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Cheap flights from Houston Hobby Airport to Chicago from $89

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 10/9. 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

Southwest Logo
8:45 am - 4:25 pmHOU-ORD
7h 40m1 stop
Southwest Logo
1:50 pm - 7:55 pmORD-HOU
6h 05m1 stop
$177Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25
Southwest Logo
4:30 pm - 9:30 pmHOU-ORD
5h 00m1 stop
Southwest Logo
3:10 pm - 11:00 pmORD-HOU
7h 50m1 stop
$182Southwest
Find Deal
Tue, Oct 14 - Wed, Oct 15
Southwest Logo
6:00 am - 2:00 pmHOU-ORD
8h 00m2 stops
Southwest Logo
12:40 pm - 7:30 pmORD-HOU
6h 50m2 stops
$187Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25
Southwest Logo
5:55 am - 1:30 pmHOU-ORD
7h 35m1 stop
Southwest Logo
2:15 pm - 8:10 pmORD-HOU
5h 55m1 stop
$197Southwest
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
6:44 pm - 11:58 pmHOU-ORD
5h 14m1 stop
Delta Logo
6:45 am - 1:27 pmORD-HOU
6h 42m1 stop
$217Delta
Find Deal
Thu, Oct 23 - Sat, Oct 25
Delta Logo
10:44 am - 4:31 pmHOU-ORD
5h 47m1 stop
Delta Logo
6:45 am - 1:27 pmORD-HOU
6h 42m1 stop
$233Delta
Find Deal
Sat, Oct 4 - Wed, Oct 15
Sun Country Air Logo
9:33 am - 10:45 amHOU-ORD
25h 12m1 stop
Sun Country Air Logo
11:42 am - 6:49 pmORD-HOU
7h 07m1 stop
$239Sun Country Air
Find Deal
Sun, Nov 16 - Mon, Nov 24
Sun Country Air Logo
6:25 pm - 9:02 amHOU-ORD
14h 37m1 stop
Sun Country Air Logo
9:18 am - 6:49 pmORD-HOU
9h 31m1 stop
$260Sun Country Air
Find Deal
Fri, Nov 28 - Mon, Dec 1
American Airlines Logo
10:16 am - 3:26 pmHOU-ORD
5h 10m1 stop
American Airlines Logo
5:00 am - 11:27 amORD-HOU
6h 27m1 stop
$269American Airlines
Find Deal
Wed, Jan 7 - Fri, Jan 9
American Airlines Logo
4:28 pm - 9:45 pmHOU-ORD
5h 17m1 stop
American Airlines Logo
1:20 pm - 6:10 pmORD-HOU
4h 50m1 stop
$287American Airlines
Find Deal
Sat, Sep 27 - Tue, Sep 30

American Airlines flights from Houston Hobby Airport to Chicago O'Hare Intl Airport

Our best American Airlines deals on Houston Hobby Airport to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jan 7
HOU10:16 amHouston Hobby
5h 10m
1 stop
ORD3:26 pmChicago O'Hare Intl
Jan 9
ORD5:00 amChicago O'Hare Intl
6h 27m
1 stop
HOU11:27 amHouston Hobby
$269
Find similar
American Airlines
Sep 27
HOU4:28 pmHouston Hobby
5h 17m
1 stop
ORD9:45 pmChicago O'Hare Intl
Sep 30
ORD1:20 pmChicago O'Hare Intl
4h 50m
1 stop
HOU6:10 pmHouston Hobby
$287
Find similar
American Airlines
Sep 28
HOU6:22 pmHouston Hobby
5h 30m
1 stop
ORD11:52 pmChicago O'Hare Intl
Oct 2
ORD8:25 amChicago O'Hare Intl
7h 34m
1 stop
HOU3:59 pmHouston Hobby
$328
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Southwest flights from Houston Hobby Airport to Chicago O'Hare Intl Airport

Our best Southwest deals on Houston Hobby Airport to Chicago O'Hare Intl Airport flight tickets
Southwest
Oct 22
HOU8:45 amHouston Hobby
7h 40m
1 stop
ORD4:25 pmChicago O'Hare Intl
Oct 25
ORD1:50 pmChicago O'Hare Intl
6h 05m
1 stop
HOU7:55 pmHouston Hobby
$177
Find similar
Southwest
Oct 14
HOU4:30 pmHouston Hobby
5h 00m
1 stop
ORD9:30 pmChicago O'Hare Intl
Oct 15
ORD3:10 pmChicago O'Hare Intl
7h 50m
1 stop
HOU11:00 pmHouston Hobby
$182
Find similar
Southwest
Oct 22
HOU6:00 amHouston Hobby
8h 00m
2 stops
ORD2:00 pmChicago O'Hare Intl
Oct 25
ORD12:40 pmChicago O'Hare Intl
6h 50m
2 stops
HOU7:30 pmHouston Hobby
$187
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Houston Hobby Airport to Chicago O'Hare Intl Airport 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 16, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 10/22

8:45 am-4:25 pm

1 stop7h 40m

Chicago O'Hare Intl

Sat 10/25

1:50 pm-7:55 pm

1 stop6h 05m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 10/14

4:30 pm-9:30 pm

1 stop5h 00m

Chicago O'Hare Intl

Wed 10/15

3:10 pm-11:00 pm

1 stop7h 50m

$182

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 10/22

6:00 am-2:00 pm

2 stops8h 00m

Chicago O'Hare Intl

Sat 10/25

12:40 pm-7:30 pm

2 stops6h 50m

$187

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 11/14

5:55 am-1:30 pm

1 stop7h 35m

Chicago O'Hare Intl

Mon 11/17

2:15 pm-8:10 pm

1 stop5h 55m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 10/23

6:44 pm-11:58 pm

1 stop5h 14m

Chicago O'Hare Intl

Sat 10/25

6:45 am-1:27 pm

1 stop6h 42m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 10/4

10:44 am-4:31 pm

1 stop5h 47m

Chicago O'Hare Intl

Wed 10/15

6:45 am-1:27 pm

1 stop6h 42m

$233

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sun 11/16

9:33 am-10:45 am

1 stop25h 12m

Chicago O'Hare Intl

Mon 11/24

11:42 am-6:49 pm

1 stop7h 07m

$239

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 11/28

6:25 pm-9:02 am

1 stop14h 37m

Chicago O'Hare Intl

Mon 12/1

9:18 am-6:49 pm

1 stop9h 31m

$260

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 1/7

10:16 am-3:26 pm

1 stop5h 10m

Chicago O'Hare Intl

Fri 1/9

5:00 am-11:27 am

1 stop6h 27m

$269

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 9/27

4:28 pm-9:45 pm

1 stop5h 17m

Chicago O'Hare Intl

Tue 9/30

1:20 pm-6:10 pm

1 stop4h 50m

$287

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Houston Hobby Airport averaging around $184.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $177. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Houston Hobby Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $246.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Houston Hobby Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $220 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $856. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Houston Hobby Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport from Houston Hobby Airport for as low as $147 on momondo.

How have Houston Hobby Airport to Chicago O'Hare Intl Airport flight prices changed over time?

As of September 2025, prices for Houston Hobby Airport to Chicago O'Hare Intl Airport flights are approximately 60% cheaper when compared to flights at the same time last year.

When to book flights from Houston Hobby Airport to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (HOU to ORD) flight deals and tips

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

Direct flights

None
There are no direct flights from Houston Hobby Airport to Chicago O'Hare Intl Airport. There are no popular flight routes from Houston Hobby Airport to Chicago O'Hare Intl Airport.
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  • How far is Houston Hobby to Chicago O'Hare Intl by plane?

    Houston Hobby and Chicago O'Hare Intl are 945.3 mi apart from one another. In terms of flight time, this usually takes a little over 4h 30m.

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

    Prices for flights from Houston Hobby Airport to Chicago O'Hare Intl Airport were last updated today.

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

  • How old do you have to be to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Houston Hobby Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Best airlines flying from Houston Hobby Airport to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Houston Hobby Airport to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $71Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
FrontierPriceFrom $76Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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South Haven
Rockford
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Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
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Janesville
Benton Harbor

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Houston to Chicago for you.

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

momondo does allow users to show only those flights to Chicago from Houston which offer a flexible booking policy as well as other useful filters and features.

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?

Yes momondo offers price alerts on flights to Chicago from Houston. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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