Flights from Orlando Airport MCO to Chicago Airport MDW

We've found the cheapest flights to Chicago

Returns from £50.57

One-way from £23.45

A variety of 3 airline companies have direct flights to Midway to Orlando International, Volaris, Frontier 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 Airlines026877706:5022:25VIEW FLIGHTS
Volaris000111112:2014:26VIEW FLIGHTS
Frontier000111112:2014:26VIEW FLIGHTS

The most direct flights offered from Orlando International to Midway United States are by Southwest Airlines with around 37 flights a week. These operate from 06:50 with the latest flight being at 22:25. The most popular flight no is WN1057, WN1674, WN1733 and WN2570.

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
Tuesday
18:40
AirlineFlightNo
Southwest AirlinesWN1733
21:00
AirlineFlightNo
Southwest AirlinesWN4193
VIEW FLIGHTS
Wednesday
09:20
AirlineFlightNo
Southwest AirlinesWN1674
09:25
AirlineFlightNo
Southwest AirlinesWN2570
11:50
AirlineFlightNo
Southwest AirlinesWN4968
14:35
AirlineFlightNo
Southwest AirlinesWN4661
16:45
AirlineFlightNo
Southwest AirlinesWN1733
19:05
AirlineFlightNo
Southwest AirlinesWN4193
VIEW FLIGHTS
Thursday
06:50
AirlineFlightNo
Southwest AirlinesWN2570
08:10
AirlineFlightNo
Southwest AirlinesWN4729
12:00
AirlineFlightNo
Southwest AirlinesWN4661
12:20
AirlineFlightNo
VolarisY42709
FrontierF93853
13:15
AirlineFlightNo
Southwest AirlinesWN4730
14:15
AirlineFlightNo
Southwest AirlinesWN4968
17:20
AirlineFlightNo
Southwest AirlinesWN2574
19:05
AirlineFlightNo
Southwest AirlinesWN4193
20:25
AirlineFlightNo
Southwest AirlinesWN1057
VIEW FLIGHTS
Friday
06:55
AirlineFlightNo
Southwest AirlinesWN2570
08:10
AirlineFlightNo
Southwest AirlinesWN4729
11:50
AirlineFlightNo
Southwest AirlinesWN4661
14:15
AirlineFlightNo
Southwest AirlinesWN4968
14:26
AirlineFlightNo
VolarisY42709
FrontierF93853
17:20
AirlineFlightNo
Southwest AirlinesWN2574
19:05
AirlineFlightNo
Southwest AirlinesWN4193
20:25
AirlineFlightNo
Southwest AirlinesWN1057
VIEW FLIGHTS
Saturday
07:35
AirlineFlightNo
Southwest AirlinesWN2570
08:35
AirlineFlightNo
Southwest AirlinesWN4729
14:05
AirlineFlightNo
Southwest AirlinesWN4968
14:55
AirlineFlightNo
VolarisY42709
FrontierF93853
15:30
AirlineFlightNo
Southwest AirlinesWN1364
16:40
AirlineFlightNo
Southwest AirlinesWN823
17:50
AirlineFlightNo
Southwest AirlinesWN2574
21:30
AirlineFlightNo
Southwest AirlinesWN1057
VIEW FLIGHTS
Sunday
06:50
AirlineFlightNo
Southwest AirlinesWN2570
11:30
AirlineFlightNo
Southwest AirlinesWN4664
14:26
AirlineFlightNo
VolarisY42709
FrontierF93853
14:50
AirlineFlightNo
Southwest AirlinesWN4661
17:59
AirlineFlightNo
Southwest AirlinesWN4806
20:00
AirlineFlightNo
Southwest AirlinesWN4794
21:00
AirlineFlightNo
Southwest AirlinesWN4193
22:25
AirlineFlightNo
Southwest AirlinesWN1733
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
Jacksonville to Chicago Midway01,368 km (850 miles)2 Hours 25 Minutes
Ocala to Chicago Midway01,489 km (925 miles)2 Hours 34 Minutes
Punta Gorda Charlotte County to Chicago Midway01,734 km (1,078 miles)2 Hours 51 Minutes
Clearwater St Petersburg Clearwater to Chicago Midway01,610 km (1,000 miles)2 Hours 42 Minutes
Sarasota to Chicago Midway01,668 km (1,037 miles)2 Hours 46 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 £23.45 ($32 €26.98)
£23.45
$32 | €26.98
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 £50.57 ($69 €58.17)
£50.57
$69 | €58.17
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...