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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 SAR 219 and round-trip from SAR 596. 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
      SAR 219 SAR 525
      57% off
      57% off
      SAR 525 SAR 219
    • MCO 07:10
      5h 23m
      1 stop
      MDW 11:33
      Orlando - Chicago | Wed, Dec 9 | Frontier Airlines
      SAR 224 SAR 525
      56% off
      56% off
      SAR 525 SAR 224
    • MCO 12:54
      5h 53m
      1 stop
      MDW 17:47
      Orlando - Chicago | Wed, Nov 11 | Frontier Airlines
      SAR 231 SAR 525
      56% off
      56% off
      SAR 525 SAR 231
    • MCO 07:00
      11h 47m
      1 stop
      MDW 17:47
      Orlando - Chicago | Tue, Nov 10 | Frontier Airlines
      SAR 237
      55% off
      SAR 525 SAR 237
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Tue, Dec 8 | Frontier Airlines
      SAR 293
      44% off
      SAR 525 SAR 293
    • MCO 17:34
      3h 1m
      Direct
      MDW 19:35
      Orlando - Chicago | Thu, Jan 7 | Frontier Airlines
      SAR 299
      72% off
      SAR 1,072 SAR 299
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      SAR 325
      38% off
      SAR 525 SAR 325
    • MCO 09:15
      7h 52m
      1 stop
      MDW 16:07
      Orlando - Chicago | Fri, Dec 4 | Frontier Airlines
      SAR 349
      34% off
      SAR 525 SAR 349
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Tue, Dec 1 | Frontier Airlines
      SAR 371
      28% off
      SAR 525 SAR 371
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
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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
      SAR 674 SAR 992
      32% off
      32% off
      SAR 992 SAR 674
    • 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
      SAR 724 SAR 992
      27% off
      27% off
      SAR 992 SAR 724
    • 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
      SAR 596 SAR 992
      40% off
      40% off
      SAR 992 SAR 596
    • 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
      SAR 612
      38% off
      SAR 992 SAR 612
    • 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
      SAR 633
      36% off
      SAR 992 SAR 633
    • 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
      SAR 646
      35% off
      SAR 992 SAR 646
    • 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
      SAR 655
      34% off
      SAR 992 SAR 655
    • 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
      SAR 662
      33% off
      SAR 992 SAR 662
    • 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
      SAR 664
      33% off
      SAR 992 SAR 664
    • 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 17:34
      3h 1m
      Direct
      MDW 19:35
      Orlando - Chicago | Thu, Jan 7 | Frontier Airlines
      SAR 299 SAR 1,072
      72% off
      72% off
      SAR 1,072 SAR 299
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      SAR 325 SAR 525
      38% off
      38% off
      SAR 525 SAR 325
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 22 | Frontier Airlines
      SAR 382 SAR 1,072
      64% off
      64% off
      SAR 1,072 SAR 382
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      SAR 456
      56% off
      SAR 1,072 SAR 456
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      SAR 482
      55% off
      SAR 1,072 SAR 482
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      SAR 496
      54% off
      SAR 1,072 SAR 496
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      SAR 578
      46% off
      SAR 1,072 SAR 578
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      SAR 579
      46% off
      SAR 1,072 SAR 579
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Mon, Dec 21 | Frontier Airlines
      SAR 583
      46% off
      SAR 1,072 SAR 583
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
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    • Cheapest nonstop
      MCO 17:34
      3h 1m
      Direct
      MDW 19:35
      Orlando - Chicago | Thu, Jan 7 | Frontier Airlines
      SAR 299 SAR 1,098
      73% off
      73% off
      SAR 1,098 SAR 299
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      SAR 325 SAR 1,098
      70% off
      70% off
      SAR 1,098 SAR 325
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 22 | Frontier Airlines
      SAR 382 SAR 1,098
      65% off
      65% off
      SAR 1,098 SAR 382
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      SAR 456
      57% off
      SAR 1,098 SAR 456
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      SAR 482
      56% off
      SAR 1,098 SAR 482
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      SAR 496
      55% off
      SAR 1,098 SAR 496
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      SAR 578
      47% off
      SAR 1,098 SAR 578
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      SAR 579
      47% off
      SAR 1,098 SAR 579
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Mon, Dec 21 | Frontier Airlines
      SAR 583
      47% off
      SAR 1,098 SAR 583
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Fri, Oct 30 | Normal Airline
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    • MCO 06:35
      4h 28m
      1 stop
      MDW 10:03
      Orlando - Chicago | Fri, Oct 30 | Delta Air Lines
      SAR 863 SAR 1,237
      30% off
      30% off
      SAR 1,237 SAR 863
    • 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 17:34
      3h 1m
      Direct
      MDW 19:35
      Orlando - Chicago | Thu, Jan 7 | Frontier Airlines
      SAR 299 SAR 1,072
      72% off
      72% off
      SAR 1,072 SAR 299
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      SAR 325 SAR 525
      38% off
      38% off
      SAR 525 SAR 325
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 22 | Frontier Airlines
      SAR 382 SAR 1,072
      64% off
      64% off
      SAR 1,072 SAR 382
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      SAR 456
      56% off
      SAR 1,072 SAR 456
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      SAR 482
      55% off
      SAR 1,072 SAR 482
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      SAR 496
      54% off
      SAR 1,072 SAR 496
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      SAR 578
      46% off
      SAR 1,072 SAR 578
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      SAR 579
      46% off
      SAR 1,072 SAR 579
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Mon, Dec 21 | Frontier Airlines
      SAR 583
      46% off
      SAR 1,072 SAR 583
    • 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 SAR 203. June sees the highest fares, around SAR 921.

SAR 921
SAR 562
SAR 203
0
  • SAR 203
    Oct
  • SAR 408
    Nov
  • SAR 229
    Dec
  • SAR 438
    Jan
  • SAR 384
    Feb
  • SAR 601
    Mar
  • SAR 356
    Apr
  • SAR 489
    May
  • SAR 921
    Jun
  • SAR 519
    Jul
  • SAR 549
    Aug
  • SAR 539
    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.

SAR 747
SAR 507
SAR 266
SAR 26
  • SAR 449
    Mon
  • SAR 266
    Tue
  • SAR 395
    Wed
  • SAR 747
    Thu
  • SAR 382
    Fri
  • SAR 546
    Sat
  • SAR 574
    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 SAR 227) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From SAR 227
Delta Air Lines
From SAR 374
Hahn Air
From SAR 721

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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. F91563

    Orlando International Airport

    05:25

    MCO

    1h 49m

    Direct

    07:14

    ATL

    S M T W T F S
    Search

  2. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  3. F93507

    Orlando International Airport

    12:54

    MCO

    1h 47m

    Direct

    14:41

    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. F91241

    Orlando International Airport

    06:07

    MCO

    2h 12m

    Direct

    08:19

    ATL

    S M T W T F S
    Search

  6. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  7. DL2204

    Orlando International Airport

    09:45

    MCO

    1h 40m

    Direct

    11:25

    ATL

    S M T W T F S
    Search

  8. DL1728

    Hartsfield–Jackson Atlanta International Airport

    15:30

    ATL

    1h 55m

    Direct

    16:25

    MDW

    S M T W T F S

  9. DL1201

    Orlando International Airport

    06:05

    MCO

    2h 49m

    Direct

    08:54

    DTW

    S M T W T F S
    Search

  10. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Direct

    12:47

    MDW

    S M T W T F S

  11. F94025

    Orlando International Airport

    17:03

    MCO

    1h 48m

    Direct

    18:51

    ATL

    S M T W T F S
    Search

  12. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S

  13. F91563

    Orlando International Airport

    05:25

    MCO

    1h 49m

    Direct

    07:14

    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

  15. F94025

    Orlando International Airport

    17:03

    MCO

    1h 48m

    Direct

    18:51

    ATL

    S M T W T F S
    Search

  16. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F 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 SAR 219
Cheapest return ticket price SAR 596

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 6 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 SAR 1,086 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 SAR 219, and round-trip fares start from SAR 596. 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 SAR 635. 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.