- Cheapest roundtrip flight
- from€210
- Fastest flight
- non-stop flights
- 36x / week
- Flight distance
- 1,597 km
- Time difference
- Most popular airlines
- Southwest Airlines
- Southwest Airlines
Flight schedule from Orlando (MCO) to Chicago Midway (MDW)
Select a travel date in the flight schedule for the route from Orlando (MCO) to Chicago Midway (MDW) and compare affordable flight deals.
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Matching outbound flightsMCO–MDW · 51 of 51
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- Sep 27 – Oct 3, 2026
- October 4 – 10, 2026
- October 11 – 17, 2026
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Tips and tricks to help you find cheap flights from Orlando to Chicago Midway
Favorite airline: Frontier Airlines
80 % of flights from Orlando to Chicago Midway are booked with Frontier Airlines.
Frontier Airlines
80 %
Delta
20 %
Important flight information
Frequently Asked Questions (FAQ)
How long is the flight from Orlando to Chicago Midway?
A nonstop flight from Orlando to Chicago Midway typically takes around 2 hours 55 minutes. This makes the nonstop service the fastest and most convenient way to travel between Orlando and Chicago Midway. It is worth checking flight times when searching, as they can vary by airline and travel date.
Are there nonstop flights from Orlando to Chicago Midway?
Yes, there are nonstop flights from Orlando to Chicago Midway, averaging around 5 to 6 flights per day, operated by, among others, Southwest. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
Which airlines fly from Orlando to Chicago Midway?
Direct flights from Orlando to Chicago Midway are operated by, among others, Southwest. These flights take you to Chicago Midway nonstop, making them especially practical for short trips or weekend getaways. It is still worth comparing departure times and airline policies, as baggage rules and fees can vary.
On which days are there nonstop flights from Orlando to Chicago Midway?
Nonstop flights from Orlando to Chicago Midway operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
How many flights are there per day from Orlando to Chicago Midway?
From Orlando to Chicago Midway, there are on average around 5 to 6 flights per day. This usually means you have a good choice of departure times. If you are flexible, you can easily compare times, prices, and airlines.
How many flights per week are there from Orlando to Chicago Midway?
From Orlando to Chicago Midway, there are around 36 to 37 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
When does the first flight from Orlando to Chicago Midway depart?
The earliest nonstop flight from Orlando to Chicago Midway usually departs at 6:20 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in Chicago Midway.
When does the last flight from Orlando to Chicago Midway depart?
The last nonstop flight from Orlando to Chicago Midway usually departs at 10:50 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.