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Cheap flights from Houston to Chicago from $50

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 10/3. 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
4:29 pm - 7:16 pmIAH-ORD
2h 47mnonstop
Spirit Airlines Logo
7:35 am - 10:20 amORD-IAH
2h 45mnonstop
$90Spirit Airlines
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Sat, Nov 8 - Tue, Nov 18
Frontier Logo
5:42 pm - 11:39 pmIAH-ORD
5h 57m1 stop
Frontier Logo
1:14 pm - 4:11 pmORD-IAH
2h 57mnonstop
$95Frontier
Find Deal
Mon, Oct 20 - Sat, Oct 25
Frontier Logo
8:00 pm - 10:45 pmIAH-ORD
2h 45mnonstop
Frontier Logo
4:03 pm - 7:10 pmORD-IAH
3h 07mnonstop
$100Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Spirit Airlines Logo
4:29 pm - 7:16 pmIAH-ORD
2h 47mnonstop
Spirit Airlines Logo
7:35 am - 10:20 amORD-IAH
2h 45mnonstop
$103Spirit Airlines
Find Deal
Wed, Nov 12 - Fri, Nov 14
Southwest Logo
5:55 pm - 8:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
7:45 pm - 10:20 pmMDW-HOU
2h 35mnonstop
$157Southwest
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Sat, Oct 18 - Sat, Oct 25
Southwest Logo
5:55 pm - 8:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:25 am - 12:30 pmMDW-HOU
4h 05m1 stop
$163Southwest
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Sat, Oct 18 - Sat, Oct 25
Delta Logo
1:13 pm - 7:05 pmHOU-ORD
5h 52m1 stop
Delta Logo
11:23 am - 5:48 pmORD-HOU
6h 25m1 stop
$233Delta
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Sat, Oct 4 - Wed, Oct 8
Delta Logo
2:22 pm - 9:24 pmHOU-ORD
7h 02m1 stop
Delta Logo
11:23 am - 5:48 pmORD-HOU
6h 25m1 stop
$237Delta
Find Deal
Mon, Oct 6 - Wed, Oct 8
American Airlines Logo
10:08 am - 5:12 pmHOU-ORD
7h 04m1 stop
American Airlines Logo
10:24 am - 3:53 pmORD-HOU
5h 29m1 stop
$271American Airlines
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Fri, Dec 12 - Tue, Dec 16
American Airlines Logo
6:44 pm - 11:59 pmHOU-ORD
5h 15m1 stop
American Airlines Logo
4:10 pm - 10:02 pmORD-HOU
5h 52m1 stop
$303American Airlines
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Fri, Oct 3 - Mon, Oct 6

Spirit Airlines flights from Houston to Chicago

Our best Spirit Airlines deals on Houston to Chicago flight tickets
Spirit Airlines
Nov 8
IAH4:29 pmHouston George Bush Intcntl
2h 47m
ORD7:16 pmChicago O'Hare Intl
Nov 18
ORD7:35 amChicago O'Hare Intl
2h 45m
IAH10:20 amHouston George Bush Intcntl
$90
Find similar
Spirit Airlines
Nov 12
IAH4:29 pmHouston George Bush Intcntl
2h 47m
ORD7:16 pmChicago O'Hare Intl
Nov 14
ORD7:35 amChicago O'Hare Intl
2h 45m
IAH10:20 amHouston George Bush Intcntl
$103
Find similar
Spirit Airlines
Sep 30
IAH10:23 amHouston George Bush Intcntl
2h 46m
ORD1:09 pmChicago O'Hare Intl
Oct 3
ORD8:56 pmChicago O'Hare Intl
2h 49m
IAH11:45 pmHouston George Bush Intcntl
$105
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Delta flights from Houston to Chicago

Our best Delta deals on Houston to Chicago flight tickets
Delta
Oct 4
HOU1:13 pmHouston Hobby
5h 52m
1 stop
ORD7:05 pmChicago O'Hare Intl
Oct 8
ORD11:23 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:48 pmHouston Hobby
$233
Find similar
Delta
Oct 6
HOU2:22 pmHouston Hobby
7h 02m
1 stop
ORD9:24 pmChicago O'Hare Intl
Oct 8
ORD11:23 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:48 pmHouston Hobby
$237
Find similar
Delta
Oct 1
HOU1:13 pmHouston Hobby
5h 47m
1 stop
ORD7:00 pmChicago O'Hare Intl
Oct 4
ORD11:15 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:40 pmHouston Hobby
$257
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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 September 17, 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

Sat 11/8

4:29 pm-7:16 pm

Nonstop2h 47m

Chicago O'Hare Intl

Tue 11/18

7:35 am-10:20 am

Nonstop2h 45m

$90

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Mon 10/20

5:42 pm-11:39 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 10/25

1:14 pm-4:11 pm

Nonstop2h 57m

$95

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Fri 10/3

8:00 pm-10:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 10/6

4:03 pm-7:10 pm

Nonstop3h 07m

$100

HoustonChicago

IAH - ORD

IAHORD

Houston George Bush Intcntl

Wed 11/12

4:29 pm-7:16 pm

Nonstop2h 47m

Chicago O'Hare Intl

Fri 11/14

7:35 am-10:20 am

Nonstop2h 45m

$103

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/18

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

Sat 10/25

7:45 pm-10:20 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/18

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

Sat 10/25

8:25 am-12:30 pm

1 stop4h 05m

$163

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 10/4

1:13 pm-7:05 pm

1 stop5h 52m

Chicago O'Hare Intl

Wed 10/8

11:23 am-5:48 pm

1 stop6h 25m

$233

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 10/6

2:22 pm-9:24 pm

1 stop7h 02m

Chicago O'Hare Intl

Wed 10/8

11:23 am-5:48 pm

1 stop6h 25m

$237

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 12/12

10:08 am-5:12 pm

1 stop7h 04m

Chicago O'Hare Intl

Tue 12/16

10:24 am-3:53 pm

1 stop5h 29m

$271

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 10/3

6:44 pm-11:59 pm

1 stop5h 15m

Chicago O'Hare Intl

Mon 10/6

4:10 pm-10:02 pm

1 stop5h 52m

$303

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 October is, on average, the cheapest month to fly to Chicago from Houston, with most prices found around $168. If you’re not able to fly to Chicago in October, then February is your next best option. Flight prices from Houston to Chicago during February average around $177.

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 $270. 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 $204. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $811.

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 $147 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 $71Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
FrontierPriceFrom $75Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
American AirlinesPriceFrom $160Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,961 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