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Cheap flights from Houston to Chicago from $54

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 11/10. 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

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Frontier Logo
10:04 am - 12:37 pmIAH-MDW
2h 33mnonstop
Frontier Logo
5:30 am - 8:19 amMDW-IAH
2h 49mnonstop
$97Frontier
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Fri, Oct 31 - Sun, Nov 2
Multiple Airlines Logo
12:13 pm - 2:51 pmIAH-ORD
2h 38mnonstop
Multiple Airlines Logo
1:36 pm - 4:33 pmORD-IAH
2h 57mnonstop
$98Multiple Airlines
Find Deal
Tue, Nov 4 - Thu, Nov 6
Spirit Airlines Logo
11:55 am - 2:29 pmIAH-ORD
2h 34mnonstop
Spirit Airlines Logo
5:10 am - 5:26 pmORD-IAH
12h 16m1 stop
$101Spirit Airlines
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Sat, Nov 8 - Wed, Nov 12
Spirit Airlines Logo
5:20 pm - 8:03 pmIAH-ORD
2h 43mnonstop
Spirit Airlines Logo
8:28 am - 11:18 amORD-IAH
2h 50mnonstop
$102Spirit Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 9
Southwest Logo
6:40 am - 9:05 amHOU-MDW
2h 25mnonstop
Southwest Logo
4:10 pm - 7:00 pmMDW-HOU
2h 50mnonstop
$117Southwest
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Thu, Jan 8 - Sun, Jan 11
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
Southwest Logo
5:55 am - 8:50 amMDW-HOU
2h 55mnonstop
$137Southwest
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Tue, Dec 16 - Sun, Jan 11
Delta Logo
6:00 am - 12:19 pmHOU-ORD
6h 19m1 stop
Delta Logo
6:45 am - 1:28 pmORD-HOU
6h 43m1 stop
$187Delta
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Tue, Nov 11 - Tue, Nov 18
Delta Logo
10:40 am - 4:38 pmHOU-MDW
5h 58m1 stop
Delta Logo
5:34 pm - 11:07 pmMDW-HOU
5h 33m1 stop
$197Delta
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Tue, Nov 18 - Thu, Nov 27
American Airlines Logo
6:00 am - 10:37 amHOU-ORD
4h 37m1 stop
American Airlines Logo
11:46 am - 5:54 pmORD-HOU
6h 08m1 stop
$243American Airlines
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Tue, Nov 18 - Tue, Nov 18
American Airlines Logo
5:44 am - 10:37 amHOU-ORD
4h 53m1 stop
American Airlines Logo
3:14 pm - 8:18 pmORD-HOU
5h 04m1 stop
$249American Airlines
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Wed, Dec 3 - Sat, Dec 6

Spirit Airlines flights from Houston to Chicago

Our best Spirit Airlines deals on Houston to Chicago flight tickets
Spirit Airlines
Nov 8
IAH11:55 amHouston George Bush Intcntl
2h 34m
ORD2:29 pmChicago O'Hare Intl
Nov 12
ORD5:10 amChicago O'Hare Intl
12h 16m
1 stop
IAH5:26 pmHouston George Bush Intcntl
$101
Find similar
Spirit Airlines
Oct 31
IAH5:20 pmHouston George Bush Intcntl
2h 43m
ORD8:03 pmChicago O'Hare Intl
Nov 9
ORD8:28 amChicago O'Hare Intl
2h 50m
IAH11:18 amHouston George Bush Intcntl
$102
Find similar
Spirit Airlines
Nov 5
IAH12:13 pmHouston George Bush Intcntl
2h 38m
ORD2:51 pmChicago O'Hare Intl
Dec 5
ORD8:52 pmChicago O'Hare Intl
2h 56m
IAH11:48 pmHouston George Bush Intcntl
$103
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Frontier flights from Houston to Chicago

Our best Frontier deals on Houston to Chicago flight tickets
Frontier
Oct 31
IAH10:04 amHouston George Bush Intcntl
2h 33m
MDW12:37 pmChicago Midway
Nov 2
MDW5:30 amChicago Midway
2h 49m
IAH8:19 amHouston George Bush Intcntl
$97
Find similar
Frontier
Nov 6
IAH10:04 amHouston George Bush Intcntl
2h 33m
MDW12:37 pmChicago Midway
Nov 9
MDW6:30 amChicago Midway
2h 49m
IAH9:19 amHouston George Bush Intcntl
$98
Find similar
Frontier
Nov 11
IAH5:28 pmHouston George Bush Intcntl
2h 46m
ORD8:14 pmChicago O'Hare Intl
Nov 17
ORD11:24 amChicago O'Hare Intl
10h 44m
1 stop
IAH10:08 pmHouston George Bush Intcntl
$99
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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 October 16, 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 - MDW

IAHMDW

Houston George Bush Intcntl

Fri 10/31

10:04 am-12:37 pm

Nonstop2h 33m

Chicago Midway

Sun 11/2

5:30 am-8:19 am

Nonstop2h 49m

$97

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Tue 11/4

12:13 pm-2:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

Thu 11/6

1:36 pm-4:33 pm

Nonstop2h 57m

$98

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Sat 11/8

11:55 am-2:29 pm

Nonstop2h 34m

Chicago O'Hare Intl

Wed 11/12

5:10 am-5:26 pm

1 stop12h 16m

$101

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Fri 10/31

5:20 pm-8:03 pm

Nonstop2h 43m

Chicago O'Hare Intl

Sun 11/9

8:28 am-11:18 am

Nonstop2h 50m

$102

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 1/8

6:40 am-9:05 am

Nonstop2h 25m

Chicago Midway

Sun 1/11

4:10 pm-7:00 pm

Nonstop2h 50m

$117

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 12/16

6:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Sun 1/11

5:55 am-8:50 am

Nonstop2h 55m

$137

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 11/11

6:00 am-12:19 pm

1 stop6h 19m

Chicago O'Hare Intl

Tue 11/18

6:45 am-1:28 pm

1 stop6h 43m

$187

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 11/18

10:40 am-4:38 pm

1 stop5h 58m

Chicago Midway

Thu 11/27

5:34 pm-11:07 pm

1 stop5h 33m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 11/18

6:00 am-10:37 am

1 stop4h 37m

Chicago O'Hare Intl

Tue 11/18

11:46 am-5:54 pm

1 stop6h 08m

$243

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/3

5:44 am-10:37 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 12/6

3:14 pm-8:18 pm

1 stop5h 04m

$249

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 February is, on average, the cheapest month to fly to Chicago from Houston, with most prices found around $177. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Houston to Chicago during September average around $182.

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 $271. 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 $413.

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 $206. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $810.

What is the cheapest Houston to Chicago flight route?

Fly from Houston George Bush Intcntl to Chicago Midway 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 $226 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 $179 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 $77Free CancellationRating
6.3
8,099 reviews
Search Spirit Airlines flights
FrontierPriceFrom $77Free CancellationRating
5.8
3,137 reviews
Search Frontier flights
American AirlinesPriceFrom $162Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
SouthwestPriceFrom $172Free CancellationRating
8.0
4,240 reviews
Search Southwest flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
8,982 reviews
Search United Airlines flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,982 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
Portage
Lansing
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