Orlando International to Chicago Midway Flights

If it is your first time travelling to Midway then check out the airliners Thrive, Volaris, Frontier and Southwest Airlines. These airliners all offer direct flights that depart from Orlando International, so you will find flying to Midway is quite easy. The flight time is approximately 2 Hours 41 Minutes.

The exact cost of the flight we vary quite significantly base on the dates you travel, the time of day you will depart and how long in advance you pre book the flights. The cheapest flights available will generally be mid week or late in the evening, so if you are on a budget then these are the flight times you should consider. Alternatively, you could book well in advance and you flight could be up to 50% cheaper, especially with budget airliners. The ticket prices for most airliners will increase the close you get the departure date, so as soon as you know the date you will travel you should book your flights.

When arriving at Midway don’t forget to set your watch to the local time!

For a full summary of all the airliners that fly from Orlando International to Midway, please see the table below.

AirlinerMoTuWeThFrSaSuFirst FlightLast Flight
Southwest Airlines777777708:1523:30
Frontier100211211:5222:36
Volaris100110111:5222:36
Thrive000100017:1017:10

Southwest Airlines offer the highest number of flights for this route with departures times between 08:15 and 23:30.

You can find the latest flight availability and prices from Southwest Airlines at www.southwest.com/?ref=southwestairlines.com. You can also book direct and get their latest discounts.

Flight times for Southwest Airlines are summarised in the table below. These time were correct at the time of writing, but please be aware that times may vary from time to time so please check their website for exact times and the dates you wish to fly.

DayFlying Time
Monday08:15, 09:45, 11:25, 14:35, 19:50, 21:00 and 23:30
Tuesday09:05, 11:30, 13:00, 14:50, 17:40, 20:20 and 23:10
Wednesday09:05, 11:30, 13:00, 14:50, 17:40, 20:20 and 23:10
Thursday08:15, 09:45, 11:25, 14:35, 19:50, 21:00 and 23:30
Friday08:15, 09:45, 11:25, 14:35, 19:50, 21:00 and 23:30
Saturday09:35, 11:35, 14:25, 16:30, 18:55, 20:10 and 22:25
Sunday09:20, 10:50, 12:00, 15:15, 17:25, 20:50 and 23:20

If you are flexible on the airport you depart from, then there are other airports that offer direct flights to Midway. You can see full details of these below.

RouteStopsDistanceFlying Time
Orlando to Grand Rapids Gerald R Ford01,651 km (1,026 miles)2 Hours 45 Minutes
Orlando to Milwaukee General Mitchell01,719 km (1,068 miles)2 Hours 50 Minutes
Orlando to Madison Dane County Regional01,787 km (1,110 miles)2 Hours 55 Minutes
Orlando to Chicago O'Hare01,620 km (1,007 miles)2 Hours 43 Minutes
Orlando to Chicago Pal Waukee01,624 km (1,009 miles)2 Hours 43 Minutes

Please remember to leave plenty of time to get though customers when you are departing form the airports. Flights regulations are getting very strict these days so getting through customs can take in excess of 1 hour in some cases.

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