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Orlando International Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Orlando International Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from MYR 239 and round-trip from MYR 649. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      MCO 12:54
      5h 53m
      1 stop
      MDW 17:47
      Orlando - Chicago | Wed, Nov 18 | Frontier Airlines
      MYR 239 MYR 572
      57% off
      57% off
      MYR 572 MYR 239
    • MCO 07:10
      5h 23m
      1 stop
      MDW 11:33
      Orlando - Chicago | Wed, Dec 9 | Frontier Airlines
      MYR 244 MYR 572
      56% off
      56% off
      MYR 572 MYR 244
    • MCO 12:54
      5h 53m
      1 stop
      MDW 17:47
      Orlando - Chicago | Wed, Nov 11 | Frontier Airlines
      MYR 251 MYR 572
      56% off
      56% off
      MYR 572 MYR 251
    • MCO 07:00
      11h 47m
      1 stop
      MDW 17:47
      Orlando - Chicago | Tue, Nov 10 | Frontier Airlines
      MYR 259
      55% off
      MYR 572 MYR 259
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Tue, Dec 8 | Frontier Airlines
      MYR 319
      44% off
      MYR 572 MYR 319
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      MYR 354
      38% off
      MYR 572 MYR 354
    • MCO 09:15
      7h 52m
      1 stop
      MDW 16:07
      Orlando - Chicago | Fri, Dec 4 | Frontier Airlines
      MYR 380
      34% off
      MYR 572 MYR 380
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Tue, Dec 1 | Frontier Airlines
      MYR 405
      28% off
      MYR 572 MYR 405
    • MCO 07:10
      5h 23m
      1 stop
      MDW 11:33
      Orlando - Chicago | Sat, Dec 5 | Frontier Airlines
      MYR 405
      28% off
      MYR 572 MYR 405
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
      Find more flights
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    • Cheapest nonstop
      MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      ORD 05:40
      2h 51m
      Direct
      MCO 09:31
      Chicago - Orlando | Tue, Nov 24 | Frontier Airlines
      MYR 735 MYR 1,081
      32% off
      32% off
      MYR 1,081 MYR 735
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      ORD 05:35
      2h 51m
      Direct
      MCO 09:26
      Chicago - Orlando | Tue, Dec 1 | Frontier Airlines
      MYR 789 MYR 1,081
      27% off
      27% off
      MYR 1,081 MYR 789
    • MCO 09:28
      7h 39m
      1 stop
      MDW 16:07
      Orlando - Chicago | Fri, Dec 11 | Frontier Airlines
      ORD 08:30
      11h 23m
      1 stop
      MCO 20:53
      Chicago - Orlando | Thu, Dec 17 | Frontier Airlines
      MYR 649 MYR 1,081
      40% off
      40% off
      MYR 1,081 MYR 649
    • MCO 07:10
      5h 23m
      1 stop
      MDW 11:33
      Orlando - Chicago | Thu, Dec 17 | Frontier Airlines
      MDW 17:02
      5h 25m
      1 stop
      MCO 23:27
      Chicago - Orlando | Tue, Dec 22 | Frontier Airlines
      MYR 667
      38% off
      MYR 1,081 MYR 667
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Thu, Dec 10 | Frontier Airlines
      MDW 17:02
      6h 11m
      1 stop
      MCO 00:13
      Chicago - Orlando | Sat, Dec 12 | Frontier Airlines
      MYR 690
      36% off
      MYR 1,081 MYR 690
    • MCO 09:10
      7h 56m
      1 stop
      MDW 16:06
      Orlando - Chicago | Fri, Dec 18 | Frontier Airlines
      MDW 17:02
      5h 25m
      1 stop
      MCO 23:27
      Chicago - Orlando | Tue, Dec 22 | Frontier Airlines
      MYR 703
      35% off
      MYR 1,081 MYR 703
    • MCO 07:10
      9h 56m
      1 stop
      MDW 16:06
      Orlando - Chicago | Sat, Dec 19 | Frontier Airlines
      MDW 12:28
      7h 25m
      1 stop
      MCO 20:53
      Chicago - Orlando | Wed, Dec 23 | Frontier Airlines
      MYR 714
      34% off
      MYR 1,081 MYR 714
    • MCO 11:58
      6h 49m
      1 stop
      MDW 17:47
      Orlando - Chicago | Sun, Nov 15 | Frontier Airlines
      RFD 15:34
      2h 36m
      Direct
      SFB 19:10
      Chicago - Orlando | Thu, Nov 19 | Allegiant Air
      MYR 721
      33% off
      MYR 1,081 MYR 721
    • MCO 06:00
      6h 22m
      1 stop
      MDW 11:22
      Orlando - Chicago | Wed, Nov 18 | Frontier Airlines
      RFD 09:28
      2h 36m
      Direct
      SFB 13:04
      Chicago - Orlando | Sat, Nov 21 | Allegiant Air
      MYR 723
      33% off
      MYR 1,081 MYR 723
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
      CHI 15:00
      6h
      Direct
      ORL 16:00
      Chicago - Orlando | Sun, Nov 1 | Normal Airline
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    • Cheapest nonstop
      MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      MYR 354 MYR 572
      38% off
      38% off
      MYR 572 MYR 354
    • MCO 17:29
      3h 1m
      Direct
      MDW 19:30
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      MYR 479 MYR 914
      48% off
      48% off
      MYR 914 MYR 479
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      MYR 497 MYR 914
      46% off
      46% off
      MYR 914 MYR 497
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      MYR 498
      46% off
      MYR 914 MYR 498
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      MYR 525
      43% off
      MYR 914 MYR 525
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      MYR 525
      43% off
      MYR 914 MYR 525
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      MYR 525
      43% off
      MYR 914 MYR 525
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      MYR 540
      41% off
      MYR 914 MYR 540
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      MYR 629
      31% off
      MYR 914 MYR 629
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
      Find more flights
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    • Cheapest nonstop
      MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      MYR 354 MYR 1,196
      70% off
      70% off
      MYR 1,196 MYR 354
    • MCO 17:29
      3h 1m
      Direct
      MDW 19:30
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      MYR 479 MYR 1,196
      60% off
      60% off
      MYR 1,196 MYR 479
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      MYR 497 MYR 1,196
      57% off
      57% off
      MYR 1,196 MYR 497
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      MYR 498
      57% off
      MYR 1,196 MYR 498
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      MYR 525
      56% off
      MYR 1,196 MYR 525
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      MYR 525
      56% off
      MYR 1,196 MYR 525
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      MYR 525
      56% off
      MYR 1,196 MYR 525
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      MYR 540
      55% off
      MYR 1,196 MYR 540
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      MYR 629
      47% off
      MYR 1,196 MYR 629
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
      Find more flights
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    • MCO 06:35
      4h 28m
      1 stop
      MDW 10:03
      Orlando - Chicago | Fri, Oct 30 | Delta Air Lines
      MYR 940 MYR 1,348
      30% off
      30% off
      MYR 1,348 MYR 940
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
      Find more flights
      Find more flights
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      MYR 354 MYR 572
      38% off
      38% off
      MYR 572 MYR 354
    • MCO 17:29
      3h 1m
      Direct
      MDW 19:30
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      MYR 479 MYR 914
      48% off
      48% off
      MYR 914 MYR 479
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      MYR 497 MYR 914
      46% off
      46% off
      MYR 914 MYR 497
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      MYR 498
      46% off
      MYR 914 MYR 498
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      MYR 525
      43% off
      MYR 914 MYR 525
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      MYR 525
      43% off
      MYR 914 MYR 525
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      MYR 525
      43% off
      MYR 914 MYR 525
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      MYR 540
      41% off
      MYR 914 MYR 540
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      MYR 629
      31% off
      MYR 914 MYR 629
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Trip.com Price Insights: Flights from Orlando International Airport to Chicago Midway International Airport

Which month has the cheapest one-way flights from Orlando International Airport to Chicago Midway International Airport?

The data is based on Trip.com data from the past 12 months and shows the average one-way fares by month from Orlando International Airport to Chicago Midway International Airport.

Based on Trip.com data from the past 12 months, the cheapest one-way flights from Orlando International Airport to Chicago Midway International Airport are usually in October, with an average price of MYR 221. June sees the highest fares, around MYR 1,003.

MYR 1,003
MYR 612
MYR 221
0
  • MYR 221
    Oct
  • MYR 444
    Nov
  • MYR 249
    Dec
  • MYR 477
    Jan
  • MYR 419
    Feb
  • MYR 654
    Mar
  • MYR 387
    Apr
  • MYR 533
    May
  • MYR 1,003
    Jun
  • MYR 565
    Jul
  • MYR 598
    Aug
  • MYR 587
    Sep

Which day of the week has the cheapest flights from Orlando International Airport to Chicago Midway International Airport?

The data is based on Trip.com data from the past 12 months and shows the average fares by each day of the week from Orlando International Airport to Chicago Midway International Airport.

Based on Trip.com data from the past 12 months, the cheapest day for flights from Orlando International Airport to Chicago Midway International Airport is Tuesday, with average prices lower than other days. Try to avoid departing on Thursday, as fares are typically the highest.

MYR 814
MYR 552
MYR 290
MYR 28
  • MYR 489
    Mon
  • MYR 290
    Tue
  • MYR 430
    Wed
  • MYR 814
    Thu
  • MYR 416
    Fri
  • MYR 595
    Sat
  • MYR 625
    Sun

Which airline offers the cheapest flights from Orlando International Airport to Chicago Midway International Airport?

The cheapest airline flying from Orlando International Airport to Chicago Midway International Airport is Frontier Airlines (from MYR 248) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From MYR 248
Delta Air Lines
From MYR 407
Hahn Air
From MYR 785

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What is the flight schedule from Orlando International Airport to Chicago Midway International Airport?

Check the schedule for flights from Orlando to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. F94025

    Orlando International Airport

    17:03

    MCO

    1h 48m

    Direct

    18:51

    ATL

    S M T W T F S
    Search

  2. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S

  3. F91563

    Orlando International Airport

    07:04

    MCO

    1h 58m

    Direct

    09:02

    ATL

    S M T W T F S
    Search

  4. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  5. DL2845

    Orlando International Airport

    08:15

    MCO

    2h 45m

    Direct

    11:00

    DTW

    S M T W T F S
    Search

  6. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Direct

    12:47

    MDW

    S M T W T F S

  7. F93507

    Orlando International Airport

    12:54

    MCO

    1h 47m

    Direct

    14:41

    ATL

    S M T W T F S
    Search

  8. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  9. F91241

    Orlando International Airport

    06:07

    MCO

    2h 12m

    Direct

    08:19

    ATL

    S M T W T F S
    Search

  10. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  11. DL1201

    Orlando International Airport

    06:05

    MCO

    2h 49m

    Direct

    08:54

    DTW

    S M T W T F S
    Search

  12. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Direct

    12:47

    MDW

    S M T W T F S

  13. F91563

    Orlando International Airport

    07:04

    MCO

    1h 58m

    Direct

    09:02

    ATL

    S M T W T F S
    Search

  14. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S
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About Orlando International Airport and Chicago Midway International Airport

Learn about Orlando International Airport (MCO) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 1,596.77km
Cheapest one-way ticket price MYR 239
Cheapest return ticket price MYR 649

FAQs for Orlando International Airport to Chicago Midway International Airport Flights

  • How long is the flight from Orlando International Airport to Chicago Midway International Airport?

    Orlando International Airport to Chicago Midway International Airport takes about 3 hours 14 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 5 daily flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW).
  • The earliest flight from Orlando International Airport to Chicago Midway International Airport departs at 06:20, and the last departs at 22:35, with about 37 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
  • The route from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around MYR 1,136 in November, the most expensive month to book this route.
  • The earliest flight departs from Orlando International Airport (MCO) at 07:35 and arrives in Chicago Midway International Airport (MDW) at 09:31.
  • The latest flight departs from Orlando International Airport (MCO) at 17:47 and arrives in Chicago Midway International Airport (MDW) at 19:42.
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.
  • Frontier Airlines is a very popular airline operating an average of 6664 flights per month.
  • One-way flights from Orlando International Airport to Chicago Midway International Airport currently start from MYR 239, and round-trip fares start from MYR 649. The current lowest fare is a Frontier Airlines flight departing on Wed, Nov 18; prices may vary depending on availability.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Orlando International Airport to Chicago Midway International Airport is MYR 691. Prices may vary depending on the departure date, airline, and availability.
  • Enter Orlando International Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

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Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.