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 | $95 (FlightHub) |
One-way from | $50 (Super.com) |
Popular in | June |
Cheapest in | March |
Average price | $208 |
Good round-trip deal | $129 or less |
Good one-way deal | $84 or less |
Fly from
Fly to
Route
Depart
Return
Price
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
mié. 12/10
5:43 pm-8:09 pm
Nonstop2h 26m
Chicago O'Hare Intl
lun. 12/15
9:14 pm-11:59 pm
Nonstop2h 45m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
mié. 12/10
8:07 pm-9:58 pm
1 stop25h 51m
Chicago Midway
dom. 12/14
2:01 pm-5:08 pm
Nonstop3h 07m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
mié. 12/10
8:07 pm-9:58 pm
1 stop25h 51m
Chicago Midway
lun. 12/15
12:18 pm-12:31 am
1 stop12h 13m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
jue. 12/11
6:05 am-6:08 pm
1 stop12h 03m
Chicago Midway
lun. 12/15
12:18 pm-12:31 am
1 stop12h 13m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
vie. 2/27
3:08 pm-8:44 pm
1 stop5h 36m
Chicago O'Hare Intl
dom. 3/1
5:25 am-11:35 am
1 stop6h 10m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
mar. 1/27
7:05 am-11:59 am
1 stop4h 54m
Chicago Midway
mar. 2/3
6:00 am-11:31 am
1 stop5h 31m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
mié. 1/7
4:25 pm-10:07 pm
1 stop5h 42m
Chicago Midway
vie. 1/9
5:31 pm-11:56 pm
1 stop6h 25m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
mié. 1/28
12:20 pm-5:55 pm
1 stop5h 35m
Chicago Midway
vie. 1/30
9:50 am-3:54 pm
1 stop6h 04m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
mié. 2/11
7:05 am-11:59 am
1 stop4h 54m
Chicago Midway
mié. 2/11
6:14 pm-11:56 pm
1 stop5h 42m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
jue. 1/15
12:20 pm-5:34 pm
1 stop5h 14m
Chicago Midway
sáb. 1/17
6:45 am-12:48 pm
1 stop6h 03m
| 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 Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| 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 73 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 January is currently the most expensive (average of $116). 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 61% versus a flight at noon.
Travelers seeking maximum savings on their Houston George Bush Intcntl Airport to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday at noon 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 Wednesday (58 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (17 on average).
About 12% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 154 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, CommutAir have had the lowest number of delays on this route, with no flights being classified as delayed.
Comfort
Food
Overall
Boarding
Crew
Entertainment
Reviews
Sebrena,Oct 2025
IAH - RSW
Comfort
Food
Overall
Boarding
Crew
Entertainment
Reviews
Sebrena,Oct 2025
IAH - RSW
Comfort
Food
Overall
Boarding
Crew
Entertainment
Reviews
Sebrena,Oct 2025
IAH - RSW
Comfort
Food
Overall
Boarding
Crew
Entertainment
Reviews
Sebrena,Oct 2025
IAH - RSW
Comfort
Food
Overall
Boarding
Crew
Entertainment
Reviews
Sebrena,Oct 2025
IAH - RSW
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$186 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$169 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$159 | Average$268 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$355 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$216 | Average$346 | FlexibilityNo cancel fee | On-timeN/A |