Lowest Prices
Find the lowest MDW airfares by comparing hundreds of airlines and agencies.
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
$158
Southwest Airlines• 1 stop • 7h 5mMay 21 – May 23
The cheapest round trip flight from William P Hobby to Chicago Midway International is currently $158
Cheapest One way Flight
$240
Southwest Airlines• 1 stop• 5h 55mMay 07
The cheapest one way flight from Dallas Love Field to Chicago Midway International is currently $240
Cheapest Direct Flight
$198
Southwest Airlines• nonstop• 3h 45mMay 09
The cheapest nonstop flight from William P Hobby to Chicago Midway International is currently $198
Fastest Flight
3h 45m
The fastest nonstop flight from William P Hobby to Chicago Midway International takes 3h 45m
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.
May 21 - May 23, Economy
Houston → Chicago
7h 5m
7:35 AM - 12:00 PM • 1 stop
Houston → Chicago
7h
12:55 PM - 5:15 PM • 1 stop
Southwest Airlines
May 21 - May 23, Economy
Houston → Chicago
16h 50m
10:20 AM - 8:30 PM • 1 stop
Houston → Chicago
4h
3:00 PM - 5:40 PM • nonstop
Southwest Airlines
May 21 - May 23, Economy
Houston → Chicago
17h 15m
9:55 PM - 8:30 AM • 1 stop
Houston → Chicago
4h
3:00 PM - 5:40 PM • nonstop
Southwest Airlines
May 21 - May 23, Economy
Houston → Chicago
7h 30m
7:00 AM - 11:50 AM • 1 stop
Houston → Chicago
7h
12:55 PM - 5:15 PM • 1 stop
Southwest Airlines
May 24 - May 24, Economy
Houston → Chicago
11h 55m
9:30 AM - 4:45 PM • 1 stop
Houston → Chicago
16h 50m
9:10 PM - 7:20 AM • 1 stop
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.
Maximize your time in Chicago, not in transit. Discover non-stop direct flights to MDW for the quickest, most straightforward journey to the Strip.
May 09 - May 09, Economy
Houston → Chicago
3h 45m
7:00 AM - 9:25 AM • nonstop
Houston → Chicago
4h
3:00 PM - 5:40 PM • nonstop
Southwest Airlines
May 21 - May 23, Economy
Houston → Chicago
3h 45m
7:30 PM - 9:55 PM • nonstop
Houston → Chicago
4h 5m
6:05 PM - 8:50 PM • nonstop
Southwest Airlines
May 22 - May 24, Economy
Houston → Chicago
3h 45m
8:00 AM - 10:25 AM • nonstop
Houston → Chicago
4h
5:15 PM - 7:55 PM • nonstop
Southwest Airlines
May 22 - May 24, Economy
Houston → Chicago
3h 50m
12:55 PM - 3:25 PM • nonstop
Houston → Chicago
4h
11:10 AM - 1:50 PM • nonstop
Southwest Airlines
May 22 - May 24, Economy
Houston → Chicago
3h 45m
5:10 AM - 7:35 AM • nonstop
Houston → Chicago
4h
9:20 AM - 12:00 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
More Flight Options to Chicago, MDW
Why Bargainspricer for Flights to MDW
New Deals Everyday
Never miss a deal on MDW flights—we update prices daily to bring you the best airfares.
Best Travel Options
Compare hundreds of MDW flights and find the best deals without any added service charges.