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Cheap flights from Houston Hobby Airport to Chicago from $79

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 Hobby Airport to Chicago departing on 8/30. 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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Find the cheapest flights from Houston Hobby Airport to Chicago

Cheap round-trip flights

Southwest Logo
1:25 pm - 3:50 pmHOU-MDW
2h 25mnonstop
Southwest Logo
10:10 am - 12:45 pmMDW-HOU
2h 35mnonstop
$157Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
5:45 am - 8:15 amMDW-HOU
2h 30mnonstop
$177Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
Southwest Logo
8:55 pm - 11:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:10 am - 11:45 amMDW-HOU
2h 35mnonstop
$187Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
11:25 am - 3:20 pmMDW-HOU
3h 55m1 stop
$197Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
Delta Logo
10:22 am - 3:28 pmHOU-MDW
5h 06m1 stop
Delta Logo
4:25 pm - 10:31 pmMDW-HOU
6h 06m1 stop
$217Delta
Find Deal
Sat, Aug 23 - Wed, Aug 27
Delta Logo
6:00 am - 12:17 pmHOU-ORD
6h 17m1 stop
Delta Logo
5:45 am - 12:10 pmORD-HOU
6h 25m1 stop
$217Delta
Find Deal
Sat, Aug 23 - Wed, Aug 27
Sun Country Air Logo
5:53 pm - 12:32 pmHOU-ORD
18h 39m1 stop
Sun Country Air Logo
8:00 am - 5:19 pmORD-HOU
9h 19m1 stop
$262Sun Country Air
Find Deal
Thu, Aug 21 - Sun, Aug 24
Sun Country Air Logo
9:33 am - 6:40 pmHOU-ORD
9h 07m1 stop
Sun Country Air Logo
11:00 am - 5:25 pmORD-HOU
6h 25m1 stop
$269Sun Country Air
Find Deal
Sun, Nov 23 - Fri, Nov 28
American Airlines Logo
6:00 am - 12:22 pmHOU-ORD
6h 22m1 stop
American Airlines Logo
2:55 pm - 7:59 pmORD-HOU
5h 04m1 stop
$305American Airlines
Find Deal
Sat, Aug 16 - Tue, Aug 26
American Airlines Logo
6:00 am - 12:22 pmHOU-ORD
6h 22m1 stop
American Airlines Logo
5:20 pm - 10:02 pmORD-HOU
4h 42m1 stop
$322American Airlines
Find Deal
Wed, Aug 27 - Fri, Aug 29

Sun Country Air flights from Houston Hobby Airport to Chicago

Our best Sun Country Air deals on Houston Hobby Airport to Chicago flight tickets
Sun Country Air
Aug 21
HOU5:53 pmHouston Hobby
18h 39m
1 stop
ORD12:32 pmChicago O'Hare Intl
Aug 24
ORD8:00 amChicago O'Hare Intl
9h 19m
1 stop
HOU5:19 pmHouston Hobby
$262
Find similar
Sun Country Air
Nov 23
HOU9:33 amHouston Hobby
9h 07m
1 stop
ORD6:40 pmChicago O'Hare Intl
Nov 28
ORD11:00 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:25 pmHouston Hobby
$269
Find similar
Sun Country Air
Aug 21
HOU5:53 pmHouston Hobby
18h 39m
1 stop
ORD12:32 pmChicago O'Hare Intl
Aug 24
ORD8:00 amChicago O'Hare Intl
9h 19m
1 stop
HOU5:19 pmHouston Hobby
$315
Find similar

American Airlines flights from Houston Hobby Airport to Chicago

Our best American Airlines deals on Houston Hobby Airport to Chicago flight tickets
American Airlines
Aug 13
HOU10:14 amHouston Hobby
4h 33m
1 stop
ORD2:47 pmChicago O'Hare Intl
Aug 16
ORD2:55 pmChicago O'Hare Intl
5h 04m
1 stop
HOU7:59 pmHouston Hobby
$257
Find similar
American Airlines
Aug 15
HOU6:00 amHouston Hobby
4h 44m
1 stop
ORD10:44 amChicago O'Hare Intl
Aug 26
ORD2:55 pmChicago O'Hare Intl
5h 04m
1 stop
HOU7:59 pmHouston Hobby
$305
Find similar
American Airlines
Aug 27
HOU6:00 amHouston Hobby
6h 22m
1 stop
ORD12:22 pmChicago O'Hare Intl
Aug 29
ORD5:20 pmChicago O'Hare Intl
4h 42m
1 stop
HOU10:02 pmHouston Hobby
$322
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Houston Hobby Airport 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 1, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 9/3

1:25 pm-3:50 pm

Nonstop2h 25m

Chicago Midway

Sat 9/6

10:10 am-12:45 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/6

8:20 pm-10:45 pm

Nonstop2h 25m

Chicago Midway

Mon 9/8

5:45 am-8:15 am

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 8/27

8:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 9/3

9:10 am-11:45 am

Nonstop2h 35m

$187

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 8/30

8:20 pm-10:45 pm

Nonstop2h 25m

Chicago Midway

Tue 9/2

11:25 am-3:20 pm

1 stop3h 55m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 8/23

10:22 am-3:28 pm

1 stop5h 06m

Chicago Midway

Wed 8/27

4:25 pm-10:31 pm

1 stop6h 06m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 8/23

6:00 am-12:17 pm

1 stop6h 17m

Chicago O'Hare Intl

Wed 8/27

5:45 am-12:10 pm

1 stop6h 25m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 8/21

5:53 pm-12:32 pm

1 stop18h 39m

Chicago O'Hare Intl

Sun 8/24

8:00 am-5:19 pm

1 stop9h 19m

$262

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sun 11/23

9:33 am-6:40 pm

1 stop9h 07m

Chicago O'Hare Intl

Fri 11/28

11:00 am-5:25 pm

1 stop6h 25m

$269

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 8/16

6:00 am-12:22 pm

1 stop6h 22m

Chicago O'Hare Intl

Tue 8/26

2:55 pm-7:59 pm

1 stop5h 04m

$305

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/27

6:00 am-12:22 pm

1 stop6h 22m

Chicago O'Hare Intl

Fri 8/29

5:20 pm-10:02 pm

1 stop4h 42m

$322

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 Hobby Airport 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 cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Houston Hobby Airport, with most prices found around $158. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Houston Hobby Airport to Chicago during September average around $158.

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 Hobby Airport to Chicago for around $418.

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 Hobby Airport to Chicago during this time can be as low as $194. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $759.

What is the cheapest Houston Hobby to Chicago flight route?

Fly from Houston Hobby to Chicago Midway for the best Houston Hobby - 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 Hobby Airport 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 Hobby Airport for as low as $147 on momondo.

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

There are 1 cabin classes available to choose from on Houston Hobby to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Houston Hobby Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Houston Hobby Airport to Chicago.

How have Houston Hobby Airport to Chicago flight prices changed over time?

As of August 2025, prices for Houston Hobby Airport to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

When to book flights from Houston Hobby Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Houston Hobby Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Houston Hobby Airport to Chicago (HOU to CHI) flight deals and tips

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

Best Price Found

$79

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Houston Hobby Airport in the past 72 hours is $79. The best round-trip flight deal from Houston Hobby Airport to Chicago found on momondo in the last 72 hours is $157.
The fastest flight from Houston Hobby Airport to Chicago takes 2h 20m
Direct flights go from Houston Hobby Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Houston Hobby to Chicago by plane?

    The straight-line distance from Houston Hobby to Chicago is 945.8 mi. 2h 20m is a normal flight duration for this route.

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

    Prices for flights from Houston Hobby Airport to Chicago are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Houston Hobby Airport to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Houston Hobby Airport to Chicago?

  • What is the most popular airline from Houston Hobby Airport to Chicago?

Best airlines flying from Houston Hobby Airport to Chicago

Compare and see reviews for airlines that fly from Houston Hobby Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $64Free CancellationRating
6.3
8,054 reviews
Search Spirit Airlines flights
FrontierPriceFrom $64Free CancellationRating
5.8
3,241 reviews
Search Frontier flights
American AirlinesPriceFrom $160Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
8,904 reviews
Search United Airlines flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Houston Hobby Airport to Chicago

    The lowest priced Southwest flight from Houston Hobby Airport to Chicago from the last 72 hours was $177. Generally, Southwest has 26 flights on this route every week with an average price of $289. Southwest is rated 8.0/10 by our users.

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?

If you are not ready to book a flight from Houston to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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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