
Round-trip from | $205 (Southwest) |
|---|---|
One-way from | $103 (Southwest) |
Popular in | January |
Cheapest in | October |
Average price | $322 |
Fly from
Fly to
Route
Depart
Return
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Sat 10/17
11:22 am-6:05 pm
1 stop6h 43m
Chicago Midway
Mon 10/19
5:15 pm-11:57 pm
1 stop6h 42m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 8/24
6:00 am-11:51 am
1 stop5h 51m
Chicago Midway
Wed 8/26
1:25 pm-10:05 pm
2 stops8h 40m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 8/4
4:37 pm-10:36 pm
1 stop5h 59m
Chicago Midway
Tue 8/11
1:25 pm-11:52 pm
2 stops10h 27m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 9/14
6:10 am-1:20 pm
1 stop7h 10m
Chicago Midway
Wed 9/16
9:29 am-5:39 pm
2 stops8h 10m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 8/6
3:05 pm-7:50 pm
1 stop4h 45m
Chicago Midway
Mon 8/10
5:25 am-7:50 am
Nonstop2h 25m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 8/12
10:50 am-6:33 pm
2 stops7h 43m
Chicago Midway
Wed 8/19
9:24 am-10:05 pm
2 stops12h 41m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 8/26
11:25 am-4:55 pm
2 stops5h 30m
Chicago Midway
Thu 8/27
10:05 am-1:55 pm
1 stop3h 50m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 8/27
5:20 am-12:39 pm
1 stop7h 19m
Chicago Midway
Tue 9/1
9:24 am-8:08 pm
2 stops10h 44m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 8/1
8:45 pm-11:15 pm
Nonstop2h 30m
Chicago Midway
Tue 8/4
8:25 pm-10:50 pm
Nonstop2h 25m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 8/4
8:50 pm-11:10 pm
Nonstop2h 20m
Chicago Midway
Wed 8/5
2:05 pm-4:35 pm
Nonstop2h 30m
Currently, October is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $56). Flying from Houston to Chicago Midway Airport in May is currently the most expensive (average of $188). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike at noon, when flights are generally more expensive, you can save up to 17% on flights from Houston to Chicago Midway Airport by exploring options for tickets in the evening.
About 21% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 119 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 20% of flights being delayed.
The price you pay for your flight from Houston to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Travelers seeking maximum savings on their Houston to Chicago Midway Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Overall
Comfort
Entertainment
Food
Boarding
Crew
Reviews
Reza,Jun 2026
TPA - MDW
Overall
Comfort
Entertainment
Food
Boarding
Crew
Reviews
Reza,Jun 2026
TPA - MDW
Overall
Comfort
Entertainment
Food
Boarding
Crew
Reviews
Reza,Jun 2026
TPA - MDW
Overall
Comfort
Entertainment
Food
Boarding
Crew
Reviews
Reza,Jun 2026
TPA - MDW
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$362 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$331 | FlexibilityNo cancel fee | On-timeN/A |