Frontier offers extra comfort seats with 32” separation for added legroom on short flights.
Early morning flights have a better chance of on-time departure, avoiding carry-over delays.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $83 (Orbitz) |
One-way from | $48 (Super.com) |
Popular in | February |
Cheapest in | January |
Average price | $116 |
Good round-trip deal | $150 or less |
Good one-way deal | $100 or less |
Fly from
Fly to
Route
Depart
Return
Price
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 2/23
10:30 am-1:08 pm
Nonstop2h 38m
Chicago Midway
Wed 2/25
7:00 am-5:12 pm
1 stop10h 12m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 3/9
1:43 pm-4:13 pm
Nonstop2h 30m
Chicago Midway
Mon 3/16
10:00 am-12:58 pm
Nonstop2h 58m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Wed 2/18
8:30 am-11:16 am
Nonstop2h 46m
Chicago O'Hare Intl
Sat 2/21
8:53 am-12:00 pm
Nonstop3h 07m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Wed 2/18
7:59 pm-2:26 pm
1 stop18h 27m
Chicago Midway
Sat 2/21
6:00 am-4:52 pm
1 stop10h 52m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 3/9
1:43 pm-4:13 pm
Nonstop2h 30m
Chicago Midway
Sat 3/14
6:00 am-5:18 pm
1 stop11h 18m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Sat 2/7
5:30 am-10:44 am
1 stop5h 14m
Chicago O'Hare Intl
Sat 2/7
2:59 pm-8:09 pm
1 stop5h 10m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Sat 2/14
2:23 pm-7:19 pm
1 stop4h 56m
Chicago O'Hare Intl
Mon 2/16
10:35 am-6:26 pm
1 stop7h 51m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Thu 3/12
6:54 pm-11:59 pm
1 stop5h 05m
Chicago O'Hare Intl
Mon 3/16
5:40 pm-10:59 pm
1 stop5h 19m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 3/17
11:35 am-4:55 pm
1 stop5h 20m
Chicago Midway
Wed 3/18
1:10 pm-6:28 pm
1 stop5h 18m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 3/5
7:05 am-11:59 am
1 stop4h 54m
Chicago Midway
Mon 3/9
9:35 am-3:03 pm
1 stop5h 28m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from Houston George Bush Intcntl Airport to Chicago, you should look to book at least 44 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, September is the cheapest month in which you can book a flight from Houston George Bush Intcntl Airport to Chicago (average of $60). Flying from Houston George Bush Intcntl Airport to Chicago in May is currently the most expensive (average of $95). 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.
When flying from Houston George Bush Intcntl Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 59% versus a flight at noon.
Travelers seeking maximum savings on their Houston George Bush Intcntl Airport to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from IAH to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).
About 12% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 153 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, United Airlines have had the lowest number of delays on this route, with just 11% of flights being delayed.
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Sebrena,Oct 2025
IAH - RSW
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Sebrena,Oct 2025
IAH - RSW
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Sebrena,Oct 2025
IAH - RSW
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Sebrena,Oct 2025
IAH - RSW
Crew
Overall
Food
Boarding
Entertainment
Comfort
Reviews
Sebrena,Oct 2025
IAH - RSW
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$189 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$80 | Average$162 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$157 | Average$266 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$170 | Average$346 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$216 | Average$331 | FlexibilityNo cancel fee | On-timeN/A |