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Cheap flights from Houston Hobby Airport to Chicago from $119

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 4/21. 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
1 adult, Economy, 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
7:15 am - 12:50 pm
HOU
-
ORD
5h 35m
1 stop
Southwest Logo
11:55 am - 5:50 pm
ORD
-
HOU
5h 55m
1 stop
$200Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
6:00 am - 11:10 am
HOU
-
ORD
5h 10m
1 stop
Southwest Logo
10:30 am - 6:50 pm
ORD
-
HOU
8h 20m
2 stops
$205Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
6:00 am - 12:50 pm
HOU
-
ORD
6h 50m
2 stops
Southwest Logo
10:30 am - 6:50 pm
ORD
-
HOU
8h 20m
2 stops
$210Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
1:40 pm - 11:55 pm
HOU
-
ORD
10h 15m
1 stop
Southwest Logo
12:55 pm - 7:25 pm
ORD
-
HOU
6h 30m
1 stop
$228Southwest
Thu, May 7 - Sat, May 9
Southwest Logo
8:05 am - 6:50 pm
HOU
-
ORD
10h 45m
2 stops
Southwest Logo
7:00 am - 3:10 pm
ORD
-
HOU
8h 10m
1 stop
$233Southwest
Thu, May 7 - Sat, May 9
Delta Logo
5:23 pm - 11:58 pm
HOU
-
ORD
6h 35m
1 stop
Delta Logo
7:07 am - 12:11 pm
ORD
-
HOU
5h 04m
1 stop
$237Delta
Wed, May 6 - Wed, May 13
Southwest Logo
8:45 am - 6:50 pm
HOU
-
ORD
10h 05m
1 stop
Southwest Logo
3:45 pm - 9:55 pm
ORD
-
HOU
6h 10m
1 stop
$238Southwest
Wed, Apr 29 - Sun, May 3
Southwest Logo
6:00 am - 3:00 pm
HOU
-
ORD
9h 00m
2 stops
Southwest Logo
7:00 am - 3:10 pm
ORD
-
HOU
8h 10m
1 stop
$242Southwest
Tue, Apr 21 - Sat, Apr 25
Southwest Logo
7:00 am - 3:00 pm
HOU
-
ORD
8h 00m
2 stops
Southwest Logo
3:45 pm - 9:55 pm
ORD
-
HOU
6h 10m
1 stop
$244Southwest
Wed, Apr 29 - Sun, May 3
Southwest Logo
1:40 pm - 11:55 pm
HOU
-
ORD
10h 15m
1 stop
Southwest Logo
1:35 pm - 10:45 pm
ORD
-
HOU
9h 10m
1 stop
$245Southwest
Thu, Apr 16 - Tue, Apr 21

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
May 6
HOU5:23 pmHouston Hobby
6h 35m
1 stop
ORD11:58 pmChicago O'Hare Intl
May 13
ORD7:07 amChicago O'Hare Intl
5h 04m
1 stop
HOU12:11 pmHouston Hobby
$237
Delta
Apr 25
HOU10:48 amHouston Hobby
5h 54m
1 stop
ORD4:42 pmChicago O'Hare Intl
Apr 26
ORD5:15 amChicago O'Hare Intl
7h 25m
1 stop
HOU12:40 pmHouston Hobby
$257
Delta
May 20
HOU5:02 pmHouston Hobby
6h 57m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 27
ORD2:59 pmChicago O'Hare Intl
7h 27m
1 stop
HOU10:26 pmHouston Hobby
$266

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
May 18
HOU4:19 pmHouston Hobby
4h 55m
1 stop
ORD9:14 pmChicago O'Hare Intl
May 20
ORD10:41 amChicago O'Hare Intl
5h 08m
1 stop
HOU3:49 pmHouston Hobby
$296
American Airlines
Apr 1
HOU6:00 amHouston Hobby
5h 03m
1 stop
ORD11:03 amChicago O'Hare Intl
Apr 8
ORD10:41 amChicago O'Hare Intl
5h 07m
1 stop
HOU3:48 pmHouston Hobby
$326
American Airlines
Jun 9
HOU6:40 pmHouston Hobby
4h 57m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jun 16
ORD6:00 amChicago O'Hare Intl
6h 20m
1 stop
HOU12:20 pmHouston Hobby
$331

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 March 23, 2026.
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
Quickest round-trip

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 4/21

7:15 am-12:50 pm

1 stop5h 35m

Chicago O'Hare Intl

Tue 4/28

11:55 am-5:50 pm

1 stop5h 55m

$200

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 4/21

6:00 am-11:10 am

1 stop5h 10m

Chicago O'Hare Intl

Tue 4/28

10:30 am-6:50 pm

2 stops8h 20m

$205

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 4/21

6:00 am-12:50 pm

2 stops6h 50m

Chicago O'Hare Intl

Tue 4/28

10:30 am-6:50 pm

2 stops8h 20m

$210

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 5/7

1:40 pm-11:55 pm

1 stop10h 15m

Chicago O'Hare Intl

Sat 5/9

12:55 pm-7:25 pm

1 stop6h 30m

$228

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 5/7

8:05 am-6:50 pm

2 stops10h 45m

Chicago O'Hare Intl

Sat 5/9

7:00 am-3:10 pm

1 stop8h 10m

$233

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 5/6

5:23 pm-11:58 pm

1 stop6h 35m

Chicago O'Hare Intl

Wed 5/13

7:07 am-12:11 pm

1 stop5h 04m

$237

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 4/29

8:45 am-6:50 pm

1 stop10h 05m

Chicago O'Hare Intl

Sun 5/3

3:45 pm-9:55 pm

1 stop6h 10m

$238

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 4/21

6:00 am-3:00 pm

2 stops9h 00m

Chicago O'Hare Intl

Sat 4/25

7:00 am-3:10 pm

1 stop8h 10m

$242

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 4/29

7:00 am-3:00 pm

2 stops8h 00m

Chicago O'Hare Intl

Sun 5/3

3:45 pm-9:55 pm

1 stop6h 10m

$244

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 4/16

1:40 pm-11:55 pm

1 stop10h 15m

Chicago O'Hare Intl

Tue 4/21

1:35 pm-10:45 pm

1 stop9h 10m

$245

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 January 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 $228 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $768. 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 $213 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 $154 on momondo.

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

As of March 2026, prices for Houston Hobby Airport to Chicago O'Hare Intl Airport flights are approximately 37% 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

Fastest flight time

2h 35m

Direct flights

None
The fastest flight from Houston Hobby Airport to Chicago O'Hare Intl Airport takes 2h 35m
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

  • 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 35m.

  • 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 $63Free CancellationRating
5.7
3,020 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $72Free CancellationRating
6.3
8,532 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $148Free CancellationRating
7.4
9,459 reviews
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.1
11,485 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Rosemont
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Orland Park
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Joliet
Janesville
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Elgin
Tinley Park
South Holland

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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