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Cheap flights from Houston Hobby Airport to Chicago from $98

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 2/28. 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

Enter your travel dates to find the best prices.
Delta Logo
10:50 am - 4:51 pm
HOU
-
ORD
6h 01m
1 stop
Delta Logo
2:46 pm - 10:28 pm
ORD
-
HOU
7h 42m
1 stop
$207Delta
Tue, Feb 24 - Wed, Mar 4
Delta Logo
10:46 am - 6:48 pm
HOU
-
ORD
8h 02m
1 stop
Delta Logo
9:50 am - 4:28 pm
ORD
-
HOU
6h 38m
1 stop
$211Delta
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
6:20 am - 2:45 pm
HOU
-
ORD
8h 25m
1 stop
Southwest Logo
3:05 pm - 8:15 pm
ORD
-
HOU
5h 10m
1 stop
$217Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
6:20 am - 3:25 pm
HOU
-
ORD
9h 05m
1 stop
Southwest Logo
11:55 am - 7:50 pm
ORD
-
HOU
7h 55m
2 stops
$222Southwest
Tue, Feb 24 - Wed, Mar 4
Southwest Logo
4:35 pm - 11:55 pm
HOU
-
ORD
7h 20m
1 stop
Southwest Logo
2:40 pm - 8:05 pm
ORD
-
HOU
5h 25m
1 stop
$225Southwest
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
6:55 am - 2:20 pm
HOU
-
ORD
7h 25m
1 stop
Southwest Logo
2:40 pm - 8:35 pm
ORD
-
HOU
5h 55m
2 stops
$230Southwest
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
6:30 am - 1:00 pm
HOU
-
ORD
6h 30m
1 stop
Southwest Logo
3:05 pm - 12:45 am
ORD
-
HOU
9h 40m
1 stop
$237Southwest
Wed, Mar 4 - Mon, Mar 9
Southwest Logo
8:55 pm - 9:45 am
HOU
-
ORD
12h 50m
1 stop
Southwest Logo
2:00 pm - 8:30 pm
ORD
-
HOU
6h 30m
1 stop
$241Southwest
Sat, Mar 14 - Wed, Mar 18
Southwest Logo
6:20 am - 3:25 pm
HOU
-
ORD
9h 05m
1 stop
Southwest Logo
1:45 pm - 9:40 pm
ORD
-
HOU
7h 55m
2 stops
$242Southwest
Tue, Feb 24 - Wed, Feb 25
Southwest Logo
6:15 am - 1:30 pm
HOU
-
ORD
7h 15m
1 stop
Southwest Logo
5:15 pm - 11:35 pm
ORD
-
HOU
6h 20m
1 stop
$247Southwest
Wed, Feb 18 - Sat, Feb 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
Feb 24
HOU10:50 amHouston Hobby
6h 01m
1 stop
ORD4:51 pmChicago O'Hare Intl
Mar 4
ORD2:46 pmChicago O'Hare Intl
7h 42m
1 stop
HOU10:28 pmHouston Hobby
$207
Delta
Apr 18
HOU10:46 amHouston Hobby
8h 02m
1 stop
ORD6:48 pmChicago O'Hare Intl
Apr 21
ORD9:50 amChicago O'Hare Intl
6h 38m
1 stop
HOU4:28 pmHouston Hobby
$211
Delta
May 5
HOU5:23 pmHouston Hobby
6h 36m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 9
ORD5:59 pmChicago O'Hare Intl
5h 09m
1 stop
HOU11:08 pmHouston Hobby
$249

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
Feb 14
HOU6:20 amHouston Hobby
8h 25m
1 stop
ORD2:45 pmChicago O'Hare Intl
Feb 21
ORD3:05 pmChicago O'Hare Intl
5h 10m
1 stop
HOU8:15 pmHouston Hobby
$217
Southwest
Feb 24
HOU6:20 amHouston Hobby
9h 05m
1 stop
ORD3:25 pmChicago O'Hare Intl
Mar 4
ORD11:55 amChicago O'Hare Intl
7h 55m
2 stops
HOU7:50 pmHouston Hobby
$222
Southwest
Mar 18
HOU4:35 pmHouston Hobby
7h 20m
1 stop
ORD11:55 pmChicago O'Hare Intl
Mar 25
ORD2:40 pmChicago O'Hare Intl
5h 25m
1 stop
HOU8:05 pmHouston Hobby
$225

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 February 3, 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

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 2/24

10:50 am-4:51 pm

1 stop6h 01m

Chicago O'Hare Intl

Wed 3/4

2:46 pm-10:28 pm

1 stop7h 42m

$207

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 4/18

10:46 am-6:48 pm

1 stop8h 02m

Chicago O'Hare Intl

Tue 4/21

9:50 am-4:28 pm

1 stop6h 38m

$211

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 2/14

6:20 am-2:45 pm

1 stop8h 25m

Chicago O'Hare Intl

Sat 2/21

3:05 pm-8:15 pm

1 stop5h 10m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 2/24

6:20 am-3:25 pm

1 stop9h 05m

Chicago O'Hare Intl

Wed 3/4

11:55 am-7:50 pm

2 stops7h 55m

$222

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 3/18

4:35 pm-11:55 pm

1 stop7h 20m

Chicago O'Hare Intl

Wed 3/25

2:40 pm-8:05 pm

1 stop5h 25m

$225

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 3/18

6:55 am-2:20 pm

1 stop7h 25m

Chicago O'Hare Intl

Wed 3/25

2:40 pm-8:35 pm

2 stops5h 55m

$230

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 3/4

6:30 am-1:00 pm

1 stop6h 30m

Chicago O'Hare Intl

Mon 3/9

3:05 pm-12:45 am

1 stop9h 40m

$237

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 3/14

8:55 pm-9:45 am

1 stop12h 50m

Chicago O'Hare Intl

Wed 3/18

2:00 pm-8:30 pm

1 stop6h 30m

$241

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 2/24

6:20 am-3:25 pm

1 stop9h 05m

Chicago O'Hare Intl

Wed 2/25

1:45 pm-9:40 pm

2 stops7h 55m

$242

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 2/18

6:15 am-1:30 pm

1 stop7h 15m

Chicago O'Hare Intl

Sat 2/21

5:15 pm-11:35 pm

1 stop6h 20m

$247

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 $215 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $812. 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 $211 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 $159 on momondo.

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

As of February 2026, prices for Houston Hobby Airport to Chicago O'Hare Intl Airport 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 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 $64Free CancellationRating
5.7
3,051 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $69Free CancellationRating
6.3
8,407 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.2
11,218 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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