Frontier's UpFront Plus seats offer a guaranteed empty middle seat for extra comfort.
Book early morning flights to avoid delays and ensure timely arrival.
Round-trip from | $90 (Trip.com) |
---|---|
One-way from | $48 (Cheapflightsfares) |
Popular in | March |
Cheapest in | September |
Average price | $183 |
Fly from
Fly to
Route
Depart
Return
Price
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Wed 5/7
10:40 am-1:17 pm
Nonstop2h 37m
Chicago Midway
Wed 5/21
12:21 pm-3:18 pm
Nonstop2h 57m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Fri 5/2
8:15 pm-10:58 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 5/4
6:00 am-8:53 am
Nonstop2h 53m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Fri 5/9
1:14 pm-3:57 pm
Nonstop2h 43m
Chicago O'Hare Intl
Tue 5/13
9:14 pm-11:59 pm
Nonstop2h 45m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Tue 5/13
9:10 am-11:50 am
Nonstop2h 40m
Chicago O'Hare Intl
Sat 5/17
9:14 pm-11:59 pm
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 5/7
7:15 am-9:40 am
Nonstop2h 25m
Chicago Midway
Wed 5/14
6:30 am-9:10 am
Nonstop2h 40m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Wed 5/7
10:40 am-1:29 pm
Nonstop2h 49m
Chicago O'Hare Intl
Wed 5/21
6:50 am-9:37 am
Nonstop2h 47m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 5/13
6:00 am-11:53 am
1 stop5h 53m
Chicago Midway
Wed 5/21
12:48 pm-5:57 pm
1 stop5h 09m
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Tue 5/13
5:06 pm-11:58 pm
1 stop6h 52m
Chicago O'Hare Intl
Wed 5/21
7:10 am-3:23 pm
1 stop8h 13m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 5/13
6:37 am-1:15 pm
1 stop6h 38m
Chicago Midway
Tue 5/20
9:16 am-3:23 pm
1 stop6h 07m
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Wed 5/7
2:45 pm-9:20 pm
1 stop6h 35m
Chicago O'Hare Intl
Sat 5/10
7:05 am-12:17 pm
1 stop5h 12m
To ensure you get the cheapest price possible for a flight from Houston to Chicago, you should look to book at least 80 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, August is the cheapest month in which you can book a flight from Houston to Chicago (average of $245). Flying from Houston to Chicago in March is currently the most expensive (average of $321). 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.
A simple way to save on the total cost of your ticket is to fly from Houston to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Houston to Chicago flight should consider departing on Wednesday evenings 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.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
You can land at Chicago O’Hare that’s on the northwest side of the city. It’s 14 miles from the busy Loop business sector. This is Chicago’s busiest airport. It serves flights that go to Europe, Africa, Asia, and North and South America. It’s the sixth busiest airport in the world.
Your other option is to land at Chicago Midway. This was once the city’s main airport until O’Hare came on the scene. The airport is still quite busy, serving more than 22 million passengers in 2018. The majority of the traffic coming through this airport is provided by Southwest Airlines.
Southwest has some other options between Hobby and Midway. They make stops in St. Louis, New Orleans, Orlando, Dallas, Oklahoma City, Nashville, Jacksonville, Austin, and a few others. Most of their stopovers are under an hour.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$51 | Average$142 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$62 | Average$150 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$144 | Average$247 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$148 | Average$339 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$195 | Average$346 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$196 | Average$406 | FlexibilityNo cancel fee | On-timeN/A |