Flights from Orlando Airport MCO to Chicago Airport MDW

We've found the cheapest flights to Chicago

Returns from £59.78

One-way from £29.14

A variety of 3 airline companies have direct flights to Midway to Orlando International, Frontier, Volaris and Southwest Airlines. The flight time from Orlando International to Midway is around 2 Hours 41 Minutes and you will cover 1,595 Km (991 Miles). The airport code for Orlando International is MCO and for Midway it is MDW.

Ticket prices are normally at a premium at weekends and can vary also with the time of day. If you are looking to get the cheapest flights possible then we recommend you travel mid week or in the late evening. On occasions, airliners may have special offers so look out for these. We recommend booking your flights to Midway United States in advance as prices normally increase the nearer the departure date.

Please note that the time difference at Midway is 6.0 GMT. So remember to change your watch before arriving at Midway.

Please see below the airlines that fly from Orlando International (MCO) to Midway (MDW) and the amount of daily flights in operation.

Flights Chart
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines777779806:3521:40VIEW FLIGHTS
Volaris100221108:5016:20VIEW FLIGHTS
Frontier100111108:5014:34VIEW FLIGHTS

The most direct flights offered from Orlando International to Midway United States are by Southwest Airlines with around 52 flights a week. These operate from 06:35 with the latest flight being at 21:40. The most popular flight no is WN1345, WN1488, WN1544 and WN1558.

When travelling with Southwest Airlines it would be worth visiting their website www.southwest.com/?ref=southwestairlines.com for further information on bookings and special offers.

Below you can see the times of all flights. These flight times do vary so we recommend you look on the appropriate airline website for accurate information for the dates you are departing.

Flights Time In WeekDays
DayFlight TimesFlights
Monday
06:35
AirlineFlightNo
Southwest AirlinesWN3370
08:20
AirlineFlightNo
Southwest AirlinesWN3713
10:10
AirlineFlightNo
Southwest AirlinesWN3346
14:34
AirlineFlightNo
VolarisY42688
FrontierF93853
15:00
AirlineFlightNo
Southwest AirlinesWN3714
17:30
AirlineFlightNo
Southwest AirlinesWN3715
19:30
AirlineFlightNo
Southwest AirlinesWN2442
21:40
AirlineFlightNo
Southwest AirlinesWN3620
VIEW FLIGHTS
Tuesday
07:20
AirlineFlightNo
Southwest AirlinesWN3370
09:50
AirlineFlightNo
Southwest AirlinesWN626
12:15
AirlineFlightNo
Southwest AirlinesWN1544
14:55
AirlineFlightNo
Southwest AirlinesWN1345
16:35
AirlineFlightNo
Southwest AirlinesWN3713
17:50
AirlineFlightNo
Southwest AirlinesWN3715
20:50
AirlineFlightNo
Southwest AirlinesWN1488
VIEW FLIGHTS
Wednesday
07:20
AirlineFlightNo
Southwest AirlinesWN3370
09:50
AirlineFlightNo
Southwest AirlinesWN626
12:15
AirlineFlightNo
Southwest AirlinesWN1544
14:55
AirlineFlightNo
Southwest AirlinesWN1345
16:35
AirlineFlightNo
Southwest AirlinesWN3713
17:50
AirlineFlightNo
Southwest AirlinesWN3715
20:50
AirlineFlightNo
Southwest AirlinesWN1488
VIEW FLIGHTS
Thursday
06:35
AirlineFlightNo
Southwest AirlinesWN3370
08:20
AirlineFlightNo
Southwest AirlinesWN3713
08:50
AirlineFlightNo
VolarisY42688
FrontierF93853
10:10
AirlineFlightNo
Southwest AirlinesWN3346
10:46
AirlineFlightNo
VolarisY42669
15:00
AirlineFlightNo
Southwest AirlinesWN3714
17:30
AirlineFlightNo
Southwest AirlinesWN3715
19:30
AirlineFlightNo
Southwest AirlinesWN2442
21:40
AirlineFlightNo
Southwest AirlinesWN3620
VIEW FLIGHTS
Friday
06:35
AirlineFlightNo
Southwest AirlinesWN3370
08:20
AirlineFlightNo
Southwest AirlinesWN3713
10:10
AirlineFlightNo
Southwest AirlinesWN3346
14:26
AirlineFlightNo
VolarisY42669
FrontierF93853
15:00
AirlineFlightNo
Southwest AirlinesWN3714
16:20
AirlineFlightNo
VolarisY42688
17:30
AirlineFlightNo
Southwest AirlinesWN3715
19:30
AirlineFlightNo
Southwest AirlinesWN2442
21:40
AirlineFlightNo
Southwest AirlinesWN3620
VIEW FLIGHTS
Saturday
07:10
AirlineFlightNo
Southwest AirlinesWN223
08:25
AirlineFlightNo
VolarisY42669
FrontierF93853
09:20
AirlineFlightNo
Southwest AirlinesWN3713
10:20
AirlineFlightNo
Southwest AirlinesWN1806
11:40
AirlineFlightNo
Southwest AirlinesWN6581
13:10
AirlineFlightNo
Southwest AirlinesWN3860
15:40
AirlineFlightNo
Southwest AirlinesWN3714
16:40
AirlineFlightNo
Southwest AirlinesWN966
18:10
AirlineFlightNo
Southwest AirlinesWN3715
19:15
AirlineFlightNo
Southwest AirlinesWN2442
VIEW FLIGHTS
Sunday
06:50
AirlineFlightNo
Southwest AirlinesWN223
09:10
AirlineFlightNo
VolarisY42669
FrontierF93853
09:30
AirlineFlightNo
Southwest AirlinesWN1544
10:55
AirlineFlightNo
Southwest AirlinesWN1806
14:00
AirlineFlightNo
Southwest AirlinesWN3714
15:45
AirlineFlightNo
Southwest AirlinesWN1673
18:55
AirlineFlightNo
Southwest AirlinesWN3715
19:59
AirlineFlightNo
Southwest AirlinesWN2442
21:25
AirlineFlightNo
Southwest AirlinesWN1558
VIEW FLIGHTS

Alternatively, there are other routes that depart Orlando International and arrive at Midway or other nearby airports. The table below gives you a summary of these.

Alternative Direct Routes
RouteStopsDistanceFlying Time
Gainesville Regional to Chicago Midway01,432 km (890 miles)2 Hours 30 Minutes
Jacksonville to Chicago Midway01,368 km (850 miles)2 Hours 25 Minutes
Punta Gorda Charlotte County to Chicago Midway01,734 km (1,078 miles)2 Hours 51 Minutes
Sarasota to Chicago Midway01,668 km (1,037 miles)2 Hours 46 Minutes
Stuart to Chicago Midway01,763 km (1,095 miles)2 Hours 53 Minutes
Tampa to Chicago Midway01,607 km (998 miles)2 Hours 42 Minutes

If you require a hire car at Midway be sure that you are in possession of a valid driving licence and also a current credit card.

Looking for the best deals on rental cars?

Find cheap hire cars in Orlando

Flight Price FAQ - Orlando (MCO) to Chicago (MDW)

DIRECT Frontier Airlines
What is the cheapest direct flight one way from Orlando MCO to Chicago MDW?
The cheapest direct flight one way from Orlando MCO to Chicago MDW is £29.14 ($39 €33.57)
£29.14
$39 | €33.57
Check Latest Price
DIRECT Frontier Airlines
What is the cheapest direct return flight from Orlando MCO to Chicago MDW?
The cheapest direct return flight from Orlando MCO to Chicago MDW is £59.78 ($80 €68.87)
£59.78
$80 | €68.87
Check Latest Price
Important Note: Prices shown are taken from searches performed for flights operating during the current month. Please use the "Latest Price" buttons to get the most up to date airfares.

Compare Flight Prices from MCO to MDW

Was your flight delayed or cancelled?

Was your flight delayed or cancelled?

You may be eligible to receive up to 600 EUR compensation per person in your party.

Claim Now!

Flight Info FAQ - Orlando (MCO) to Chicago (MDW)

Who flies from Orlando to Chicago?
The following airlines fly from Orlando (MCO) to Chicago (MDW): Frontier, Southwest Airlines, Volaris.
How far is the flight from Orlando to Chicago?
The flight from Orlando to Chicago is 1,595KM or 991 miles.
How long does the flight from Orlando to Chicago to take?
The flight from Orlando to Chicago takes 2 Hours 41 Minutes.

Alternative Airports in United States with Connections from Orlando Airport

Planning a Holiday or Business Trip?

Find cheap hire cars in Orlando, United States

Useful Information about Orlando Airport

New Q1 Passenger Record Set at Orlando Airport - Up 11% on Pre-Pandemic Numbers

Orlando Airport achieved a new record in passenger numbers during the second quarter. Compared to pre-pandemic figures, there was an increase of 11%. When compared to the same period last year, the rise in passenger numbers was even greater, reaching 21%.

View...
Lounges at Orlando Airport

See all the airport lounges, locations and opening times available at Orlando Airport

View...
Eating and Drinking at Orlando Airport

See all bars and restaurants at Orlando Airport, including locations and if they are before or after check-in

View...
Duty Free Shopping at Orlando Airport

See all shops available at Orlando Airport - plan your duty free shopping in advance

View...