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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 US$62 and round-trip from US$128. Based on Trip.com's latest 7-day flight data.

    • Cheapest nonstop
      MCO 17:39
      3h 1m
      Direct
      MDW 19:40
      Orlando - Chicago | Sat, Dec 19 | Frontier Airlines
      MDW 20:35
      2h 50m
      Direct
      MCO 00:25
      Chicago - Orlando | Tue, Dec 22 | Frontier Airlines
      US$129 US$169
      24% off
      24% off
      US$169 US$129
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Thu, Dec 10 | Frontier Airlines
      ORD 05:35
      2h 54m
      Direct
      MCO 09:29
      Chicago - Orlando | Tue, Dec 15 | Frontier Airlines
      US$133 US$169
      21% off
      21% off
      US$169 US$133
    • MCO 15:14
      3h 2m
      Direct
      MDW 17:16
      Orlando - Chicago | Mon, Dec 7 | Frontier Airlines
      ORD 17:24
      3h 1m
      Direct
      MCO 21:25
      Chicago - Orlando | Sat, Dec 12 | Frontier Airlines
      US$133 US$169
      21% off
      21% off
      US$169 US$133
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Tue, Nov 24 | Frontier Airlines
      MDW 20:42
      2h 43m
      Direct
      MCO 00:25
      Chicago - Orlando | Mon, Nov 30 | Frontier Airlines
      US$140
      17% off
      US$169 US$140
    • MCO 17:29
      3h 1m
      Direct
      MDW 19:30
      Orlando - Chicago | Thu, Dec 17 | Frontier Airlines
      MDW 20:35
      2h 50m
      Direct
      MCO 00:25
      Chicago - Orlando | Mon, Dec 21 | Frontier Airlines
      US$140
      17% off
      US$169 US$140
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      ORD 17:12
      3h
      Direct
      MCO 21:12
      Chicago - Orlando | Wed, Nov 25 | Frontier Airlines
      US$146
      14% off
      US$169 US$146
    • MCO 09:28
      7h 39m
      1 stop
      MDW 16:07
      Orlando - Chicago | Thu, Dec 3 | Frontier Airlines
      ORD 17:24
      3h 1m
      Direct
      MCO 21:25
      Chicago - Orlando | Tue, Dec 8 | Frontier Airlines
      US$128
      24% off
      US$169 US$128
    • MCO 06:00
      6h 22m
      1 stop
      MDW 11:22
      Orlando - Chicago | Tue, Nov 10 | Frontier Airlines
      RFD 10:38
      2h 36m
      Direct
      SFB 14:14
      Chicago - Orlando | Mon, Nov 16 | Allegiant Air
      US$130
      23% off
      US$169 US$130
    • MCO 07:10
      5h 23m
      1 stop
      MDW 11:33
      Orlando - Chicago | Wed, Dec 9 | Frontier Airlines
      ORD 17:24
      3h 1m
      Direct
      MCO 21:25
      Chicago - Orlando | Sat, Dec 12 | Frontier Airlines
      US$137
      19% off
      US$169 US$137
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Tue, Oct 27 | Normal Airline
      CHI 15:00
      6h
      Direct
      ORL 16:00
      Chicago - Orlando | Thu, Oct 29 | Normal Airline
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    • Cheapest
      MCO 12:54
      5h 53m
      1 stop
      MDW 17:47
      Orlando - Chicago | Sun, Nov 8 | Frontier Airlines
      US$62 US$117
      47% off
      47% off
      US$117 US$62
    • Cheapest
      MCO 12:54
      5h 53m
      1 stop
      MDW 17:47
      Orlando - Chicago | Thu, Nov 19 | Frontier Airlines
      US$62 US$117
      47% off
      47% off
      US$117 US$62
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      US$71 US$117
      39% off
      39% off
      US$117 US$71
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Thu, Dec 17 | Frontier Airlines
      US$78
      33% off
      US$117 US$78
    • MCO 07:15
      5h 18m
      1 stop
      MDW 11:33
      Orlando - Chicago | Wed, Dec 16 | Frontier Airlines
      US$78
      33% off
      US$117 US$78
    • MCO 08:07
      10h 40m
      1 stop
      MDW 17:47
      Orlando - Chicago | Fri, Nov 13 | Frontier Airlines
      US$86
      26% off
      US$117 US$86
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      US$87
      26% off
      US$117 US$87
    • MCO 08:07
      10h 40m
      1 stop
      MDW 17:47
      Orlando - Chicago | Fri, Nov 27 | Frontier Airlines
      US$89
      24% off
      US$117 US$89
    • MCO 12:54
      5h 53m
      1 stop
      MDW 17:47
      Orlando - Chicago | Thu, Nov 26 | Frontier Airlines
      US$91
      22% off
      US$117 US$91
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Tue, Oct 27 | Normal Airline
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    • Cheapest nonstop
      MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      US$71 US$117
      39% off
      39% off
      US$117 US$71
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      US$87 US$117
      26% off
      26% off
      US$117 US$87
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Thu, Dec 24 | Frontier Airlines
      US$103 US$217
      53% off
      53% off
      US$217 US$103
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      US$104
      52% off
      US$217 US$104
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      US$129
      41% off
      US$217 US$129
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      US$129
      41% off
      US$217 US$129
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      US$129
      41% off
      US$217 US$129
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      US$150
      31% off
      US$217 US$150
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      US$154
      28% off
      US$217 US$154
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Tue, Oct 27 | 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
      US$71 US$240
      70% off
      70% off
      US$240 US$71
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      US$87 US$240
      64% off
      64% off
      US$240 US$87
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Thu, Dec 24 | Frontier Airlines
      US$103 US$240
      56% off
      56% off
      US$240 US$103
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      US$104
      56% off
      US$240 US$104
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      US$129
      46% off
      US$240 US$129
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      US$129
      46% off
      US$240 US$129
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      US$129
      46% off
      US$240 US$129
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      US$150
      38% off
      US$240 US$150
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      US$154
      36% off
      US$240 US$154
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Tue, Oct 27 | Normal Airline
      Find more flights
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    • MCO 06:35
      4h 28m
      1 stop
      MDW 10:03
      Orlando - Chicago | Tue, Oct 27 | Delta Air Lines
      US$210 US$436
      52% off
      52% off
      US$436 US$210
    • MCO 06:35
      4h 28m
      1 stop
      MDW 10:03
      Orlando - Chicago | Fri, Oct 30 | Delta Air Lines
      US$248 US$436
      43% off
      43% off
      US$436 US$248
    • MCO 14:02
      4h 58m
      1 stop
      MDW 18:00
      Orlando - Chicago | Wed, Oct 28 | Delta Air Lines
      US$388 US$436
      11% off
      11% off
      US$436 US$388
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Tue, Oct 27 | Normal Airline
      Find more flights
      Find more flights
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      US$71 US$117
      39% off
      39% off
      US$117 US$71
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      US$87 US$117
      26% off
      26% off
      US$117 US$87
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Thu, Dec 24 | Frontier Airlines
      US$103 US$217
      53% off
      53% off
      US$217 US$103
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      US$104
      52% off
      US$217 US$104
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      US$129
      41% off
      US$217 US$129
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      US$129
      41% off
      US$217 US$129
    • MCO 17:01
      3h 1m
      Direct
      MDW 19:02
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      US$129
      41% off
      US$217 US$129
    • MCO 17:46
      3h 1m
      Direct
      MDW 19:47
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      US$150
      31% off
      US$217 US$150
    • MCO 17:41
      3h 1m
      Direct
      MDW 19:42
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      US$154
      28% off
      US$217 US$154
    • ORL 13:00
      17h 25m
      1 stop
      CHI 14:00
      Orlando - Chicago | Tue, Oct 27 | Normal Airline
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Displayed flight fares from Orlando to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

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

What is the cheapest month to fly from Orlando International Airport to Chicago Midway International Airport?

The data is based on the past 12 months and shows the average one-way ticket prices from Orlando International Airport to Chicago Midway International Airport for each month in the Trip.com database.

Based on Trip.com's 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 US$54. It is best to avoid June, when the average price can reach US$246.

US$246
US$150
US$54
0
  • US$54
    Oct
  • US$109
    Nov
  • US$61
    Dec
  • US$117
    Jan
  • US$103
    Feb
  • US$160
    Mar
  • US$95
    Apr
  • US$131
    May
  • US$246
    Jun
  • US$139
    Jul
  • US$146
    Aug
  • US$144
    Sep

What is the cheapest day of the week to fly from Orlando International Airport to Chicago Midway International Airport?

The data is based on the past 12 months and shows the average ticket prices from Orlando International Airport to Chicago Midway International Airport for each day of the week in the Trip.com database.

Based on Trip.com's data from the past 12 months, the cheapest departure day from Orlando International Airport to Chicago Midway International Airport is Tuesday, with average prices usually lower than other days. Avoid departing on Thursday as prices are typically highest on that day.

US$199
US$135
US$71
US$7
  • US$120
    Mon
  • US$71
    Tue
  • US$106
    Wed
  • US$199
    Thu
  • US$102
    Fri
  • US$146
    Sat
  • US$153
    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 US$60) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From US$60
Delta Air Lines
From US$114
Hahn Air
From US$126

Find more flights and airlines

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

    06:07

    MCO

    1h 54m

    Direct

    08:01

    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

    - M T W T F S

  3. F93507

    Orlando International Airport

    12:52

    MCO

    1h 44m

    Direct

    14:36

    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

    - M T W T F S

  5. DL2204

    Orlando International Airport

    09:45

    MCO

    1h 40m

    Direct

    11:25

    ATL

    S M T W T F S
    Search

  6. DL1728

    Hartsfield–Jackson Atlanta International Airport

    15:30

    ATL

    1h 55m

    Direct

    16:25

    MDW

    S M T W T F S

  7. F94025

    Orlando International Airport

    16:53

    MCO

    1h 51m

    Direct

    18:44

    ATL

    S M T W T F S
    Search

  8. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - 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. F93975

    Orlando International Airport

    14:52

    MCO

    1h 52m

    Direct

    16:44

    ATL

    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. F91241

    Orlando International Airport

    09:25

    MCO

    1h 50m

    Direct

    11:15

    ATL

    S M T W T F S
    Search

  14. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    - M T W T F S

  15. F91563

    Orlando International Airport

    06:07

    MCO

    1h 54m

    Direct

    08:01

    ATL

    S M T W T F S
    Search

  16. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S

  17. F93507

    Orlando International Airport

    12:52

    MCO

    1h 44m

    Direct

    14:36

    ATL

    S M T W T F S
    Search

  18. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S

  19. F91241

    Orlando International Airport

    09:25

    MCO

    1h 50m

    Direct

    11:15

    ATL

    S M T W T F S
    Search

  20. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S
Find more flights and airlines

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 US$62
Cheapest return ticket price US$128

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 8 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 US$265 in November, the most expensive month to book this route.
    • 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 US$62, and round-trip fares start from US$128. The current lowest fare is a Frontier Airlines flight departing on Sun, Nov 8; 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 US$169. 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.

Find Cheap Flights with Trip.com

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

Book with no extra fees

Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, civil aviation development fund, etc.), with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check 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 according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please visit the customer support pages.