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Orlando Intl. Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Orlando Intl. Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from $59 and round-trip from $128. Based on Trip.com's latest 7-day flight data.

    • Cheapest nonstop
      MCO 5:41 PM
      3h 1m
      Nonstop
      MDW 7:42 PM
      Orlando - Chicago | Thu, Dec 10 | Frontier Airlines
      ORD 5:35 AM
      2h 54m
      Nonstop
      MCO 9:29 AM
      Chicago - Orlando | Tue, Dec 15 | Frontier Airlines
      $133 $203
      34% off
      34% off
      $203 $133
    • MCO 3:14 PM
      3h 2m
      Nonstop
      MDW 5:16 PM
      Orlando - Chicago | Mon, Dec 7 | Frontier Airlines
      ORD 5:24 PM
      3h 1m
      Nonstop
      MCO 9:25 PM
      Chicago - Orlando | Sat, Dec 12 | Frontier Airlines
      $133 $203
      34% off
      34% off
      $203 $133
    • MCO 5:39 PM
      3h 1m
      Nonstop
      MDW 7:40 PM
      Orlando - Chicago | Sat, Dec 19 | Frontier Airlines
      MDW 8:35 PM
      2h 50m
      Nonstop
      MCO 12:25 AM
      Chicago - Orlando | Wed, Dec 23 | Frontier Airlines
      $137 $203
      33% off
      33% off
      $203 $137
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Tue, Nov 24 | Frontier Airlines
      MDW 8:42 PM
      2h 43m
      Nonstop
      MCO 12:25 AM
      Chicago - Orlando | Mon, Nov 30 | Frontier Airlines
      $140
      31% off
      $203 $140
    • MCO 5:29 PM
      3h 1m
      Nonstop
      MDW 7:30 PM
      Orlando - Chicago | Thu, Dec 17 | Frontier Airlines
      MDW 8:35 PM
      2h 50m
      Nonstop
      MCO 12:25 AM
      Chicago - Orlando | Mon, Dec 21 | Frontier Airlines
      $140
      31% off
      $203 $140
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Sat, Nov 21 | Frontier Airlines
      ORD 5:12 PM
      3h
      Nonstop
      MCO 9:12 PM
      Chicago - Orlando | Wed, Nov 25 | Frontier Airlines
      $146
      28% off
      $203 $146
    • MCO 9:28 AM
      7h 39m
      1 stop
      MDW 4:07 PM
      Orlando - Chicago | Thu, Dec 3 | Frontier Airlines
      ORD 5:24 PM
      3h 1m
      Nonstop
      MCO 9:25 PM
      Chicago - Orlando | Tue, Dec 8 | Frontier Airlines
      $128
      37% off
      $203 $128
    • MCO 6:00 AM
      6h 22m
      1 stop
      MDW 11:22 AM
      Orlando - Chicago | Tue, Nov 10 | Frontier Airlines
      RFD 10:38 AM
      2h 36m
      Nonstop
      SFB 2:14 PM
      Chicago - Orlando | Mon, Nov 16 | Allegiant Air
      $130
      36% off
      $203 $130
    • MCO 7:10 AM
      5h 23m
      1 stop
      MDW 11:33 AM
      Orlando - Chicago | Wed, Dec 9 | Frontier Airlines
      ORD 5:24 PM
      3h 1m
      Nonstop
      MCO 9:25 PM
      Chicago - Orlando | Sat, Dec 12 | Frontier Airlines
      $137
      33% off
      $203 $137
    • ORL 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Orlando - Chicago | Mon, Oct 26 | Normal Airline
      CHI 3:00 PM
      6h
      Nonstop
      ORL 4:00 PM
      Chicago - Orlando | Wed, Oct 28 | Normal Airline
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    • Cheapest
      MCO 12:54 PM
      5h 53m
      1 stop
      MDW 5:47 PM
      Orlando - Chicago | Wed, Nov 18 | Frontier Airlines
      $59 $138
      56% off
      56% off
      $138 $59
    • MCO 7:10 AM
      5h 23m
      1 stop
      MDW 11:33 AM
      Orlando - Chicago | Wed, Dec 9 | Frontier Airlines
      $60 $138
      56% off
      56% off
      $138 $60
    • MCO 12:54 PM
      5h 53m
      1 stop
      MDW 5:47 PM
      Orlando - Chicago | Wed, Nov 11 | Frontier Airlines
      $62 $138
      55% off
      55% off
      $138 $62
    • MCO 7:00 AM
      11h 47m
      1 stop
      MDW 5:47 PM
      Orlando - Chicago | Tue, Nov 10 | Frontier Airlines
      $64
      54% off
      $138 $64
    • MCO 5:29 PM
      3h 1m
      Nonstop
      MDW 7:30 PM
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      $71
      49% off
      $138 $71
    • MCO 4:48 PM
      7h 59m
      1 stop
      MDW 11:47 PM
      Orlando - Chicago | Thu, Nov 19 | Frontier Airlines
      $75
      46% off
      $138 $75
    • MCO 7:15 AM
      5h 18m
      1 stop
      MDW 11:33 AM
      Orlando - Chicago | Tue, Dec 8 | Frontier Airlines
      $78
      43% off
      $138 $78
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      $87
      37% off
      $138 $87
    • MCO 9:15 AM
      7h 52m
      1 stop
      MDW 4:07 PM
      Orlando - Chicago | Fri, Dec 4 | Frontier Airlines
      $93
      33% off
      $138 $93
    • ORL 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Orlando - Chicago | Mon, Oct 26 | Normal Airline
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    • Cheapest nonstop
      MCO 5:29 PM
      3h 1m
      Nonstop
      MDW 7:30 PM
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      $71 $138
      49% off
      49% off
      $138 $71
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      $87 $138
      37% off
      37% off
      $138 $87
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Thu, Dec 24 | Frontier Airlines
      $103 $217
      53% off
      53% off
      $217 $103
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      $105
      52% off
      $217 $105
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      $122
      44% off
      $217 $122
    • MCO 5:41 PM
      3h 1m
      Nonstop
      MDW 7:42 PM
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      $122
      44% off
      $217 $122
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      $129
      41% off
      $217 $129
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      $129
      41% off
      $217 $129
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      $129
      41% off
      $217 $129
    • ORL 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Orlando - Chicago | Mon, Oct 26 | Normal Airline
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    • Cheapest nonstop
      MCO 5:29 PM
      3h 1m
      Nonstop
      MDW 7:30 PM
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      $71 $278
      74% off
      74% off
      $278 $71
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      $87 $278
      69% off
      69% off
      $278 $87
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Thu, Dec 24 | Frontier Airlines
      $103 $278
      63% off
      63% off
      $278 $103
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      $105
      62% off
      $278 $105
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      $122
      56% off
      $278 $122
    • MCO 5:41 PM
      3h 1m
      Nonstop
      MDW 7:42 PM
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      $122
      56% off
      $278 $122
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      $129
      54% off
      $278 $129
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      $129
      54% off
      $278 $129
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      $129
      54% off
      $278 $129
    • ORL 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Orlando - Chicago | Mon, Oct 26 | Normal Airline
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    • MCO 6:35 AM
      4h 28m
      1 stop
      MDW 10:03 AM
      Orlando - Chicago | Tue, Oct 27 | Delta Air Lines
      $210 $311
      32% off
      32% off
      $311 $210
    • MCO 2:02 PM
      4h 58m
      1 stop
      MDW 6:00 PM
      Orlando - Chicago | Wed, Oct 28 | Delta Air Lines
      $227 $311
      27% off
      27% off
      $311 $227
    • MCO 6:35 AM
      4h 28m
      1 stop
      MDW 10:03 AM
      Orlando - Chicago | Fri, Oct 30 | Delta Air Lines
      $230 $311
      26% off
      26% off
      $311 $230
    • ORL 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Orlando - Chicago | Mon, Oct 26 | Normal Airline
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    • MCO 5:29 PM
      3h 1m
      Nonstop
      MDW 7:30 PM
      Orlando - Chicago | Wed, Dec 23 | Frontier Airlines
      $71 $138
      49% off
      49% off
      $138 $71
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Wed, Nov 25 | Frontier Airlines
      $87 $138
      37% off
      37% off
      $138 $87
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Thu, Dec 24 | Frontier Airlines
      $103 $217
      53% off
      53% off
      $217 $103
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Fri, Nov 20 | Frontier Airlines
      $105
      52% off
      $217 $105
    • MCO 5:46 PM
      3h 1m
      Nonstop
      MDW 7:47 PM
      Orlando - Chicago | Sun, Nov 22 | Frontier Airlines
      $122
      44% off
      $217 $122
    • MCO 5:41 PM
      3h 1m
      Nonstop
      MDW 7:42 PM
      Orlando - Chicago | Sun, Dec 13 | Frontier Airlines
      $122
      44% off
      $217 $122
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Wed, Dec 30 | Frontier Airlines
      $129
      41% off
      $217 $129
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Tue, Dec 29 | Frontier Airlines
      $129
      41% off
      $217 $129
    • MCO 5:01 PM
      3h 1m
      Nonstop
      MDW 7:02 PM
      Orlando - Chicago | Sat, Dec 26 | Frontier Airlines
      $129
      41% off
      $217 $129
    • ORL 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Orlando - Chicago | Mon, Oct 26 | 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 Intl. Airport to Chicago Midway International Airport

What is the cheapest month for one-way flights from Orlando Intl. Airport to Chicago Midway International Airport?

Data is based on average one-way flight prices from Orlando Intl. Airport to Chicago Midway International Airport in Trip.com's database over the past 12 months.

Based on Trip.com’s data from the past 12 months, if you’re looking for a low-cost one-way ticket from Orlando Intl. Airport to Chicago Midway International Airport, the best time to buy is in October, with an average price of $54. You’ll want to avoid June, when the average price can reach as high as $246.

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

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

The data is based on the past 12 months and shows the average ticket prices from Orlando Intl. 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 day to depart from Orlando Intl. Airport to Chicago Midway International Airport is Tuesday, with average fares typically lower than other days. You’ll want to avoid flying on Thursday, as ticket prices are usually the highest that day.

$199
$135
$71
$7
  • $120
    Mon
  • $71
    Tue
  • $106
    Wed
  • $199
    Thu
  • $102
    Fri
  • $146
    Sat
  • $153
    Sun

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

The cheapest airline flying from Orlando Intl. Airport to Chicago Midway International Airport is Frontier Airlines (from $61) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From $61
Delta Air Lines
From $106
Hahn Air
From $126

Find more flights and airlines

What is the flight schedule from Orlando Intl. 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 Intl. Airport

    6:07 AM

    MCO

    1h 54m

    Nonstop

    8:01 AM

    ATL

    S M T W T F S
    Search

  2. F92779

    Hartsfield–Jackson Atlanta International Airport

    4:44 PM

    ATL

    2h 1m

    Nonstop

    5:45 PM

    MDW

    - M T W T F S

  3. DL2845

    Orlando Intl. Airport

    8:15 AM

    MCO

    2h 45m

    Nonstop

    11:00 AM

    DTW

    S M T W T F S
    Search

  4. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28 PM

    DTW

    1h 19m

    Nonstop

    12:47 PM

    MDW

    S M T W T F S

  5. F93507

    Orlando Intl. Airport

    11:50 AM

    MCO

    1h 43m

    Nonstop

    1:33 PM

    ATL

    S M T W T F S
    Search

  6. F92779

    Hartsfield–Jackson Atlanta International Airport

    4:44 PM

    ATL

    2h 1m

    Nonstop

    5:45 PM

    MDW

    - M T W T F S

  7. DL1201

    Orlando Intl. Airport

    6:05 AM

    MCO

    2h 49m

    Nonstop

    8:54 AM

    DTW

    S M T W T F S
    Search

  8. DL4684

    Detroit Metropolitan Wayne County Airport

    8:25 AM

    DTW

    1h 24m

    Nonstop

    8:49 AM

    MDW

    S M T W T F S

  9. DL1201

    Orlando Intl. Airport

    6:05 AM

    MCO

    2h 49m

    Nonstop

    8:54 AM

    DTW

    S M T W T F S
    Search

  10. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28 PM

    DTW

    1h 19m

    Nonstop

    12:47 PM

    MDW

    S M T W T F S

  11. F94025

    Orlando Intl. Airport

    4:53 PM

    MCO

    1h 51m

    Nonstop

    6:44 PM

    ATL

    S M T W T F S
    Search

  12. F92291

    Hartsfield–Jackson Atlanta International Airport

    10:45 PM

    ATL

    1h 58m

    Nonstop

    11:43 PM

    MDW

    S M T W T - S

  13. F91563

    Orlando Intl. Airport

    6:07 AM

    MCO

    1h 54m

    Nonstop

    8:01 AM

    ATL

    S M T W T F S
    Search

  14. F92291

    Hartsfield–Jackson Atlanta International Airport

    10:45 PM

    ATL

    1h 58m

    Nonstop

    11:43 PM

    MDW

    S M T W T - S

  15. F93975

    Orlando Intl. Airport

    2:52 PM

    MCO

    1h 52m

    Nonstop

    4:44 PM

    ATL

    S - - - - - -
    Search

  16. F92291

    Hartsfield–Jackson Atlanta International Airport

    10:45 PM

    ATL

    1h 58m

    Nonstop

    11:43 PM

    MDW

    S M T W T - S

  17. F91241

    Orlando Intl. Airport

    7:10 AM

    MCO

    1h 52m

    Nonstop

    9:02 AM

    ATL

    S M T W T F S
    Search

  18. F92779

    Hartsfield–Jackson Atlanta International Airport

    4:44 PM

    ATL

    2h 1m

    Nonstop

    5:45 PM

    MDW

    - M T W T F S

  19. F91241

    Orlando Intl. Airport

    7:10 AM

    MCO

    1h 52m

    Nonstop

    9:02 AM

    ATL

    S M T W T F S
    Search

  20. F92291

    Hartsfield–Jackson Atlanta International Airport

    10:45 PM

    ATL

    1h 58m

    Nonstop

    11:43 PM

    MDW

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

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

Flight distance 1,596.77 km
Cheapest one-way ticket price $59
Cheapest return ticket price $128

FAQs for Orlando Intl. Airport to Chicago Midway International Airport Flights

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

    Orlando Intl. 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 Intl. Airport (MCO) to Chicago Midway International Airport (MDW).
  • The earliest flight from Orlando Intl. 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 Intl. Airport (MCO) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around $265 in November, the most expensive month to book this route.
  • The earliest flight departs from Orlando Intl. Airport (MCO) at 06:35 and arrives in Chicago Midway International Airport (MDW) at 08:32.
  • The latest flight departs from Orlando Intl. Airport (MCO) at 21:33 and arrives in Chicago Midway International Airport (MDW) at 23:29.
    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • Frontier Airlines is a very popular airline operating an average of 6664 flights per month.
  • One-way flights from Orlando Intl. Airport to Chicago Midway International Airport currently start from $59, and round-trip fares start from $128. 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 Intl. Airport to Chicago Midway International Airport is $169. Prices may vary depending on the departure date, airline, and availability.
  • Enter Orlando Intl. 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 estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, 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 were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled 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 check the customer support pages.