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Cheap flights from Houston Hobby Airport to Chicago from $104

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Houston Hobby Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:28 pm - 11:57 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:30 am - 2:07 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
7h 37m1 stop Atlanta Hartsfield-Jackson
$229Delta
Tue, Oct 13 - Tue, Oct 20
Delta Logo
3:09 pm - 8:38 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:40 pm - 11:03 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
7h 23m1 stop Atlanta Hartsfield-Jackson
$229Delta
Wed, Oct 21 - Mon, Oct 26
Delta Logo
2:25 pm - 8:56 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:40 am - 1:18 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
6h 38m1 stop Atlanta Hartsfield-Jackson
$229Delta
Tue, Sep 15 - Wed, Sep 16
Delta Logo
5:26 pm - 11:59 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:40 pm - 10:39 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
6h 59m1 stop Atlanta Hartsfield-Jackson
$229Delta
Wed, Sep 16 - Wed, Sep 30
Delta Logo
5:26 pm - 11:59 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 1:18 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
7h 48m1 stop Atlanta Hartsfield-Jackson
$229Delta
Wed, Sep 23 - Thu, Sep 24
Delta Logo
2:25 pm - 8:56 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:05 am - 1:18 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
5h 13m1 stop Atlanta Hartsfield-Jackson
$229Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
11:12 am - 4:58 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 46m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:15 pm - 11:03 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
7h 48m1 stop Atlanta Hartsfield-Jackson
$229Delta
Wed, Oct 7 - Sat, Oct 10
Delta Logo
5:26 pm - 11:59 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:40 pm - 10:39 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
6h 59m1 stop Atlanta Hartsfield-Jackson
$229Delta
Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
6:19 pm - 12:14 amHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 55m1 stop Dallas/Fort Worth
American Airlines Logo
3:00 pm - 7:48 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
4h 48m1 stop Dallas/Fort Worth
$255American Airlines
Fri, Sep 25 - Sat, Sep 26
American Airlines Logo
6:19 pm - 11:30 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 11m1 stop Dallas/Fort Worth
American Airlines Logo
3:00 pm - 7:48 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
4h 48m1 stop Dallas/Fort Worth
$255American Airlines
Thu, Sep 24 - Fri, Sep 25

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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
Sep 24
HOU6:19 pmHouston Hobby
5h 55m
1 stop
ORD12:14 amChicago O'Hare Intl
Oct 1
ORD11:00 amChicago O'Hare Intl
4h 43m
1 stop
HOU3:43 pmHouston Hobby
$255
American Airlines
Oct 6
HOU6:00 amHouston Hobby
5h 09m
1 stop
ORD11:09 amChicago O'Hare Intl
Oct 13
ORD6:02 pmChicago O'Hare Intl
5h 47m
1 stop
HOU11:49 pmHouston Hobby
$267
American Airlines
Oct 10
HOU5:06 pmHouston Hobby
5h 04m
1 stop
ORD10:10 pmChicago O'Hare Intl
Oct 17
ORD6:00 amChicago O'Hare Intl
5h 11m
1 stop
HOU11:11 amHouston Hobby
$273

Delta flights from Houston Hobby Airport to Chicago O'Hare Intl Airport

Our best Delta deals on Houston Hobby Airport to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 16
HOU5:26 pmHouston Hobby
6h 33m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 30
ORD3:40 pmChicago O'Hare Intl
6h 59m
1 stop
HOU10:39 pmHouston Hobby
$229
Delta
Oct 7
HOU3:09 pmHouston Hobby
5h 29m
1 stop
ORD8:38 pmChicago O'Hare Intl
Oct 10
ORD11:09 amChicago O'Hare Intl
11h 54m
2 stops
HOU11:03 pmHouston Hobby
$234
Delta
Oct 7
HOU11:12 amHouston Hobby
9h 18m
2 stops
ORD8:30 pmChicago O'Hare Intl
Oct 10
ORD1:55 pmChicago O'Hare Intl
9h 08m
2 stops
HOU11:03 pmHouston Hobby
$239

momondo Fare Finder

 
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

Cheapest round-trip

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Tue 10/13

5:28 pm-11:57 pm

1 stop6h 29m

Chicago O'Hare Intl

Tue 10/20

6:30 am-2:07 pm

1 stop7h 37m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Wed 10/21

3:09 pm-8:38 pm

1 stop5h 29m

Chicago O'Hare Intl

Mon 10/26

3:40 pm-11:03 pm

1 stop7h 23m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Tue 9/15

2:25 pm-8:56 pm

1 stop6h 31m

Chicago O'Hare Intl

Wed 9/16

6:40 am-1:18 pm

1 stop6h 38m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Wed 9/16

5:26 pm-11:59 pm

1 stop6h 33m

Chicago O'Hare Intl

Wed 9/30

3:40 pm-10:39 pm

1 stop6h 59m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Wed 9/23

5:26 pm-11:59 pm

1 stop6h 33m

Chicago O'Hare Intl

Thu 9/24

5:30 am-1:18 pm

1 stop7h 48m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Tue 9/22

2:25 pm-8:56 pm

1 stop6h 31m

Chicago O'Hare Intl

Tue 9/29

8:05 am-1:18 pm

1 stop5h 13m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Wed 10/7

11:12 am-4:58 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 10/10

3:15 pm-11:03 pm

1 stop7h 48m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Wed 9/16

5:26 pm-11:59 pm

1 stop6h 33m

Chicago O'Hare Intl

Sat 9/19

3:40 pm-10:39 pm

1 stop6h 59m

$229

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Fri 9/25

6:19 pm-12:14 am

1 stop5h 55m

Chicago O'Hare Intl

Sat 9/26

3:00 pm-7:48 pm

1 stop4h 48m

$255
Quickest round-trip

HoustonChicago

HOU Houston Hobby - ORD Chicago O'Hare Intl

HOUORD

Houston Hobby

Thu 9/24

6:19 pm-11:30 pm

1 stop5h 11m

Chicago O'Hare Intl

Fri 9/25

3:00 pm-7:48 pm

1 stop4h 48m

$255

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 typical price of a round-trip flight between Houston Hobby Airport and Chicago O'Hare Intl Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $162 to $307.
The lowest price recently found on this route was $229.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Houston Hobby Airport averaging around $177.

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 $242 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $804. 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 from Houston Hobby Airport 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 $246 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 $190 on momondo.

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

As of August 2026, prices for Houston Hobby Airport to Chicago O'Hare Intl Airport flights are approximately 54% more expensive 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

Best Price Found

$104

Fastest flight time

2h 30m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Houston Hobby Airport in the past 72 hours is $104. The best round-trip flight deal from Houston Hobby Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $229.
The fastest flight from Houston Hobby Airport to Chicago O'Hare Intl Airport takes 2h 30m
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.
Search flight deals

Frequently asked questions about flying from Houston Hobby Airport to Chicago O'Hare Intl Airport

  • 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 2h 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
FrontierPriceFrom $64Free CancellationRating
5.6
2,645 reviews
Search Frontier flights
United AirlinesPriceFrom $158Free CancellationRating
7.4
10,128 reviews
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.1
12,009 reviews
Search American Airlines flights
JetBluePriceFrom $268Free CancellationRating
7.1
3,038 reviews
Search JetBlue flights

Traveling to a place near Chicago?

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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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