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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
$357
Southwest Airlines• 1 stop • 15h 5mJan 03 – Jan 06
The cheapest round trip flight from San Antonio International to Chicago Midway International is currently $357
Cheapest One way Flight
$147
Frontier Airlines• 1 stop• 17h 37mDec 29
The cheapest one way flight from Orlando International to Chicago Midway International is currently $147
Cheapest Direct Flight
$274
American Airlines• nonstop• 5h 10mDec 31
The cheapest nonstop flight from Orlando International to Chicago Midway International is currently $274
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.
Jan 03 - Jan 06, Economy
San Antonio → Chicago
15h 5m
12:50 PM - 9:55 PM • 1 stop
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 AM • nonstop
Southwest Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
13h 40m
1:30 PM - 9:50 PM • 2 stops
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 AM • nonstop
Southwest Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
14h 5m
12:45 PM - 9:30 PM • 2 stops
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 AM • nonstop
Southwest Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
15h
12:50 PM - 9:50 PM • 2 stops
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 AM • nonstop
Southwest Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
6h 40m
1:30 PM - 5:30 PM • 1 stop
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 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.
Dec 31 - Jan 09, Economy
Orlando → Chicago
8h 21m
2:59 PM - 10:07 PM • 1 stop
Orlando → Chicago
6h 58m
5:32 PM - 11:59 PM • 1 stop
Spirit Airlines
Dec 31 - Jan 09, Economy
Orlando → Chicago
8h 21m
2:59 PM - 10:07 PM • 1 stop
Orlando → Chicago
4h 7m
12:44 PM - 4:31 PM • nonstop
Spirit Airlines
Dec 31 - Jan 09, Economy
Orlando → Chicago
6h 50m
3:03 PM - 7:22 PM • 1 stop
Orlando → Chicago
4h 9m
2:50 PM - 6:39 PM • nonstop
American Airlines
Dec 31 - Jan 09, Economy
Orlando → Chicago
7h 4m
8:47 AM - 6:33 PM • 1 stop
Orlando → Chicago
4h 7m
4:31 PM - 8:18 PM • nonstop
Frontier Airlines
Dec 31 - Jan 09, Economy
Orlando → Chicago
8h 30m
2:55 PM - 7:05 PM • 1 stop
Orlando → Chicago
6h 55m
8:10 AM - 1:25 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.
Dec 31 - Jan 09, Economy
Orlando → Chicago
5h 10m
5:35 PM - 7:45 PM • nonstop
Orlando → Chicago
4h 12m
6:00 PM - 9:52 PM • nonstop
American Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
3h 55m
6:05 AM - 8:40 AM • nonstop
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 AM • nonstop
Southwest Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
3h 55m
5:15 PM - 7:50 PM • nonstop
San Antonio → Chicago
5h 5m
8:20 AM - 11:25 AM • nonstop
Southwest Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
4h 19m
6:30 AM - 9:29 AM • nonstop
San Antonio → Chicago
5h 7m
7:30 PM - 10:37 PM • nonstop
Alaska Airlines
Jan 03 - Jan 06, Economy
San Antonio → Chicago
4h 13m
6:32 PM - 9:25 PM • nonstop
San Antonio → Chicago
5h 7m
7:30 PM - 10:37 PM • nonstop
Alaska 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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