - ORD
  • 10:50 (MCO)Orlando International Airport
  • 12:57 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2421)Boeing 737 800
  • 03h 07m
  • Direct
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 10:50 - 12:57
    MCO - ORD
  • 10:50 (MCO)Orlando International Airport
  • 12:57 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2421)Boeing 737 900
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 900
  • 11:00 - 14:20
    MCO - MDW
  • 11:00 (MCO)Orlando International Airport
  • 14:20 (MDW)Chicago Midway Airport
  • (WN 3207)Boeing 737 700
  • 04h 20m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 11:00 - 13:00
    MCO - ORD
  • 11:00 (MCO)Orlando International Airport
  • 13:00 (ORD)Chicago O'Hare International Airport
  • (WN 934)Boeing 737 800
  • 03h 00m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 11:05 - 14:05
    MCO - MDW
  • 11:05 (MCO)Orlando International Airport
  • 14:05 (MDW)Chicago Midway Airport
  • (WN 6025)Boeing 737 700
  • 04h 00m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 11:15 - 13:00
    MCO - MDW
  • 11:15 (MCO)Orlando International Airport
  • 13:00 (MDW)Chicago Midway Airport
  • (WN 6125)Boeing 737 Max 8 Passenger
  • 02h 45m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 11:55 - 14:00
    MCO - ORD
  • 11:55 (MCO)Orlando International Airport
  • 14:00 (ORD)Chicago O'Hare International Airport
  • (WN 3648)Boeing 737 800
  • 03h 05m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 12:20 - 14:25
    MCO - ORD
  • 12:20 (MCO)Orlando International Airport
  • 14:25 (ORD)Chicago O'Hare International Airport
  • (WN 934)Boeing 737 800
  • 03h 05m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 12:39 - 14:45
    MCO - ORD
  • 12:39 (MCO)Orlando International Airport
  • 14:45 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2475)Boeing 757 300 Series
  • 03h 06m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Boeing 757 300 Series
  • 12:40 - 14:25
    MCO - MDW
  • 12:40 (MCO)Orlando International Airport
  • 14:25 (MDW)Chicago Midway Airport
  • (WN 3157)Boeing 737 Max 8 Passenger
  • 02h 45m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 Max 8 Passenger
  • 12:45 - 15:45
    MCO - MDW
  • 12:45 (MCO)Orlando International Airport
  • 15:45 (MDW)Chicago Midway Airport
  • (WN 1219)Boeing 737 700
  • 04h 00m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 12:49 - 14:55
    MCO - ORD
  • 12:49 (MCO)Orlando International Airport
  • 14:55 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2475)Boeing 757 300 Series
  • 03h 06m
  • Direct
    • -
    • -
    • -
    • T
    • F
    • S
    • S
  • Boeing 757 300 Series
  • 12:50 - 14:35
    MCO - MDW
  • 12:50 (MCO)Orlando International Airport
  • 14:35 (MDW)Chicago Midway Airport
  • (WN 3157)Boeing 737 800
  • 02h 45m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 13:05 - 16:25
    MCO - MDW
  • 13:05 (MCO)Orlando International Airport
  • 16:25 (MDW)Chicago Midway Airport
  • (WN 3207)Boeing 737 700
  • 04h 20m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 13:05 - 14:50
    MCO - MDW
  • 13:05 (MCO)Orlando International Airport
  • 14:50 (MDW)Chicago Midway Airport
  • (WN 3157)Boeing 737 Max 8 Passenger
  • 02h 45m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 13:25 - 15:15
    MCO - MDW
  • 13:25 (MCO)Orlando International Airport
  • 15:15 (MDW)Chicago Midway Airport
  • (WN 3157)Boeing 737 800
  • 02h 50m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 13:55 - 15:53
    MCO - ORD
  • 13:55 (MCO)Orlando International Airport
  • 15:53 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 2119)Airbus
  • 02h 58m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus
  • 14:00 - 16:03
    MCO - ORD
  • 14:00 (MCO)Orlando International Airport
  • 16:03 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 2119)Boeing 737 800
  • 03h 03m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 14:30 - 17:35
    MCO - MDW
  • 14:30 (MCO)Orlando International Airport
  • 17:35 (MDW)Chicago Midway Airport
  • (WN 5489)Boeing 737 700
  • 04h 05m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 14:40 - 16:45
    MCO - ORD
  • 14:40 (MCO)Orlando International Airport
  • 16:45 (ORD)Chicago O'Hare International Airport
  • (WN 3650)Boeing 737 700
  • 03h 05m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 14:40 - 16:45
    MCO - ORD
  • 14:40 (MCO)Orlando International Airport
  • 16:45 (ORD)Chicago O'Hare International Airport
  • (WN 3650)Boeing 737 Max 8 Passenger
  • 03h 05m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 14:45 - 16:30
    MCO - MDW
  • 14:45 (MCO)Orlando International Airport
  • 16:30 (MDW)Chicago Midway Airport
  • (WN 3313)Boeing 737 700
  • 02h 45m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 14:55 - 18:30
    MCO - MDW
  • 14:55 (MCO)Orlando International Airport
  • 18:30 (MDW)Chicago Midway Airport
  • (WN 2282)Boeing 737 700
  • 04h 35m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 15:09 - 17:05
    MCO - MDW
  • 15:09 (MCO)Orlando International Airport
  • 17:05 (MDW)Chicago Midway Airport
  • Frontier Airlines (F9 3853)Airbus A320 Neo
  • 02h 56m
  • Direct
    • -
    • -
    • -
    • T
    • -
    • -
    • -
  • Airbus A320 Neo
  • 15:25 - 18:20
    MCO - MDW
  • 15:25 (MCO)Orlando International Airport
  • 18:20 (MDW)Chicago Midway Airport
  • (WN 2686)Boeing 737 700
  • 03h 55m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 15:35 - 17:25
    MCO - MDW
  • 15:35 (MCO)Orlando International Airport
  • 17:25 (MDW)Chicago Midway Airport
  • (WN 3313)Boeing 737 800
  • 02h 50m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 15:44 - 17:40
    MCO - MDW
  • 15:44 (MCO)Orlando International Airport
  • 17:40 (MDW)Chicago Midway Airport
  • Frontier Airlines (F9 3853)Airbus A320 Neo
  • 02h 56m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus A320 Neo
  • 15:50 - 17:40
    MCO - MDW
  • 15:50 (MCO)Orlando International Airport
  • 17:40 (MDW)Chicago Midway Airport
  • (WN 3313)Boeing 737 800
  • 02h 50m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 16:11 - 18:18
    MCO - ORD
  • 16:11 (MCO)Orlando International Airport
  • 18:18 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 2056)Airbus Industrie A320 Sharklets
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Airbus Industrie A320 Sharklets
  • 16:15 - 18:22
    MCO - ORD
  • 16:15 (MCO)Orlando International Airport
  • 18:22 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1828)Boeing 737 Max 9 Passenger
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 Max 9 Passenger
  • 16:15 - 18:22
    MCO - ORD
  • 16:15 (MCO)Orlando International Airport
  • 18:22 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1828)Boeing 737 900
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 900
  • 16:29 - 18:18
    SFB - RFD
  • 16:29 (SFB)Orlando Sanford International Airport
  • 18:18 (RFD)Chicago Rockford Airport
  • Allegiant Air LLC (G4 2815)Airbus
  • 02h 49m
  • Direct
    • M
    • -
    • -
    • -
    • F
    • -
    • -
  • Airbus
  • 16:55 - 21:25
    MCO - MDW
  • 16:55 (MCO)Orlando International Airport
  • 21:25 (MDW)Chicago Midway Airport
  • (WN 3194)Boeing 737 800
  • 05h 30m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 17:00 - 18:55
    MCO - MDW
  • 17:00 (MCO)Orlando International Airport
  • 18:55 (MDW)Chicago Midway Airport
  • (WN 998)Boeing 737 800
  • 02h 55m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 17:15 - 20:15
    MCO - MDW
  • 17:15 (MCO)Orlando International Airport
  • 20:15 (MDW)Chicago Midway Airport
  • (WN 3768)Boeing 737 700
  • 04h 00m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 17:30 - 19:27
    MCO - MDW
  • 17:30 (MCO)Orlando International Airport
  • 19:27 (MDW)Chicago Midway Airport
  • Frontier Airlines (F9 3853)Airbus A320 Neo
  • 02h 57m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Airbus A320 Neo
  • 17:37 - 19:36
    MCO - ORD
  • 17:37 (MCO)Orlando International Airport
  • 19:36 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 1782)Airbus
  • 02h 59m
  • Direct
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • Airbus
  • 17:37 - 19:40
    MCO - ORD
  • 17:37 (MCO)Orlando International Airport
  • 19:40 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 1782)Boeing 737 800
  • 03h 03m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Boeing 737 800
  • 18:00 - 19:50
    MCO - MDW
  • 18:00 (MCO)Orlando International Airport
  • 19:50 (MDW)Chicago Midway Airport
  • (WN 3158)Boeing 737 Max 8 Passenger
  • 02h 50m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 18:15 - 20:10
    MCO - MDW
  • 18:15 (MCO)Orlando International Airport
  • 20:10 (MDW)Chicago Midway Airport
  • (WN 3158)Boeing 737 800
  • 02h 55m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 18:15 - 20:22
    MCO - ORD
  • 18:15 (MCO)Orlando International Airport
  • 20:22 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1871)Boeing 737 900
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Boeing 737 900
  • 18:18 - 20:25
    MCO - ORD
  • 18:18 (MCO)Orlando International Airport
  • 20:25 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1871)Boeing 737 900
  • 03h 07m
  • Direct
    • -
    • -
    • -
    • T
    • F
    • S
    • S
  • Boeing 737 900
  • 18:20 - 22:10
    MCO - MDW
  • 18:20 (MCO)Orlando International Airport
  • 22:10 (MDW)Chicago Midway Airport
  • (WN 2302)Boeing 737 700
  • 04h 50m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 700
  • 18:27 - 20:35
    MCO - ORD
  • 18:27 (MCO)Orlando International Airport
  • 20:35 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 793)Airbus A320 Neo
  • 03h 08m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Airbus A320 Neo
  • 18:30 - 20:20
    MCO - MDW
  • 18:30 (MCO)Orlando International Airport
  • 20:20 (MDW)Chicago Midway Airport
  • (WN 3158)Boeing 737 700
  • 02h 50m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 18:50 - 20:55
    MCO - ORD
  • 18:50 (MCO)Orlando International Airport
  • 20:55 (ORD)Chicago O'Hare International Airport
  • (WN 3650)Boeing 737 Max 8 Passenger
  • 03h 05m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 Max 8 Passenger
  • 18:55 - 20:50
    MCO - MDW
  • 18:55 (MCO)Orlando International Airport
  • 20:50 (MDW)Chicago Midway Airport
  • (WN 3159)Boeing 737 700
  • 02h 55m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 19:10 - 21:00
    MCO - MDW
  • 19:10 (MCO)Orlando International Airport
  • 21:00 (MDW)Chicago Midway Airport
  • (WN 3159)Boeing 737 800
  • 02h 50m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 19:50 - 21:57
    MCO - ORD
  • 19:50 (MCO)Orlando International Airport
  • 21:57 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 2056)Airbus A320 Neo
  • 03h 07m
  • Direct
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • Airbus A320 Neo

Connecting Flights

  • 20:15 - 21:20+ 1
    MCO - BNA
    22:40 - 00:10+ 1
    BNA - MDW
  • 20:15 (MCO)Orlando International Airport
    22:40 (BNA)Nashville Airport
  • 21:20 (BNA)Nashville Airport + 1
    00:10 (MDW)Chicago Midway Airport
  • (WN 6706)Boeing 737 700
    (WN 5212)Boeing 737 700
  • 04h 55m (01h 20m)
  • BNA Nashville 01h 20m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 20:15 - 21:55
    MCO - STL
    22:50 - 23:55
    STL - MDW
  • 20:15 (MCO)Orlando International Airport
    22:50 (STL)St Louis Lambert Intl Airport
  • 21:55 (STL)St Louis Lambert Intl Airport
    23:55 (MDW)Chicago Midway Airport
  • (WN 4942)Boeing 737 800
    (WN 3244)Boeing 737 800
  • 04h 40m (00h 55m)
  • STL Saint Louis 00h 55m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 05:00 - 06:43
    MCO - CLT
    07:49 - 08:55
    CLT - ORD
  • 05:00 (MCO)Orlando International Airport
    07:49 (CLT)Charlotte Airport
  • 06:43 (CLT)Charlotte Airport
    08:55 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 1896)Airbus
    American Airlines (AA 459)Airbus
  • 04h 55m (01h 06m)
  • CLT Charlotte 01h 06m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 05:00 - 06:43
    MCO - CLT
    09:08 - 10:15
    CLT - ORD
  • 05:00 (MCO)Orlando International Airport
    09:08 (CLT)Charlotte Airport
  • 06:43 (CLT)Charlotte Airport
    10:15 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 1896)Airbus
    American Airlines (AA 1038)Airbus
  • 06h 15m (02h 25m)
  • CLT Charlotte 02h 25m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 05:10 - 06:54
    MCO - CLT
    09:21 - 10:32
    CLT - ORD
  • 05:10 (MCO)Orlando International Airport
    09:21 (CLT)Charlotte Airport
  • 06:54 (CLT)Charlotte Airport
    10:32 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 1148)Airbus Industrie A320 Sharklets
    Spirit Airlines (NK 1175)Airbus Industrie A321 Sharklets
  • 06h 22m (02h 27m)
  • CLT Charlotte 02h 27m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 05:30 - 07:02
    MCO - ATL
    08:10 - 09:05
    ATL - MDW
  • 05:30 (MCO)Orlando International Airport
    08:10 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 07:02 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    09:05 (MDW)Chicago Midway Airport
  • Delta Air Lines (DL 2525)Boeing 757
    Delta Air Lines (DL 1063)Boeing 717
  • 04h 35m (01h 08m)
  • ATL Atlanta 01h 08m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 05:30 - 07:03
    MCO - ATL
    08:15 - 09:10
    ATL - MDW
  • 05:30 (MCO)Orlando International Airport
    08:15 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 07:03 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    09:10 (MDW)Chicago Midway Airport
  • Delta Air Lines (DL 2525)Boeing 757
    Delta Air Lines (DL 1063)Boeing 717
  • 04h 40m (01h 12m)
  • ATL Atlanta 01h 12m
    • -
    • -
    • -
    • T
    • F
    • -
    • S
  • 05:30 - 07:03
    MCO - ATL
    09:15 - 10:10
    ATL - MDW
  • 05:30 (MCO)Orlando International Airport
    09:15 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 07:03 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    10:10 (MDW)Chicago Midway Airport
  • Delta Air Lines (DL 2525)Boeing 757
    Delta Air Lines (DL 2417)Boeing 717
  • 05h 40m (02h 12m)
  • ATL Atlanta 02h 12m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:00 - 08:43
    MCO - EWR
    10:00 - 11:40
    EWR - ORD
  • 06:00 (MCO)Orlando International Airport
    10:00 (EWR)Newark Liberty International Airport
  • 08:43 (EWR)Newark Liberty International Airport
    11:40 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2607)Boeing 737 900
    United Airlines (UA 1237)Boeing 737 Max 8 Passenger
  • 06h 40m (01h 17m)
  • EWR New York City 01h 17m
    • -
    • -
    • -
    • T
    • -
    • -
    • -
  • 06:00 - 08:43
    MCO - EWR
    10:00 - 11:40
    EWR - ORD
  • 06:00 (MCO)Orlando International Airport
    10:00 (EWR)Newark Liberty International Airport
  • 08:43 (EWR)Newark Liberty International Airport
    11:40 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2607)Boeing 737 Max 9 Passenger
    United Airlines (UA 1237)Boeing 737 900
  • 06h 40m (01h 17m)
  • EWR New York City 01h 17m
    • -
    • -
    • -
    • -
    • F
    • S
    • S
  • 06:05 - 08:05
    MCO - MCI
    10:20 - 11:45
    MCI - MDW
  • 06:05 (MCO)Orlando International Airport
    10:20 (MCI)Kansas City International Airport
  • 08:05 (MCI)Kansas City International Airport
    11:45 (MDW)Chicago Midway Airport
  • (WN 853)Boeing 737 800
    (WN 4988)Boeing 737 700
  • 06h 40m (02h 15m)
  • MCI Kansas City 02h 15m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:10 - 07:45
    MCO - ATL
    09:50 - 10:45
    ATL - MDW
  • 06:10 (MCO)Orlando International Airport
    09:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 07:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    10:45 (MDW)Chicago Midway Airport
  • (WN 263)Boeing 737 800
    (WN 5518)Boeing 737 700
  • 05h 35m (02h 05m)
  • ATL Atlanta 02h 05m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 06:13 - 08:01
    MCO - CLT
    09:08 - 10:15
    CLT - ORD
  • 06:13 (MCO)Orlando International Airport
    09:08 (CLT)Charlotte Airport
  • 08:01 (CLT)Charlotte Airport
    10:15 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 1647)Airbus
    American Airlines (AA 1038)Airbus
  • 05h 02m (01h 07m)
  • CLT Charlotte 01h 07m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 06:15 - 07:50
    MCO - ATL
    10:40 - 11:35
    ATL - MDW
  • 06:15 (MCO)Orlando International Airport
    10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 07:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    11:35 (MDW)Chicago Midway Airport
  • (WN 263)Boeing 737 Max 8 Passenger
    (WN 5518)Boeing 737 Max 8 Passenger
  • 06h 20m (02h 50m)
  • ATL Atlanta 02h 50m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:20 - 08:10
    MCO - DAL
    09:10 - 11:30
    DAL - ORD
  • 06:20 (MCO)Orlando International Airport
    09:10 (DAL)Dallas/Fort Worth Love Field Airport
  • 08:10 (DAL)Dallas/Fort Worth Love Field Airport
    11:30 (ORD)Chicago O'Hare International Airport
  • (WN 1389)Boeing 737 700
    (WN 4903)Boeing 737 800
  • 06h 10m (01h 00m)
  • DAL Dallas 01h 00m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 06:20 - 08:10
    MCO - AUS
    09:05 - 11:35
    AUS - MDW
  • 06:20 (MCO)Orlando International Airport
    09:05 (AUS)Austin-Bergstrom International Airport
  • 08:10 (AUS)Austin-Bergstrom International Airport
    11:35 (MDW)Chicago Midway Airport
  • (WN 6146)Boeing 737 700
    (WN 3033)Boeing 737 700
  • 06h 15m (00h 55m)
  • AUS Austin 00h 55m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 06:22 - 07:35
    MCO - MIA
    08:34 - 11:04
    MIA - ORD
  • 06:22 (MCO)Orlando International Airport
    08:34 (MIA)Miami International Airport
  • 07:35 (MIA)Miami International Airport
    11:04 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 2894)Boeing 737 Max 8 Passenger
    American Airlines (AA 1949)Boeing 737 800
  • 05h 42m (00h 59m)
  • MIA Miami 00h 59m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 06:25 - 09:16
    MCO - YYZ
    11:00 - 12:04
    YYZ - ORD
  • 06:25 (MCO)Orlando International Airport
    11:00 (YYZ)Toronto Lester B Pearson Intl Airport
  • 09:16 (YYZ)Toronto Lester B Pearson Intl Airport
    12:04 (ORD)Chicago O'Hare International Airport
  • Air Canada (AC 1671)Airbus
    United Airlines (UA 5454)Embraer 175
  • 06h 39m (01h 44m)
  • YYZ Toronto 01h 44m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 06:30 - 08:05
    MCO - ATL
    09:55 - 10:50
    ATL - MDW
  • 06:30 (MCO)Orlando International Airport
    09:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 08:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    10:50 (MDW)Chicago Midway Airport
  • (WN 263)Boeing 737 700
    (WN 5518)Boeing 737 700
  • 05h 20m (01h 50m)
  • ATL Atlanta 01h 50m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:30 - 08:07
    MCO - ATL
    09:15 - 10:10
    ATL - MDW
  • 06:30 (MCO)Orlando International Airport
    09:15 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 08:07 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    10:10 (MDW)Chicago Midway Airport
  • Delta Air Lines (DL 846)Boeing 757
    Delta Air Lines (DL 2417)Boeing 717
  • 04h 40m (01h 08m)
  • ATL Atlanta 01h 08m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:35 - 08:10
    MCO - ATL
    10:45 - 11:40
    ATL - MDW
  • 06:35 (MCO)Orlando International Airport
    10:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 08:10 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    11:40 (MDW)Chicago Midway Airport
  • (WN 263)Boeing 737 800
    (WN 5518)Boeing 737 Max 8 Passenger
  • 06h 05m (02h 35m)
  • ATL Atlanta 02h 35m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 06:35 - 08:50
    MCO - DCA
    09:40 - 10:45
    DCA - MDW
  • 06:35 (MCO)Orlando International Airport
    09:40 (DCA)Washington Ronald Reagan National Airport
  • 08:50 (DCA)Washington Ronald Reagan National Airport
    10:45 (MDW)Chicago Midway Airport
  • (WN 1499)Boeing 737 700
    (WN 3086)Boeing 737 700
  • 05h 10m (00h 50m)
  • DCA Washington 00h 50m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:45 - 07:45
    MCO - BNA
    09:00 - 10:45
    BNA - ORD
  • 06:45 (MCO)Orlando International Airport
    09:00 (BNA)Nashville Airport
  • 07:45 (BNA)Nashville Airport
    10:45 (ORD)Chicago O'Hare International Airport
  • (WN 3287)Boeing 737 700
    (WN 510)Boeing 737 700
  • 05h 00m (01h 15m)
  • BNA Nashville 01h 15m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:45 - 07:45
    MCO - BNA
    09:45 - 11:15
    BNA - MDW
  • 06:45 (MCO)Orlando International Airport
    09:45 (BNA)Nashville Airport
  • 07:45 (BNA)Nashville Airport
    11:15 (MDW)Chicago Midway Airport
  • (WN 3287)Boeing 737 700
    (WN 2119)Boeing 737 700
  • 05h 30m (02h 00m)
  • BNA Nashville 02h 00m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:55 - 08:41
    MCO - CLT
    09:21 - 10:32
    CLT - ORD
  • 06:55 (MCO)Orlando International Airport
    09:21 (CLT)Charlotte Airport
  • 08:41 (CLT)Charlotte Airport
    10:32 (ORD)Chicago O'Hare International Airport
  • Spirit Airlines (NK 1148)Airbus Industrie A320 Sharklets
    Spirit Airlines (NK 1175)Airbus Industrie A321 Sharklets
  • 04h 37m (00h 40m)
  • CLT Charlotte 00h 40m
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • 07:00 - 08:42
    MCO - ATL
    10:20 - 11:23
    ATL - ORD
  • 07:00 (MCO)Orlando International Airport
    10:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 08:42 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    11:23 (ORD)Chicago O'Hare International Airport
  • Delta Air Lines (DL 640)Boeing 757
    Delta Air Lines (DL 1147)Boeing 757 200 Series
  • 05h 23m (01h 38m)
  • ATL Atlanta 01h 38m
    • -
    • -
    • -
    • T
    • F
    • S
    • S
  • 07:00 - 09:20
    MCO - CMH
    10:50 - 11:05
    CMH - MDW
  • 07:00 (MCO)Orlando International Airport
    10:50 (CMH)Columbus Port Columbus Intl Airport
  • 09:20 (CMH)Columbus Port Columbus Intl Airport
    11:05 (MDW)Chicago Midway Airport
  • (WN 1218)Boeing 737 700
    (WN 5203)Boeing 737 700
  • 05h 05m (01h 30m)
  • CMH Columbus 01h 30m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:00 - 09:30
    MCO - MSP
    10:00 - 11:25
    MSP - ORD
  • 07:00 (MCO)Orlando International Airport
    10:00 (MSP)Minneapolis International Airport
  • 09:30 (MSP)Minneapolis International Airport
    11:25 (ORD)Chicago O'Hare International Airport
  • Delta Air Lines (DL 1208)Boeing 757 300 Series
    Delta Air Lines (DL 1367)Boeing 717
  • 05h 25m (00h 30m)
  • MSP Minneapolis 00h 30m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:00 - 08:43
    MCO - IAH
    10:05 - 12:51
    IAH - ORD
  • 07:00 (MCO)Orlando International Airport
    10:05 (IAH)Houston George Bush Intercontinental Airport
  • 08:43 (IAH)Houston George Bush Intercontinental Airport
    12:51 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2233)Boeing 737 900
    United Airlines (UA 2282)Airbus A321 Neo
  • 06h 51m (01h 22m)
  • IAH Houston 01h 22m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:00 - 09:03
    MCO - DFW
    10:09 - 12:35
    DFW - ORD
  • 07:00 (MCO)Orlando International Airport
    10:09 (DFW)Dallas/Fort Worth Intl Airport
  • 09:03 (DFW)Dallas/Fort Worth Intl Airport
    12:35 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 668)Airbus
    American Airlines (AA 1805)Boeing 737 800
  • 06h 35m (01h 06m)
  • DFW Dallas 01h 06m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 07:00 - 08:41
    MCO - ATL
    10:20 - 11:22
    ATL - ORD
  • 07:00 (MCO)Orlando International Airport
    10:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • 08:41 (ATL)Atlanta Hartsfield-Jackson Intl Airport
    11:22 (ORD)Chicago O'Hare International Airport
  • Delta Air Lines (DL 640)Boeing 757
    Delta Air Lines (DL 1147)Boeing 757 200 Series
  • 05h 22m (01h 39m)
  • ATL Atlanta 01h 39m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 07:00 - 08:43
    MCO - IAH
    10:05 - 12:51
    IAH - ORD
  • 07:00 (MCO)Orlando International Airport
    10:05 (IAH)Houston George Bush Intercontinental Airport
  • 08:43 (IAH)Houston George Bush Intercontinental Airport
    12:51 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2233)Boeing 737 800
    United Airlines (UA 2282)Airbus A321 Neo
  • 06h 51m (01h 22m)
  • IAH Houston 01h 22m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:01 - 09:25
    MCO - DCA
    09:56 - 11:09
    DCA - ORD
  • 07:01 (MCO)Orlando International Airport
    09:56 (DCA)Washington Ronald Reagan National Airport
  • 09:25 (DCA)Washington Ronald Reagan National Airport
    11:09 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 511)Boeing 737 800
    American Airlines (AA 978)Airbus
  • 05h 08m (00h 31m)
  • DCA Washington 00h 31m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:04 - 09:52
    MCO - EWR
    10:59 - 12:39
    EWR - ORD
  • 07:04 (MCO)Orlando International Airport
    10:59 (EWR)Newark Liberty International Airport
  • 09:52 (EWR)Newark Liberty International Airport
    12:39 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1067)Boeing 737 900
    United Airlines (UA 1027)Airbus
  • 06h 35m (01h 07m)
  • EWR New York City 01h 07m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:04 - 09:52
    MCO - EWR
    10:59 - 12:39
    EWR - ORD
  • 07:04 (MCO)Orlando International Airport
    10:59 (EWR)Newark Liberty International Airport
  • 09:52 (EWR)Newark Liberty International Airport
    12:39 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1067)Boeing 737 900
    United Airlines (UA 1027)Boeing 737 Max 9 Passenger
  • 06h 35m (01h 07m)
  • EWR New York City 01h 07m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:04 - 09:52
    MCO - EWR
    10:59 - 12:39
    EWR - ORD
  • 07:04 (MCO)Orlando International Airport
    10:59 (EWR)Newark Liberty International Airport
  • 09:52 (EWR)Newark Liberty International Airport
    12:39 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1067)Boeing 737 900
    United Airlines (UA 1027)Boeing 737 900
  • 06h 35m (01h 07m)
  • EWR New York City 01h 07m
    • -
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:04 - 09:52
    MCO - EWR
    10:59 - 12:39
    EWR - ORD
  • 07:04 (MCO)Orlando International Airport
    10:59 (EWR)Newark Liberty International Airport
  • 09:52 (EWR)Newark Liberty International Airport
    12:39 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 2003)Boeing 737 900
    United Airlines (UA 1027)Boeing 737 900
  • 06h 35m (01h 07m)
  • EWR New York City 01h 07m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:05 - 09:40
    MCO - PHL
    11:00 - 12:29
    PHL - ORD
  • 07:05 (MCO)Orlando International Airport
    11:00 (PHL)Philadelphia International Airport
  • 09:40 (PHL)Philadelphia International Airport
    12:29 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 632)Airbus
    American Airlines (AA 1959)Airbus
  • 06h 24m (01h 20m)
  • PHL Philadelphia 01h 20m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • 07:05 - 09:30
    MCO - PIT
    11:25 - 11:50
    PIT - MDW
  • 07:05 (MCO)Orlando International Airport
    11:25 (PIT)Pittsburgh International Airport
  • 09:30 (PIT)Pittsburgh International Airport
    11:50 (MDW)Chicago Midway Airport
  • (WN 3930)Boeing 737 700
    (WN 472)Boeing 737 700
  • 05h 45m (01h 55m)
  • PIT Pittsburgh 01h 55m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:05 - 09:20
    MCO - CMH
    11:10 - 11:25
    CMH - MDW
  • 07:05 (MCO)Orlando International Airport
    11:10 (CMH)Columbus Port Columbus Intl Airport
  • 09:20 (CMH)Columbus Port Columbus Intl Airport
    11:25 (MDW)Chicago Midway Airport
  • (WN 1218)Boeing 737 700
    (WN 3279)Boeing 737 700
  • 05h 20m (01h 50m)
  • CMH Columbus 01h 50m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 07:10 - 08:50
    MCO - STL
    10:00 - 11:05
    STL - MDW
  • 07:10 (MCO)Orlando International Airport
    10:00 (STL)St Louis Lambert Intl Airport
  • 08:50 (STL)St Louis Lambert Intl Airport
    11:05 (MDW)Chicago Midway Airport
  • (WN 4676)Boeing 737 700
    (WN 5866)Boeing 737 Max 8 Passenger
  • 04h 55m (01h 10m)
  • STL Saint Louis 01h 10m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:10 - 09:10
    MCO - AUS
    10:05 - 12:45
    AUS - ORD
  • 07:10 (MCO)Orlando International Airport
    10:05 (AUS)Austin-Bergstrom International Airport
  • 09:10 (AUS)Austin-Bergstrom International Airport
    12:45 (ORD)Chicago O'Hare International Airport
  • (WN 6146)Boeing 737 800
    (WN 5783)Boeing 737 800
  • 06h 35m (00h 55m)
  • AUS Austin 00h 55m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 07:15 - 08:10
    MCO - MSY
    10:45 - 13:05
    MSY - MDW
  • 07:15 (MCO)Orlando International Airport
    10:45 (MSY)New Orleans Louis Armstrong Intl Airport
  • 08:10 (MSY)New Orleans Louis Armstrong Intl Airport
    13:05 (MDW)Chicago Midway Airport
  • (WN 512)Boeing 737 700
    (WN 1434)Boeing 737 700
  • 06h 50m (02h 35m)
  • MSY New Orleans 02h 35m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:20 - 09:15
    MCO - DAL
    11:00 - 13:10
    DAL - MDW
  • 07:20 (MCO)Orlando International Airport
    11:00 (DAL)Dallas/Fort Worth Love Field Airport
  • 09:15 (DAL)Dallas/Fort Worth Love Field Airport
    13:10 (MDW)Chicago Midway Airport
  • (WN 365)Boeing 737 700
    (WN 2148)Boeing 737 Max 8 Passenger
  • 06h 50m (01h 45m)
  • DAL Dallas 01h 45m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:25 - 09:45
    MCO - BWI
    11:55 - 13:05
    BWI - ORD
  • 07:25 (MCO)Orlando International Airport
    11:55 (BWI)Baltimore Washington International Airport
  • 09:45 (BWI)Baltimore Washington International Airport
    13:05 (ORD)Chicago O'Hare International Airport
  • (WN 350)Boeing 737 Max 8 Passenger
    (WN 1090)Boeing 737 700
  • 06h 40m (02h 10m)
  • BWI Baltimore 02h 10m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:30 - 10:21
    MCO - YYZ
    12:00 - 12:54
    YYZ - ORD
  • 07:30 (MCO)Orlando International Airport
    12:00 (YYZ)Toronto Lester B Pearson Intl Airport
  • 10:21 (YYZ)Toronto Lester B Pearson Intl Airport
    12:54 (ORD)Chicago O'Hare International Airport
  • Air Canada (AC 1671)Airbus
    Air Canada (AC 505)Airbus A220 300
  • 06h 24m (01h 39m)
  • YYZ Toronto 01h 39m
    • -
    • -
    • -
    • T
    • -
    • S
    • -
  • 07:30 - 10:21
    MCO - YYZ
    12:00 - 12:54
    YYZ - ORD
  • 07:30 (MCO)Orlando International Airport
    12:00 (YYZ)Toronto Lester B Pearson Intl Airport
  • 10:21 (YYZ)Toronto Lester B Pearson Intl Airport
    12:54 (ORD)Chicago O'Hare International Airport
  • Air Canada (AC 1671)Airbus
    Air Canada (AC 8903)Embraer Emb 175
  • 06h 24m (01h 39m)
  • YYZ Toronto 01h 39m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:30 - 10:21
    MCO - YYZ
    12:00 - 12:54
    YYZ - ORD
  • 07:30 (MCO)Orlando International Airport
    12:00 (YYZ)Toronto Lester B Pearson Intl Airport
  • 10:21 (YYZ)Toronto Lester B Pearson Intl Airport
    12:54 (ORD)Chicago O'Hare International Airport
  • Air Canada (AC 1671)Airbus
    Air Canada (AC 505)Airbus A220 300
  • 06h 24m (01h 39m)
  • YYZ Toronto 01h 39m
    • -
    • -
    • W
    • -
    • F
    • -
    • -
  • 07:30 - 09:05
    MCO - STL
    10:00 - 11:05
    STL - MDW
  • 07:30 (MCO)Orlando International Airport
    10:00 (STL)St Louis Lambert Intl Airport
  • 09:05 (STL)St Louis Lambert Intl Airport
    11:05 (MDW)Chicago Midway Airport
  • (WN 4676)Boeing 737 800
    (WN 5866)Boeing 737 700
  • 04h 35m (00h 55m)
  • STL Saint Louis 00h 55m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:35 - 08:48
    MCO - MIA
    09:49 - 12:16
    MIA - ORD
  • 07:35 (MCO)Orlando International Airport
    09:49 (MIA)Miami International Airport
  • 08:48 (MIA)Miami International Airport
    12:16 (ORD)Chicago O'Hare International Airport
  • American Airlines (AA 2125)Boeing 737 Max 8 Passenger
    American Airlines (AA 2565)Boeing 737 800
  • 05h 41m (01h 01m)
  • MIA Miami 01h 01m
    • -
    • -
    • -
    • -
    • -
    • S
    • S
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What’s the fastest flight time from Orlando to Chicago?

The fastest flight time for direct flights from Orlando to Chicago is 2 hours 43 minutes. Check latest flight schedules & prices on Wego.

What’s the most popular airline flying from Orlando to Chicago?

The most popular airline flying from Orlando to Chicago is Spirit Airlines. Find the latest flight deals on Wego.

How far is Chicago from Orlando?

The flight distance between Orlando and Chicago is 1587km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 00:15. The last flight of the day departs at 23:50. See the full list of flight times on Wego.

How many airlines offer direct flights from Orlando to Chicago?

There are 6 airlines that offer direct flights from Orlando to Chicago. Find out the list of airlines on Wego.