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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
$373
Southwest Airlines• 1 stop • 10h 10mApr 09 – Apr 13
The cheapest round trip flight from Portland International to Chicago Midway International is currently $373
Cheapest One way Flight
$143
Southwest Airlines• 1 stop• 20h 25mFeb 14
The cheapest one way flight from Orlando International to Chicago Midway International is currently $143
Cheapest Direct Flight
$167
Southwest Airlines• nonstop• 4h 5mMar 27
The cheapest nonstop flight from Logan International to Chicago Midway International is currently $167
Fastest Flight
1h 55m
The fastest nonstop flight from Louisville International Standiford Field to Chicago Midway International takes 1h 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.
Apr 09 - Apr 13, Economy
Portland → Chicago
10h 10m
6:10 AM - 2:20 PM • 1 stop
Portland → Chicago
7h
9:50 PM - 12:10 AM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
15h 55m
6:10 AM - 6:05 PM • 1 stop
Portland → Chicago
7h
9:50 PM - 12:10 AM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
15h 10m
8:35 AM - 7:45 PM • 1 stop
Portland → Chicago
7h
10:15 AM - 12:35 PM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
15h 30m
6:25 AM - 5:55 PM • 1 stop
Portland → Chicago
7h
10:15 AM - 12:35 PM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
12h 30m
6:25 AM - 4:15 PM • 1 stop
Portland → Chicago
7h
9:50 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.
Feb 13 - Feb 15, Economy
Louisville → Chicago
20h 55m
7:00 AM - 6:55 PM • 1 stop
Louisville → Chicago
1h 55m
9:55 AM - 12:10 PM • nonstop
Southwest Airlines
Feb 13 - Feb 15, Economy
Louisville → Chicago
15h
7:00 AM - 3:00 PM • 1 stop
Louisville → Chicago
1h 55m
8:45 PM - 11:00 PM • nonstop
Southwest Airlines
Feb 13 - Feb 15, Economy
Louisville → Chicago
20h 25m
7:00 AM - 6:25 PM • 2 stops
Louisville → Chicago
1h 55m
8:45 PM - 11:00 PM • nonstop
Southwest Airlines
Feb 13 - Feb 15, Economy
Louisville → Chicago
2h 5m
6:30 AM - 6:55 AM • nonstop
Louisville → Chicago
13h 30m
8:00 AM - 5:10 PM • 2 stops
Southwest Airlines
Feb 13 - Feb 15, Economy
Louisville → Chicago
20h 55m
7:00 AM - 6:55 PM • 1 stop
Louisville → Chicago
10h 10m
2:15 PM - 9:25 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.
Mar 27 - Mar 29, Economy
Boston → Chicago
4h 5m
3:10 PM - 4:55 PM • nonstop
Boston → Chicago
3h 35m
7:30 PM - 10:45 PM • nonstop
Southwest Airlines
Feb 13 - Feb 15, Economy
Louisville → Chicago
2h 5m
6:30 AM - 6:55 AM • nonstop
Louisville → Chicago
1h 55m
9:55 AM - 12:10 PM • nonstop
Southwest Airlines
Feb 13 - Feb 15, Economy
Louisville → Chicago
1h 55m
8:40 PM - 8:55 PM • nonstop
Louisville → Chicago
1h 55m
8:45 PM - 11:00 PM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
5h 55m
5:10 AM - 11:05 AM • nonstop
Portland → Chicago
7h
9:50 PM - 12:10 AM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
5h 55m
11:55 PM - 5:50 AM • nonstop
Portland → Chicago
7h
9:50 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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