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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 CAD 129 and round-trip from CAD 276. Based on Trip.com's latest 7-day flight data.

      • MCO 06:15
        7h 24m
        1 stop
        MDW 12:39
        Orlando - Chicago | Mon, Oct 5 | Delta Air Lines
        ORD 16:49
        2h 53m
        Direct
        MCO 20:42
        Chicago - Orlando | Wed, Oct 7 | Frontier Airlines
        CAD 276 CAD 379
        27% off
        27% off
        CAD 379 CAD 276
      • MCO 07:10
        4h 48m
        1 stop
        MDW 10:58
        Orlando - Chicago | Mon, Oct 5 | Frontier Airlines
        ORD 16:49
        2h 53m
        Direct
        MCO 20:42
        Chicago - Orlando | Wed, Oct 7 | Frontier Airlines
        CAD 283 CAD 379
        25% off
        25% off
        CAD 379 CAD 283
      • MCO 12:54
        5h 33m
        1 stop
        MDW 17:27
        Orlando - Chicago | Thu, Oct 29 | Frontier Airlines
        ORD 10:26
        5h 58m
        1 stop
        MCO 17:24
        Chicago - Orlando | Sat, Oct 31 | Frontier Airlines
        CAD 284 CAD 379
        25% off
        25% off
        CAD 379 CAD 284
      • MCO 06:00
        6h 59m
        1 stop
        MDW 11:59
        Orlando - Chicago | Mon, Sep 28 | Frontier Airlines
        ORD 11:15
        2h 53m
        Direct
        MCO 15:08
        Chicago - Orlando | Wed, Sep 30 | Frontier Airlines
        CAD 289
        24% off
        CAD 379 CAD 289
      • MCO 16:53
        7h 50m
        1 stop
        MDW 23:43
        Orlando - Chicago | Fri, Oct 16 | Frontier Airlines
        RFD 09:34
        2h 30m
        Direct
        SFB 13:04
        Chicago - Orlando | Fri, Oct 23 | Allegiant Air
        CAD 303
        20% off
        CAD 379 CAD 303
      • MCO 12:52
        5h 53m
        1 stop
        MDW 17:45
        Orlando - Chicago | Sat, Oct 17 | Frontier Airlines
        RFD 09:34
        2h 30m
        Direct
        SFB 13:04
        Chicago - Orlando | Fri, Oct 23 | Allegiant Air
        CAD 303
        20% off
        CAD 379 CAD 303
      • MCO 17:19
        7h 25m
        1 stop
        MDW 23:44
        Orlando - Chicago | Sat, Oct 3 | Frontier Airlines
        ORD 16:35
        8h 10m
        1 stop
        MCO 01:45
        Chicago - Orlando | Mon, Oct 5 | Frontier Airlines
        CAD 319
        16% off
        CAD 379 CAD 319
      • MCO 17:40
        6h 4m
        1 stop
        MDW 22:44
        Orlando - Chicago | Mon, Sep 21 | Delta Air Lines
        ORD 15:50
        2h 56m
        Direct
        MCO 19:46
        Chicago - Orlando | Wed, Sep 23 | Frontier Airlines
        CAD 320
        16% off
        CAD 379 CAD 320
      • MCO 18:40
        4h 53m
        1 stop
        MDW 22:33
        Orlando - Chicago | Mon, Oct 12 | Delta Air Lines
        ORD 20:11
        2h 57m
        Direct
        MCO 00:08
        Chicago - Orlando | Wed, Oct 14 | Frontier Airlines
        CAD 321
        15% off
        CAD 379 CAD 321
      • MCO 12:50
        6h 1m
        1 stop
        MDW 17:51
        Orlando - Chicago | Mon, Sep 21 | Frontier Airlines
        ORD 15:50
        2h 56m
        Direct
        MCO 19:46
        Chicago - Orlando | Wed, Sep 23 | Frontier Airlines
        CAD 325
        14% off
        CAD 379 CAD 325
      • MCO 12:52
        5h 53m
        1 stop
        MDW 17:45
        Orlando - Chicago | Sat, Oct 24 | Frontier Airlines
        RFD 09:34
        2h 30m
        Direct
        SFB 13:04
        Chicago - Orlando | Fri, Oct 30 | Allegiant Air
        CAD 329
        13% off
        CAD 379 CAD 329
      • ORL 13:00
        17h 25m
        1 stop
        CHI 14:00
        Orlando - Chicago | Sun, Sep 20 | Normal Airline
        CHI 15:00
        6h
        Direct
        ORL 16:00
        Chicago - Orlando | Tue, Sep 22 | Normal Airline
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      • MCO 17:03
        7h 44m
        1 stop
        MDW 23:47
        Orlando - Chicago | Wed, Nov 4 | Frontier Airlines
        CAD 129 CAD 189
        32% off
        32% off
        CAD 189 CAD 129
      • MCO 12:50
        6h 1m
        1 stop
        MDW 17:51
        Orlando - Chicago | Wed, Sep 23 | Frontier Airlines
        CAD 133 CAD 189
        30% off
        30% off
        CAD 189 CAD 133
      • MCO 17:03
        7h 44m
        1 stop
        MDW 23:47
        Orlando - Chicago | Sat, Nov 7 | Frontier Airlines
        CAD 135 CAD 189
        28% off
        28% off
        CAD 189 CAD 135
      • MCO 17:03
        7h 44m
        1 stop
        MDW 23:47
        Orlando - Chicago | Tue, Nov 10 | Frontier Airlines
        CAD 137
        28% off
        CAD 189 CAD 137
      • MCO 17:03
        7h 44m
        1 stop
        MDW 23:47
        Orlando - Chicago | Wed, Nov 11 | Frontier Airlines
        CAD 137
        28% off
        CAD 189 CAD 137
      • MCO 12:50
        6h 1m
        1 stop
        MDW 17:51
        Orlando - Chicago | Wed, Oct 7 | Frontier Airlines
        CAD 139
        26% off
        CAD 189 CAD 139
      • MCO 13:15
        5h 30m
        1 stop
        MDW 17:45
        Orlando - Chicago | Thu, Oct 8 | Frontier Airlines
        CAD 139
        26% off
        CAD 189 CAD 139
      • MCO 17:03
        7h 44m
        1 stop
        MDW 23:47
        Orlando - Chicago | Thu, Oct 29 | Frontier Airlines
        CAD 141
        25% off
        CAD 189 CAD 141
      • MCO 12:52
        5h 53m
        1 stop
        MDW 17:45
        Orlando - Chicago | Thu, Oct 22 | Frontier Airlines
        CAD 143
        24% off
        CAD 189 CAD 143
      • MCO 09:25
        9h 22m
        1 stop
        MDW 17:47
        Orlando - Chicago | Sat, Oct 31 | Frontier Airlines
        CAD 143
        24% off
        CAD 189 CAD 143
      • MCO 14:52
        9h 51m
        1 stop
        MDW 23:43
        Orlando - Chicago | Sat, Oct 24 | Frontier Airlines
        CAD 143
        24% off
        CAD 189 CAD 143
      • MCO 09:30
        9h 21m
        1 stop
        MDW 17:51
        Orlando - Chicago | Sat, Sep 26 | Frontier Airlines
        CAD 148
        22% off
        CAD 189 CAD 148
      • ORL 13:00
        17h 25m
        1 stop
        CHI 14:00
        Orlando - Chicago | Sun, Sep 20 | Normal Airline
        Find more flights
        Find more flights

Displayed flight fares from Orlando International Airport to Chicago Midway International Airport are based on average prices across airlines for the next 3 months according to the latest Trip.com data.

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 December, with an average price of CAD 85. It is best to avoid June, when the average price can reach CAD 342.

CAD 342
CAD 214
CAD 85
0
    Cheapest
  • CAD 153
    Sep
  • CAD 98
    Oct
  • CAD 151
    Nov
  • CAD 85
    Dec
  • CAD 163
    Jan
  • CAD 143
    Feb
  • CAD 223
    Mar
  • CAD 132
    Apr
  • CAD 182
    May
  • CAD 342
    Jun
  • CAD 193
    Jul
  • CAD 204
    Aug

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.

CAD 225
CAD 162
CAD 99
CAD 36
  • CAD 152
    Mon
  • CAD 99
    Tue
  • CAD 177
    Wed
  • CAD 225
    Thu
  • CAD 142
    Fri
  • CAD 169
    Sat
  • CAD 208
    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 CAD 123) among 4 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From CAD 123
Delta Air Lines
From CAD 144
Hahn Air
From CAD 199
Sun Country Airlines
From CAD 233

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. DL1150

    Orlando International Airport

    17:40

    MCO

    1h 50m

    Direct

    19:30

    ATL

    S M T W T F S
    Search

  2. DL1076

    Hartsfield–Jackson Atlanta International Airport

    21:15

    ATL

    1h 55m

    Direct

    22:10

    MDW

    S M T W T F S

  3. F93507

    Orlando International Airport

    12:50

    MCO

    1h 45m

    Direct

    14:35

    ATL

    S M T W T F S
    Search

  4. F92779

    Hartsfield–Jackson Atlanta International Airport

    06:01

    ATL

    2h 1m

    Direct

    07:02

    MDW

    S M T W T F S

  5. F94025

    Orlando International Airport

    17:19

    MCO

    1h 54m

    Direct

    19:13

    ATL

    S M T W T F S
    Search

  6. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 54m

    Direct

    23:44

    MDW

    S - - W T - S

  7. DL1201

    Orlando International Airport

    06:20

    MCO

    2h 45m

    Direct

    09:05

    DTW

    S M T W T F S
    Search

  8. DL4688

    Detroit Metropolitan Wayne County Airport

    12:20

    DTW

    1h 19m

    Direct

    12:39

    MDW

    S M T W T F S

  9. F91241

    Orlando International Airport

    09:30

    MCO

    1h 44m

    Direct

    11:14

    ATL

    S M T W T F S
    Search

  10. F92779

    Hartsfield–Jackson Atlanta International Airport

    06:01

    ATL

    2h 1m

    Direct

    07:02

    MDW

    S M T W T F S

  11. F93507

    Orlando International Airport

    12:50

    MCO

    1h 45m

    Direct

    14:35

    ATL

    S M T W T F S
    Search

  12. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 54m

    Direct

    23:44

    MDW

    S - - W T - S

  13. F91563

    Orlando International Airport

    06:50

    MCO

    2h 3m

    Direct

    08:53

    ATL

    S - - W T - S
    Search

  14. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 54m

    Direct

    23:44

    MDW

    S - - W T - S

  15. F94025

    Orlando International Airport

    17:19

    MCO

    1h 54m

    Direct

    19:13

    ATL

    S M T W T F S
    Search

  16. F92779

    Hartsfield–Jackson Atlanta International Airport

    06:01

    ATL

    2h 1m

    Direct

    07:02

    MDW

    S M T W T F 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 distance1,596.77km
Cheapest one-way ticket priceCAD 129
Cheapest return ticket priceCAD 276

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 12 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 8 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 06:55, and the last departs at 20:55, with about 28 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 CAD 387 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 CAD 129, and round-trip fares start from CAD 276. The current lowest fare is a Frontier Airlines flight departing on Wed, Nov 4; 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 CAD 227. 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.