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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
$567
Southwest Airlines• nonstop • 3h 55mJun 29 – Jul 06
The cheapest round trip flight from San Antonio International to Chicago Midway International is currently $567
Cheapest One way Flight
$861
Southwest Airlines• 4 stops• 40h 35mJun 29
The cheapest one way flight from Philip S. W. Goldson International to Chicago Midway International is currently $861
Cheapest Direct Flight
$363
Southwest Airlines• nonstop• 4h 5mJul 01
The cheapest nonstop flight from Orlando International to Chicago Midway International is currently $363
Fastest Flight
3h 55m
The fastest nonstop flight from San Antonio International to Chicago Midway International takes 3h 55m
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 29 - Jul 06, Economy
San Antonio → Chicago
3h 55m
3:20 PM - 5:55 PM • nonstop
San Antonio → Chicago
11h 55m
12:20 PM - 7:35 PM • 1 stop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
10h 50m
12:25 PM - 7:15 PM • 1 stop
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
8h 40m
1:50 PM - 7:10 PM • 1 stop
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
10h 55m
5:45 PM - 12:40 AM • 1 stop
San Antonio → Chicago
4h
10:35 AM - 1:15 PM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
10h 15m
12:50 PM - 7:05 PM • 1 stop
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
Southwest 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 29 - Jul 06, Economy
San Antonio → Chicago
3h 55m
3:20 PM - 5:55 PM • nonstop
San Antonio → Chicago
11h 55m
12:20 PM - 7:35 PM • 1 stop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
10h 50m
12:25 PM - 7:15 PM • 1 stop
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
8h 40m
1:50 PM - 7:10 PM • 1 stop
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
10h 55m
5:45 PM - 12:40 AM • 1 stop
San Antonio → Chicago
4h
10:35 AM - 1:15 PM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
10h 15m
12:50 PM - 7:05 PM • 1 stop
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
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.
Jul 01 - Jul 07, Economy
Orlando → Chicago
4h 5m
1:30 PM - 3:15 PM • nonstop
Orlando → Chicago
4h
12:00 PM - 3:40 PM • nonstop
Southwest Airlines
Jul 01 - Jul 07, Economy
Orlando → Chicago
4h 10m
2:30 PM - 4:20 PM • nonstop
Orlando → Chicago
4h 10m
5:30 PM - 9:20 PM • nonstop
Southwest Airlines
Jul 01 - Jul 07, Economy
Orlando → Chicago
4h 10m
8:10 PM - 10:00 PM • nonstop
Orlando → Chicago
3h 50m
5:10 AM - 8:40 AM • nonstop
Southwest Airlines
Jul 01 - Jul 07, Economy
Orlando → Chicago
4h 10m
7:10 AM - 9:00 AM • nonstop
Orlando → Chicago
3h 55m
7:55 AM - 11:30 AM • nonstop
Southwest Airlines
Jun 29 - Jul 06, Economy
San Antonio → Chicago
3h 55m
3:20 PM - 5:55 PM • nonstop
San Antonio → Chicago
4h 5m
9:25 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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