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$79+ Cheap flights from Hobby (HOU) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
ago. 23 — ago. 301
sáb. 8/23
sáb. 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago are usually found in September or October, booked 75 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Hobby to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated agosto 18, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

September

Average price

$196

Good round-trip deal

$208 or less

Good one-way deal

$188 or less
From Houston Hobby to Chicago (CHI)
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One-way flight from Houston Hobby to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Houston Hobby to Chicago (CHI).
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Price to beat on a one-way flight from Houston Hobby to Chicago (CHI).
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Find flight deals from Hobby to Chicago

Cheapest flights from Hobby to Chicago
Explore the most affordable flight options available from Hobby to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 18, 2025.

This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/161:25 pmHOU - MDW
Nonstop2h 25mSouthwest
mar. 9/235:25 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/17$157
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/208:20 pmHOU - MDW
Nonstop2h 25mSouthwest
lun. 9/228:45 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/18$177
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/197:00 pmHOU - MDW
1 stop4h 50mSouthwest
sáb. 9/204:30 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 8/18$187
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/18:55 pmHOU - MDW
Nonstop2h 25mSouthwest
dom. 10/510:55 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/17$188
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/199:45 pmHOU - MDW
Nonstop2h 20mSouthwest
lun. 9/228:45 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/17$197
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/175:50 pmHOU - MDW
1 stop4h 05mSouthwest
mié. 9/245:25 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/18$198
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/37:30 pmHOU - MDW
Nonstop2h 25mSouthwest
dom. 10/510:55 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/18$208
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/86:25 pmHOU - MDW
Nonstop2h 25mSouthwest
mié. 9/108:25 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/18$217
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/36:00 amHOU - ORD
1 stop4h 45mSouthwest
vie. 10/35:45 pmORD - HOU
1 stop4h 50mSouthwest
Deal found 8/17$217
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/511:30 amHOU - MDW
2 stops5h 30mSouthwest
vie. 11/75:10 amMDW - HOU
Nonstop2h 45mSouthwest
Deal found 8/16$219
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/206:20 amHOU - ORD
1 stop7h 45mSouthwest
lun. 9/2211:25 amORD - HOU
2 stops8h 50mSouthwest
Deal found 8/18$222
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/139:40 amHOU - MDW
1 stop6h 35mSouthwest
lun. 9/158:45 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/16$223

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby 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, Cheapflights users made 2,558,603 searches. Data last updated agosto 18, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago that are best for you.

Fly from

Hobby

Fly to

Chicago

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mar. 9/30

1:25 pm-3:50 pm

Nonstop2h 25m

Chicago Midway

mié. 10/1

9:10 am-11:45 am

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

sáb. 10/25

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

mar. 10/28

8:50 pm-11:25 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mar. 9/16

1:25 pm-3:50 pm

Nonstop2h 25m

Chicago Midway

mar. 9/23

5:25 pm-8:00 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mié. 10/22

9:15 pm-11:35 pm

Nonstop2h 20m

Chicago Midway

sáb. 10/25

12:15 pm-2:55 pm

Nonstop2h 40m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mié. 10/1

8:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

sáb. 10/4

5:35 pm-8:10 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mié. 9/17

4:45 pm-7:10 pm

Nonstop2h 25m

Chicago Midway

mié. 9/24

5:25 pm-8:00 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

dom. 10/5

9:00 am-11:25 am

Nonstop2h 25m

Chicago Midway

mié. 10/8

8:50 pm-11:25 pm

Nonstop2h 35m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mié. 9/24

11:25 am-1:55 pm

Nonstop2h 30m

Chicago Midway

dom. 9/28

6:00 am-8:30 am

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

vie. 10/3

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

mar. 10/7

8:50 pm-11:25 pm

Nonstop2h 35m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mié. 9/24

1:25 pm-3:50 pm

Nonstop2h 25m

Chicago Midway

jue. 9/25

5:45 am-8:15 am

Nonstop2h 30m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 41 results
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The best insider tips for Houston Hobby Airport to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Houston Hobby Airport to Chicago trip
Airports
HOU

HOU offers three types of parking: Valet, Garage, and Economy. Valet is convenient, located near the terminal entrance, saving time.

Read more about HOUby Scott Laird
MDW

The Orange Line train is the easiest way to reach downtown from MDW, taking less than 30 minutes to the city center.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Scott Laird

Scott Laird

Expert on HOU

Scott Laird

Scott Laird

Originally from Anchorage, Alaska, Scott is a frequent contributor to Fodor’s Travel Guide, Conde Nast Traveler, TravelAge West, and TravelPulse. He holds a Bachelor of Science in Organizational Management from Alaska Pacific University and a Master of Science in Airline Management from Embry-Riddle Aeronautical University, and has worked in the airline and hotel industries and as a travel consultant.

Read more

Best time to book a flight from Hobby to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hobby with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Houston Hobby Airport to Chicago

How far ahead should I book a flight from Houston Hobby Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Hobby to Chicago. Price data was last updated on August 8, 2025.

Booking 75 days in advance of your planned departure date is, on average, the best time to get cheap flights from Houston Hobby Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Houston Hobby Airport to Chicago?

Currently, August is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $245). Flying from Houston Hobby Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HOU to CHI?

Find hourly flight availability from Hobby to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 31% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Houston Hobby Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Hobby to Chicago. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Houston Hobby Airport to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Houston Hobby Airport to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated agosto 18, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Houston Hobby Airport to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Spirit Airlines
6.3
Okay
8,038 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
5.8
Fair
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Hobby to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Houston Hobby Airport to Chicago?

    For as low as $157, Southwest can have you in Chicago from Houston Hobby Airport in 2h 25m. Airlines will cover a distance of 938 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Houston Hobby Airport to Chicago round-trip?

    Our cheapest airline available from Houston Hobby Airport to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $64 on this airline. Additional options worth looking into are Frontier and American Airlines, starting at $69 and $169 round-trip. Spirit Airlines is priced at 67% lower than the current average price of a flight leaving 3 months from now.

  • What are the most popular routes from Houston Hobby Airport to Chicago?

    While some choose either Houston Hobby - Chicago O'Hare Intl or Houston Hobby - Chicago Greater Rockford, Houston Hobby - Chicago Midway is the most popular route from Houston Hobby Airport to Chicago.

  • Can I find deals for flights from Hobby to Chicago that include hotel bookings?

    Yes. In addition to deals on Hobby to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hobby to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hobby to Chicago.

  • Can I find deals for business class flights from Hobby to Chicago?

    Yes. Cheapflights offers flight deals from Hobby to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Houston Hobby Airport to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $245). Flying from Houston Hobby Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Lansing
Hammond
Benton Harbor
Porter
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Top 5 airlines flying from Hobby to Chicago

Discover the top 5 airlines that operate flights from Hobby to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$64Average$172FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$171FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$169Average$270FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$172Average$351FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$177Average$290FlexibilityNo cancel feeOn-time63%

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