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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 • 16h 45mApr 09 – Apr 13
The cheapest round trip flight from Portland International to Chicago Midway International is currently $373
Cheapest One way Flight
$97
Southwest Airlines• 2 stops• 13h 20mMar 22
The cheapest one way flight from McCarran International to Chicago Midway International is currently $97
Cheapest Direct Flight
$373
Southwest Airlines• nonstop• 5h 55mApr 09
The cheapest nonstop flight from Portland International to Chicago Midway International is currently $373
Fastest Flight
2h 15m
The fastest nonstop flight from Pittsburgh International to Chicago Midway International takes 2h 15m
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
16h 45m
4:55 PM - 5:00 AM • 1 stop
Portland → Chicago
7h
9:50 PM - 12:10 AM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
10h 55m
3:00 PM - 11:55 PM • 1 stop
Portland → Chicago
7h
10:15 AM - 12:35 PM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
10h 50m
2:50 PM - 11:40 PM • 1 stop
Portland → Chicago
7h
9:50 PM - 12:10 AM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
13h 55m
10:40 AM - 9:15 PM • 1 stop
Portland → Chicago
7h
9:50 PM - 12:10 AM • nonstop
Southwest Airlines
Apr 09 - Apr 13, Economy
Portland → Chicago
11h 40m
1:10 PM - 10:10 PM • 1 stop
Portland → Chicago
7h
10:15 AM - 12:35 PM • 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 07 - Feb 07, Economy
Pittsburgh → Chicago
2h 30m
6:35 AM - 7:25 AM • nonstop
Pittsburgh → Chicago
2h 5m
9:45 AM - 12:10 PM • nonstop
Southwest Airlines
Feb 07 - Feb 07, Economy
Pittsburgh → Chicago
8h 53m
6:32 AM - 11:05 AM • 1 stop
Pittsburgh → Chicago
7h 12m
6:03 PM - 11:35 PM • 1 stop
Delta Airlines
Feb 07 - Feb 07, Economy
Pittsburgh → Chicago
8h 30m
7:15 AM - 11:25 AM • 1 stop
Pittsburgh → Chicago
2h
5:30 PM - 7:50 PM • nonstop
Southwest Airlines
Feb 07 - Feb 07, Economy
Pittsburgh → Chicago
8h 30m
7:15 AM - 11:25 AM • 1 stop
Pittsburgh → Chicago
25h 30m
7:40 PM - 12:10 PM • 2 stops
Southwest Airlines
Feb 07 - Feb 07, Economy
Pittsburgh → Chicago
12h 5m
7:15 AM - 1:40 PM • 2 stops
Pittsburgh → Chicago
34h 5m
7:40 PM - 5:25 PM • 2 stops
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.
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
Feb 06 - Feb 06, Economy
Atlanta → Chicago
2h 35m
6:45 PM - 7:40 PM • nonstop
Atlanta → Chicago
2h 30m
6:00 PM - 8:50 PM • nonstop
Southwest Airlines
Feb 06 - Feb 06, Economy
Atlanta → Chicago
2h 31m
9:31 PM - 10:22 PM • nonstop
Atlanta → Chicago
3h 37m
6:14 PM - 9:31 PM • nonstop
Delta Airlines
Feb 07 - Feb 07, Economy
Pittsburgh → Chicago
2h 15m
6:00 PM - 6:35 PM • nonstop
Pittsburgh → Chicago
2h
5:30 PM - 7:50 PM • 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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