Orlando Airport (MCO) Flights to Chicago Airport (MDW)

We've found the cheapest flights to Chicago

Returns from £72.92

One-way from £36.09

Flights are available to Orlando International from Midway with a choice of 4 airliners, Executive Fliteways, Volaris, Frontier and Southwest Airlines. The journey time flying from Orlando International to Midway United States is around 2 Hours 41 Minutes. With the distance covered being 1,595 Km (991 Miles). The airport code for Orlando International is MCO and for Midway it is MDW.

The cost of the air travel varies depending on what day you travel and the time of day. Midway United States flights may be normally booked months in advance and this may be the best option if you intend to get the best prices from Orlando International. 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.

The table below displays the numbers of daily flights from Orlando International (MCO) to Midway (MDW) and the relevant airlines that fly.

Flights Chart
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines888888706:2022:50VIEW FLIGHTS
Volaris100111118:2218:22VIEW FLIGHTS
Frontier100111118:2218:22VIEW FLIGHTS
Executive Fliteways010000019:3019:30VIEW FLIGHTS

The most direct flights offered from Orlando International to Midway United States are by Southwest Airlines with around 55 flights a week. These operate from 06:20 with the latest flight being at 22:50. The most popular flight no is WN1719, WN1788, WN2549 and WN255.

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 AirlinesWN3716
07:55
AirlineFlightNo
Southwest AirlinesWN1719
09:20
AirlineFlightNo
Southwest AirlinesWN3255
11:30
AirlineFlightNo
Southwest AirlinesWN2549
15:30
AirlineFlightNo
Southwest AirlinesWN1788
17:45
AirlineFlightNo
Southwest AirlinesWN3724
18:22
AirlineFlightNo
VolarisY42472
FrontierF93853
20:20
AirlineFlightNo
Southwest AirlinesWN3726
21:50
AirlineFlightNo
Southwest AirlinesWN2634
VIEW FLIGHTS
Tuesday
06:20
AirlineFlightNo
Southwest AirlinesWN3724
07:45
AirlineFlightNo
Southwest AirlinesWN3716
10:30
AirlineFlightNo
Southwest AirlinesWN1719
14:00
AirlineFlightNo
Southwest AirlinesWN3643
15:20
AirlineFlightNo
Southwest AirlinesWN4028
16:15
AirlineFlightNo
Southwest AirlinesWN3255
17:25
AirlineFlightNo
Southwest AirlinesWN2634
19:30
AirlineFlightNo
Executive FlitewaysXFL251
21:55
AirlineFlightNo
Southwest AirlinesWN3726
VIEW FLIGHTS
Wednesday
06:20
AirlineFlightNo
Southwest AirlinesWN3724
07:45
AirlineFlightNo
Southwest AirlinesWN3716
10:30
AirlineFlightNo
Southwest AirlinesWN1719
14:00
AirlineFlightNo
Southwest AirlinesWN3643
15:20
AirlineFlightNo
Southwest AirlinesWN4028
16:15
AirlineFlightNo
Southwest AirlinesWN3255
17:25
AirlineFlightNo
Southwest AirlinesWN2634
21:55
AirlineFlightNo
Southwest AirlinesWN3726
VIEW FLIGHTS
Thursday
06:35
AirlineFlightNo
Southwest AirlinesWN3716
07:55
AirlineFlightNo
Southwest AirlinesWN1719
09:20
AirlineFlightNo
Southwest AirlinesWN3255
11:30
AirlineFlightNo
Southwest AirlinesWN2549
15:30
AirlineFlightNo
Southwest AirlinesWN1788
17:45
AirlineFlightNo
Southwest AirlinesWN3724
18:22
AirlineFlightNo
VolarisY42472
FrontierF93853
20:20
AirlineFlightNo
Southwest AirlinesWN3726
21:50
AirlineFlightNo
Southwest AirlinesWN2634
VIEW FLIGHTS
Friday
06:35
AirlineFlightNo
Southwest AirlinesWN3716
07:55
AirlineFlightNo
Southwest AirlinesWN1719
09:20
AirlineFlightNo
Southwest AirlinesWN3255
11:30
AirlineFlightNo
Southwest AirlinesWN2549
15:30
AirlineFlightNo
Southwest AirlinesWN1788
17:45
AirlineFlightNo
Southwest AirlinesWN3724
18:22
AirlineFlightNo
VolarisY42472
FrontierF93853
20:20
AirlineFlightNo
Southwest AirlinesWN3726
21:50
AirlineFlightNo
Southwest AirlinesWN2634
VIEW FLIGHTS
Saturday
06:40
AirlineFlightNo
Southwest AirlinesWN3716
09:15
AirlineFlightNo
Southwest AirlinesWN3255
10:20
AirlineFlightNo
Southwest AirlinesWN2549
13:05
AirlineFlightNo
Southwest AirlinesWN1164
15:55
AirlineFlightNo
Southwest AirlinesWN1788
17:00
AirlineFlightNo
Southwest AirlinesWN3724
18:22
AirlineFlightNo
VolarisY42472
FrontierF93853
20:10
AirlineFlightNo
Southwest AirlinesWN3726
21:00
AirlineFlightNo
Southwest AirlinesWN2634
VIEW FLIGHTS
Sunday
06:25
AirlineFlightNo
Southwest AirlinesWN3716
08:05
AirlineFlightNo
Southwest AirlinesWN1719
10:55
AirlineFlightNo
Southwest AirlinesWN2549
14:55
AirlineFlightNo
Southwest AirlinesWN1788
18:20
AirlineFlightNo
Southwest AirlinesWN3724
18:22
AirlineFlightNo
VolarisY42472
FrontierF93853
20:00
AirlineFlightNo
Southwest AirlinesWN255
22:50
AirlineFlightNo
Southwest AirlinesWN2634
VIEW FLIGHTS

Instead of flying directly from Orlando International and arrive at Midway, you may arrive Midway by another airport. Please see chart below for a list of these.

Alternative Direct Routes
RouteStopsDistanceFlying Time
Kissimmee to Chicago Midway01,607 km (998 miles)2 Hours 42 Minutes
Jacksonville to Chicago Midway01,368 km (850 miles)2 Hours 25 Minutes
Orlando Executive to Chicago Midway01,583 km (984 miles)2 Hours 40 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
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

Before departing customs Orlando International make sure that you do not exceed baggage allowances as excess charges may be considerable.

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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 £36.09 ($49 €42.33)
£36.09
$49 | €42.33
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 £72.92 ($99 €85.53)
£72.92
$99 | €85.53
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.

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

Who flies from Orlando to Chicago?
The following airlines fly from Orlando (MCO) to Chicago (MDW): Executive Fliteways, 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

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