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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
$86
Southwest Airlines• 1 stop • 8h 40mJun 16 – Jun 22
The cheapest round trip flight from Orlando International to Chicago Midway International is currently $86
Cheapest One way Flight
$132
Southwest Airlines• 1 stop• 10h 50mJun 21
The cheapest one way flight from Phoenix Sky Harbor International to Chicago Midway International is currently $132
Cheapest Direct Flight
$195
Southwest Airlines• nonstop• 4h 15mJun 16
The cheapest nonstop flight from Orlando International to Chicago Midway International is currently $195
Fastest Flight
4h 5m
The fastest nonstop flight from Orlando International to Chicago Midway International takes 4h 5m
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.
Jun 16 - Jun 22, Economy
Orlando → Chicago
8h 40m
12:30 PM - 4:50 PM • 1 stop
Orlando → Chicago
6h 50m
4:40 PM - 9:50 PM • 1 stop
Southwest Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
5h 18m
9:01 PM - 11:19 PM • nonstop
Orlando → Chicago
4h 13m
5:07 PM - 9:00 PM • nonstop
Frontier Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
5h 16m
4:13 PM - 6:29 PM • nonstop
Orlando → Chicago
4h 11m
6:45 PM - 10:36 PM • nonstop
American Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
25h 46m
7:25 AM - 10:11 PM • 2 stops
Orlando → Chicago
10h 34m
4:10 PM - 11:44 PM • 1 stop
Frontier Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
41h 44m
10:07 PM - 10:11 PM • 2 stops
Orlando → Chicago
82h 9m
9:23 PM - 11:52 PM • 2 stops
Frontier 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.
Jun 16 - Jun 22, Economy
Orlando → Chicago
8h 40m
12:30 PM - 4:50 PM • 1 stop
Orlando → Chicago
6h 50m
4:40 PM - 9:50 PM • 1 stop
Southwest Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
5h 18m
9:01 PM - 11:19 PM • nonstop
Orlando → Chicago
4h 13m
5:07 PM - 9:00 PM • nonstop
Frontier Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
5h 16m
4:13 PM - 6:29 PM • nonstop
Orlando → Chicago
4h 11m
6:45 PM - 10:36 PM • nonstop
American Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
25h 46m
7:25 AM - 10:11 PM • 2 stops
Orlando → Chicago
10h 34m
4:10 PM - 11:44 PM • 1 stop
Frontier Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
41h 44m
10:07 PM - 10:11 PM • 2 stops
Orlando → Chicago
82h 9m
9:23 PM - 11:52 PM • 2 stops
Frontier 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.
Jun 16 - Jun 22, Economy
Orlando → Chicago
4h 15m
4:20 PM - 6:15 PM • nonstop
Orlando → Chicago
4h 5m
5:10 PM - 8:55 PM • nonstop
Southwest Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
5h 18m
9:01 PM - 11:19 PM • nonstop
Orlando → Chicago
4h 13m
5:07 PM - 9:00 PM • nonstop
Frontier Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
5h 16m
4:13 PM - 6:29 PM • nonstop
Orlando → Chicago
4h 11m
6:45 PM - 10:36 PM • nonstop
American Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
4h 10m
2:30 PM - 4:20 PM • nonstop
Orlando → Chicago
4h 5m
5:10 PM - 8:55 PM • nonstop
Southwest Airlines
Jun 16 - Jun 22, Economy
Orlando → Chicago
4h 10m
8:00 AM - 9:50 AM • nonstop
Orlando → Chicago
3h 55m
8:55 PM - 12:30 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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