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Good to Know: Flights to MDW
Useful information for finding cheap flights to Chicago Midway International and booking your next trip
Cheapest Round Trip Flight
$428
Frontier Airlines• 1 stop • 15h 32mMay 25 – May 28
The cheapest round trip flight from Orlando International to Chicago Midway International is currently $428
Cheapest One way Flight
$445
Southwest Airlines• 1 stop• 23h 55mMay 19
The cheapest one way flight from Dallas Love Field to Chicago Midway International is currently $445
Cheapest Direct Flight
$450
Southwest Airlines• nonstop• 5h 25mMay 21
The cheapest nonstop flight from Phoenix Sky Harbor International to Chicago Midway International is currently $450
Fastest Flight
4h 10m
The fastest nonstop flight from Orlando International to Chicago Midway International takes 4h 10m
Best Flight Deals to Chicago
Identify the most efficient round-trip flights to Chicago. We present options balancing cost and convenience for your return journey.
May 25 - May 28, Economy
Orlando → Chicago
15h 32m
5:40 AM - 2:12 PM • 1 stop
Orlando → Chicago
4h 15m
6:45 PM - 10:40 PM • nonstop
Frontier Airlines
May 21 - May 24, Economy
Phoenix → Chicago
5h 25m
1:25 PM - 6:50 PM • nonstop
Phoenix → Chicago
9h 15m
1:15 PM - 5:10 PM • 1 stop
Southwest Airlines
May 21 - May 24, Economy
Phoenix → Chicago
9h 5m
9:55 PM - 5:40 AM • 1 stop
Phoenix → Chicago
8h 20m
11:15 AM - 2:15 PM • 1 stop
Southwest Airlines
May 21 - May 24, Economy
Phoenix → Chicago
8h 50m
9:55 PM - 5:25 AM • 1 stop
Phoenix → Chicago
8h 20m
11:15 AM - 2:15 PM • 1 stop
Southwest Airlines
May 25 - May 28, Economy
Orlando → Chicago
12h 6m
5:30 AM - 11:56 AM • 1 stop
Orlando → Chicago
7h 1m
12:53 PM - 6:14 PM • 1 stop
Delta Airlines
For travel requiring no set return, access available one-way flights to Chicago (MDW). These options support extended stays or open-ended plans.
Need to travel to Chicago soon? View current last-minute flight options to MDW for spontaneous or pressing plans.
May 14 - May 16, Economy
Orlando → Chicago
9h 12m
5:10 PM - 10:02 PM • 1 stop
Orlando → Chicago
10h 33m
11:59 AM - 7:32 PM • 1 stop
Frontier Airlines
May 14 - May 16, Economy
Orlando → Chicago
4h 10m
10:10 AM - 12:00 PM • nonstop
Orlando → Chicago
3h 55m
11:25 AM - 3:00 PM • nonstop
Southwest Airlines
May 14 - May 16, Economy
Orlando → Chicago
4h 15m
7:20 AM - 9:15 AM • nonstop
Orlando → Chicago
4h
5:25 PM - 9:05 PM • nonstop
Southwest Airlines
May 14 - May 16, Economy
Orlando → Chicago
7h
2:20 PM - 5:40 PM • 1 stop
Orlando → Chicago
3h 50m
5:15 AM - 8:45 AM • nonstop
Southwest Airlines
May 14 - May 16, Economy
Orlando → Chicago
4h 15m
7:20 AM - 9:15 AM • nonstop
Orlando → Chicago
5h 50m
7:40 AM - 12:30 PM • 1 stop
Southwest Airlines
Maximize your time in Chicago, not in transit. Discover non-stop direct flights to MDW for the quickest, most straightforward journey to the Strip.
May 21 - May 24, Economy
Phoenix → Chicago
5h 25m
8:20 AM - 1:45 PM • nonstop
Phoenix → Chicago
5h 50m
6:15 AM - 8:05 AM • nonstop
Southwest Airlines
May 21 - May 24, Economy
Phoenix → Chicago
5h 15m
7:30 AM - 12:45 PM • nonstop
Phoenix → Chicago
5h 50m
6:15 AM - 8:05 AM • nonstop
Southwest Airlines
May 25 - May 28, Economy
Orlando → Chicago
5h 10m
7:35 AM - 9:45 AM • nonstop
Orlando → Chicago
4h 5m
7:35 PM - 11:20 PM • nonstop
Southwest Airlines
May 25 - May 28, Economy
Orlando → Chicago
4h 10m
11:40 AM - 1:30 PM • nonstop
Orlando → Chicago
3h 55m
7:40 AM - 11:15 AM • nonstop
Southwest Airlines
May 25 - May 28, Economy
Orlando → Chicago
4h 15m
5:05 PM - 7:00 PM • nonstop
Orlando → Chicago
3h 55m
8:35 PM - 12:10 AM • nonstop
Southwest Airlines
Destination Airport Information
| IATA Code | MDW |
| Name | Chicago Midway International |
| City | Chicago |
| Country | US |
| Latitude | 41.7859992980957 |
| Longitude | -87.75240325927734 |
Popular Airlines
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