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Cheap flights from Houston Hobby Airport to Chicago from $59

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 1/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Houston Hobby Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:15 pm - 4:40 pmHOU-MDW
2h 25mnonstop
Southwest Logo
5:55 am - 8:50 amMDW-HOU
2h 55mnonstop
$117Southwest
Find Deal
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
Southwest Logo
7:00 am - 9:40 amMDW-HOU
2h 40mnonstop
$157Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
7:45 pm - 10:10 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:35 pm - 11:20 pmMDW-HOU
2h 45mnonstop
$158Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
6:35 am - 9:00 amHOU-MDW
2h 25mnonstop
Southwest Logo
5:10 am - 7:55 amMDW-HOU
2h 45mnonstop
$177Southwest
Find Deal
Wed, Dec 10 - Sun, Dec 14
Delta Logo
10:40 am - 4:46 pmHOU-ORD
6h 06m1 stop
Delta Logo
5:23 am - 1:28 pmORD-HOU
8h 05m1 stop
$197Delta
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Mon, Nov 24 - Thu, Nov 27
Delta Logo
6:47 pm - 12:01 amHOU-ORD
5h 14m1 stop
Delta Logo
4:20 pm - 10:33 pmORD-HOU
6h 13m1 stop
$207Delta
Find Deal
Thu, Dec 4 - Sat, Dec 6
American Airlines Logo
6:36 pm - 11:44 pmHOU-ORD
5h 08m1 stop
American Airlines Logo
6:54 am - 12:09 pmORD-HOU
5h 15m1 stop
$269American Airlines
Find Deal
Wed, Jan 7 - Fri, Jan 9
Sun Country Air Logo
6:37 pm - 9:57 amHOU-ORD
15h 20m1 stop
Sun Country Air Logo
11:00 am - 5:25 pmORD-HOU
6h 25m1 stop
$292Sun Country Air
Find Deal
Tue, Nov 25 - Fri, Nov 28
Sun Country Air Logo
8:01 pm - 8:20 amHOU-ORD
12h 19m1 stop
Sun Country Air Logo
11:00 am - 5:25 pmORD-HOU
6h 25m1 stop
$294Sun Country Air
Find Deal
Wed, Nov 26 - Fri, Nov 28
American Airlines Logo
5:44 am - 10:40 amHOU-ORD
4h 56m1 stop
American Airlines Logo
5:18 am - 11:45 amORD-HOU
6h 27m1 stop
$303American Airlines
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Wed, Dec 3 - Sun, Dec 7

Delta flights from Houston Hobby Airport to Chicago

Our best Delta deals on Houston Hobby Airport to Chicago flight tickets
Delta
Nov 24
HOU10:40 amHouston Hobby
6h 06m
1 stop
ORD4:46 pmChicago O'Hare Intl
Nov 27
ORD5:23 amChicago O'Hare Intl
8h 05m
1 stop
HOU1:28 pmHouston Hobby
$197
Find similar
Delta
Dec 4
HOU6:47 pmHouston Hobby
5h 14m
1 stop
ORD12:01 amChicago O'Hare Intl
Dec 6
ORD4:20 pmChicago O'Hare Intl
6h 13m
1 stop
HOU10:33 pmHouston Hobby
$207
Find similar
Delta
Dec 12
HOU6:47 pmHouston Hobby
5h 14m
1 stop
ORD12:01 amChicago O'Hare Intl
Dec 14
ORD6:45 amChicago O'Hare Intl
6h 43m
1 stop
HOU1:28 pmHouston Hobby
$217
Find similar

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
Nov 25
HOU6:37 pmHouston Hobby
15h 20m
1 stop
ORD9:57 amChicago O'Hare Intl
Nov 28
ORD11:00 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:25 pmHouston Hobby
$292
Find similar
Sun Country Air
Nov 26
HOU8:01 pmHouston Hobby
12h 19m
1 stop
ORD8:20 amChicago O'Hare Intl
Nov 28
ORD11:00 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:25 pmHouston Hobby
$294
Find similar
Sun Country Air
Nov 25
HOU6:37 pmHouston Hobby
15h 20m
1 stop
ORD9:57 amChicago O'Hare Intl
Nov 28
ORD11:00 amChicago O'Hare Intl
6h 25m
1 stop
HOU5:25 pmHouston Hobby
$304
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 November 4, 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

Thu 1/8

2:15 pm-4:40 pm

Nonstop2h 25m

Chicago Midway

Sun 1/11

5:55 am-8:50 am

Nonstop2h 55m

$117

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/3

6:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Wed 12/10

7:00 am-9:40 am

Nonstop2h 40m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 12/2

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Tue 12/9

8:35 pm-11:20 pm

Nonstop2h 45m

$158

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/10

6:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Sun 12/14

5:10 am-7:55 am

Nonstop2h 45m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 11/24

10:40 am-4:46 pm

1 stop6h 06m

Chicago O'Hare Intl

Thu 11/27

5:23 am-1:28 pm

1 stop8h 05m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 12/4

6:47 pm-12:01 am

1 stop5h 14m

Chicago O'Hare Intl

Sat 12/6

4:20 pm-10:33 pm

1 stop6h 13m

$207

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 1/7

6:36 pm-11:44 pm

1 stop5h 08m

Chicago O'Hare Intl

Fri 1/9

6:54 am-12:09 pm

1 stop5h 15m

$269

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 11/25

6:37 pm-9:57 am

1 stop15h 20m

Chicago O'Hare Intl

Fri 11/28

11:00 am-5:25 pm

1 stop6h 25m

$292

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 11/26

8:01 pm-8:20 am

1 stop12h 19m

Chicago O'Hare Intl

Fri 11/28

11:00 am-5:25 pm

1 stop6h 25m

$294

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/3

5:44 am-10:40 am

1 stop4h 56m

Chicago O'Hare Intl

Sun 12/7

5:18 am-11:45 am

1 stop6h 27m

$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 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 typical price of a round-trip flight between Houston Hobby Airport 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 Hobby Airport, 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 Hobby Airport 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 $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 $387.

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 $207. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $773.

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 $178 on momondo.

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

There is only 1 cabin class 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 November 2025, prices for Houston Hobby Airport to Chicago flights are approximately 20% 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

$138

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Houston Hobby Airport in the past 72 hours is $138. The best round-trip flight deal from Houston Hobby Airport to Chicago found on momondo in the last 72 hours is $208.
The fastest flight from Houston Hobby Airport to Chicago takes 2h 20m
Direct flights go from Houston Hobby Airport to Chicago every day.
There is 1 airport near Chicago: 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 25m 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 $77Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
FrontierPriceFrom $77Free CancellationRating
5.8
3,117 reviews
Search Frontier flights
SouthwestPriceFrom $171Free CancellationRating
8.0
4,239 reviews
Search Southwest flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
9,002 reviews
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.2
11,040 reviews
Search American Airlines 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 $171. Generally, Southwest has 18 flights on this route every week with an average price of $281. 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