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Cheap flights from Houston to Chicago from $53

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Houston to Chicago departing on 12/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Spirit Airlines Logo
12:47 pm - 10:48 pmIAH-ORD
10h 01m1 stop
Spirit Airlines Logo
2:04 pm - 4:50 pmORD-IAH
2h 46mnonstop
$97Spirit Airlines
Find Deal
Wed, Sep 17 - Wed, Sep 24
Frontier Logo
6:09 pm - 8:46 pmIAH-MDW
2h 37mnonstop
Frontier Logo
2:26 pm - 5:14 pmMDW-IAH
2h 48mnonstop
$97Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
6:09 pm - 8:46 pmIAH-MDW
2h 37mnonstop
Frontier Logo
6:30 am - 9:18 amMDW-IAH
2h 48mnonstop
$98Frontier
Find Deal
Fri, Sep 5 - Sun, Sep 7
Spirit Airlines Logo
5:05 pm - 7:50 pmIAH-ORD
2h 45mnonstop
Spirit Airlines Logo
11:57 am - 10:42 pmORD-IAH
10h 45m1 stop
$102Spirit Airlines
Find Deal
Mon, Sep 8 - Wed, Sep 10
Southwest Logo
4:20 pm - 6:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
7:20 pm - 9:50 pmMDW-HOU
2h 30mnonstop
$157Southwest
Find Deal
Sat, Sep 20 - Sat, Sep 27
Southwest Logo
10:25 pm - 12:45 amHOU-MDW
2h 20mnonstop
Southwest Logo
5:15 am - 7:50 amMDW-HOU
2h 35mnonstop
$177Southwest
Find Deal
Mon, Oct 27 - Tue, Oct 28
Delta Logo
1:13 pm - 9:10 pmHOU-MDW
7h 57m1 stop
Delta Logo
10:35 am - 5:40 pmMDW-HOU
7h 05m1 stop
$217Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
Delta Logo
10:44 am - 4:31 pmHOU-ORD
5h 47m1 stop
Delta Logo
5:51 pm - 11:00 pmORD-HOU
5h 09m1 stop
$217Delta
Find Deal
Sat, Oct 4 - Mon, Oct 6
American Airlines Logo
6:00 am - 11:00 amHOU-ORD
5h 00m1 stop
American Airlines Logo
1:20 pm - 6:10 pmORD-HOU
4h 50m1 stop
$251American Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 3
American Airlines Logo
4:26 pm - 9:45 pmHOU-ORD
5h 19m1 stop
American Airlines Logo
1:20 pm - 6:10 pmORD-HOU
4h 50m1 stop
$256American Airlines
Find Deal
Tue, Sep 9 - Wed, Sep 17

Frontier flights from Houston to Chicago

Our best Frontier deals on Houston to Chicago flight tickets
Frontier
Sep 5
IAH6:09 pmHouston George Bush Intcntl
2h 37m
MDW8:46 pmChicago Midway
Sep 8
MDW2:26 pmChicago Midway
2h 48m
IAH5:14 pmHouston George Bush Intcntl
$97
Find similar
Frontier
Sep 5
IAH6:09 pmHouston George Bush Intcntl
2h 37m
MDW8:46 pmChicago Midway
Sep 7
MDW6:30 amChicago Midway
2h 48m
IAH9:18 amHouston George Bush Intcntl
$98
Find similar
Frontier
Sep 26
IAH8:00 pmHouston George Bush Intcntl
2h 45m
ORD10:45 pmChicago O'Hare Intl
Sep 29
ORD4:03 pmChicago O'Hare Intl
3h 07m
IAH7:10 pmHouston George Bush Intcntl
$99
Find similar

Spirit Airlines flights from Houston to Chicago

Our best Spirit Airlines deals on Houston to Chicago flight tickets
Spirit Airlines
Sep 17
IAH12:47 pmHouston George Bush Intcntl
10h 01m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 24
ORD2:04 pmChicago O'Hare Intl
2h 46m
IAH4:50 pmHouston George Bush Intcntl
$97
Find similar
Spirit Airlines
Sep 8
IAH5:05 pmHouston George Bush Intcntl
2h 45m
ORD7:50 pmChicago O'Hare Intl
Sep 10
ORD11:57 amChicago O'Hare Intl
10h 45m
1 stop
IAH10:42 pmHouston George Bush Intcntl
$102
Find similar
Spirit Airlines
Sep 3
IAH5:02 pmHouston George Bush Intcntl
2h 40m
ORD7:42 pmChicago O'Hare Intl
Sep 10
ORD2:04 pmChicago O'Hare Intl
2h 46m
IAH4:50 pmHouston George Bush Intcntl
$103
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Houston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Houston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Wed 9/17

12:47 pm-10:48 pm

1 stop10h 01m

Chicago O'Hare Intl

Wed 9/24

2:04 pm-4:50 pm

Nonstop2h 46m

$97

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 9/5

6:09 pm-8:46 pm

Nonstop2h 37m

Chicago Midway

Mon 9/8

2:26 pm-5:14 pm

Nonstop2h 48m

$97

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 9/5

6:09 pm-8:46 pm

Nonstop2h 37m

Chicago Midway

Sun 9/7

6:30 am-9:18 am

Nonstop2h 48m

$98

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Mon 9/8

5:05 pm-7:50 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 9/10

11:57 am-10:42 pm

1 stop10h 45m

$102

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/20

4:20 pm-6:45 pm

Nonstop2h 25m

Chicago Midway

Sat 9/27

7:20 pm-9:50 pm

Nonstop2h 30m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 10/27

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

Tue 10/28

5:15 am-7:50 am

Nonstop2h 35m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/13

1:13 pm-9:10 pm

1 stop7h 57m

Chicago Midway

Wed 9/17

10:35 am-5:40 pm

1 stop7h 05m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 10/4

10:44 am-4:31 pm

1 stop5h 47m

Chicago O'Hare Intl

Mon 10/6

5:51 pm-11:00 pm

1 stop5h 09m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 9/3

6:00 am-11:00 am

1 stop5h 00m

Chicago O'Hare Intl

Wed 9/3

1:20 pm-6:10 pm

1 stop4h 50m

$251

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 9/9

4:26 pm-9:45 pm

1 stop5h 19m

Chicago O'Hare Intl

Wed 9/17

1:20 pm-6:10 pm

1 stop4h 50m

$256

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Houston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Houston and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Houston, with most prices found around $162. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Houston to Chicago during October average around $164.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $268. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Houston to Chicago for around $389.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Houston to Chicago during this time can be as low as $198. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $797.

What is the cheapest Houston to Chicago flight route?

Fly from Houston George Bush Intcntl to Chicago O'Hare Intl for the best Houston - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Houston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $223 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Houston for as low as $158 on momondo.

What cabin class options are available on Houston to Chicago flights?

There are 4 cabin classes available to choose from on Houston to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Houston to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Houston to Chicago

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from Houston to Chicago takes 2h 20m
Direct flights go from Houston to Chicago every day.
There is 1 airport near Chicago: Chicago Midway (MDW)
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  • How far is Houston to Chicago by plane?

    A flight from Houston to Chicago will travel around 941.3 mi. 2h 20m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Houston to Chicago?

    Prices for flights from Houston to Chicago refresh daily.

  • How many operators does momondo search for flights from Houston to Chicago?

  • How old do you have to be to fly from Houston to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Houston to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Houston to Chicago

Compare and see reviews for airlines that fly from Houston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $64Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
FrontierPriceFrom $68Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
American AirlinesPriceFrom $157Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,981 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Houston to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Houston to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Houston to Chicago with flexible booking policies on momondo?

All flight searches from Houston to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Houston to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Houston.

I’m not ready to book a flight from Houston to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Houston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport