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$59+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Dec 23 — Dec 301
Tue 12/23
Tue 12/30
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Houston Hobby to Chicago are usually found in February or October, booked 63 days in advance, depart on a Wednesday or Saturday 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 November 23, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

June

Cheapest in

February

Average price

$213

Good round-trip deal

$208 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Houston Hobby-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Houston Hobby-Chicago (CHI) flights.
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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. 11% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 23, 2025.

This Southwest deal was found by Cheapflights users on 11/22. 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.
Wed 12/312:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/68:55 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 11/22$117
This Southwest deal was found by Cheapflights users on 11/21. 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.
Sat 12/134:10 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 12/167:00 amMDW - HOU
Nonstop2h 40mSouthwest
Deal found 11/21$179
This Southwest deal was found by Cheapflights users on 11/22. 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.
Wed 12/246:35 amHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/68:55 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 11/22$188
This Southwest deal was found by Cheapflights users on 11/22. 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.
Wed 12/242:00 pmHOU - MDW
1 stop5h 35mSouthwest
Sun 1/115:55 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 11/22$198
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:40 pmHOU - MDW
1 stop5h 07mDelta
Tue 12/1610:49 amMDW - HOU
1 stop7h 03mDelta
Deal found 11/21$199
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:39 amHOU - ORD
1 stop4h 41mDelta
Tue 12/165:30 amORD - HOU
1 stop7h 58mDelta
Deal found 11/21$199
This Southwest deal was found by Cheapflights users on 11/21. 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.
Wed 12/242:00 pmHOU - MDW
1 stop5h 35mSouthwest
Wed 12/312:10 pmMDW - HOU
1 stop5h 25mSouthwest
Deal found 11/21$208
This Southwest deal was found by Cheapflights users on 11/21. 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.
Wed 12/1010:20 amHOU - MDW
Nonstop2h 25mSouthwest
Sat 12/137:30 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/21$214
This Southwest deal was found by Cheapflights users on 11/21. 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.
Fri 12/121:30 pmHOU - MDW
1 stop4h 15mSouthwest
Tue 12/165:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/21$218
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:47 pmHOU - ORD
1 stop5h 14mDelta
Tue 12/165:30 amORD - HOU
1 stop7h 58mDelta
Deal found 11/21$228
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amHOU - ORD
1 stop6h 03mDelta
Sat 12/134:20 pmORD - HOU
1 stop6h 13mDelta
Deal found 11/21$234
This Southwest deal was found by Cheapflights users on 11/21. 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.
Fri 12/125:55 amHOU - ORD
1 stop7h 35mSouthwest
Tue 12/161:45 pmORD - HOU
2 stops6h 05mSouthwest
Deal found 11/21$242

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 November 23, 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

Fri 1/23

5:04 pm-10:22 pm

1 stop5h 18m

Chicago Midway

Sat 1/31

4:30 pm-10:33 pm

1 stop6h 03m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 2/4

5:04 pm-11:56 pm

1 stop6h 52m

Chicago O'Hare Intl

Tue 2/10

11:15 am-4:10 pm

1 stop4h 55m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 1/13

5:04 pm-11:59 pm

1 stop6h 55m

Chicago O'Hare Intl

Tue 2/3

9:55 am-4:10 pm

1 stop6h 15m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 1/12

5:04 pm-11:59 pm

1 stop6h 55m

Chicago O'Hare Intl

Wed 2/4

9:55 am-4:10 pm

1 stop6h 15m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 1/23

5:04 pm-11:55 pm

1 stop6h 51m

Chicago O'Hare Intl

Sat 1/31

2:59 pm-10:33 pm

1 stop7h 34m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 1/23

5:04 pm-11:56 pm

1 stop6h 52m

Chicago O'Hare Intl

Tue 1/27

9:55 am-4:10 pm

1 stop6h 15m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 2/9

5:04 pm-11:56 pm

1 stop6h 52m

Chicago O'Hare Intl

Tue 2/10

11:15 am-4:10 pm

1 stop4h 55m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 12/16

6:00 am-12:10 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 12/16

4:20 pm-10:48 pm

1 stop6h 28m

$199

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 1/13

12:40 pm-10:35 pm

2 stops9h 55m

Chicago O'Hare Intl

Sun 1/18

11:55 am-7:50 pm

2 stops7h 55m

$206

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 1/14

12:40 pm-10:35 pm

2 stops9h 55m

Chicago O'Hare Intl

Sat 1/17

7:15 am-5:10 pm

2 stops9h 55m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 51 results
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Compare providers for flights from Hobby to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hobby to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Houston Hobby Airport-Chicago flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Houston Hobby Airport-Chicago flights, Cheapflights users trust Justfly.com the most. Justfly.com has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Houston Hobby Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 November 14, 2025.

Booking 63 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, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $53). Flying from Houston Hobby Airport to Chicago in April is currently the most expensive (average of $120). 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 November 23, 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 32% 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 November 2, 2025.

Travelers seeking maximum savings on their Houston Hobby Airport to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday 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?

How often are flights from Houston to Chicago delayed?

About 16% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 125 minutes.

What is the most punctual flight time for Houston to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Houston to Chicago flights?

Over the last year, Sun Country Air have had the lowest number of delays on this route, with no flights being classified as delayed.

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

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 November 23, 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
4,253 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
9,036 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
11,047 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
8,160 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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
3,100 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

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 $197, Southwest can have you in Chicago from Houston Hobby Airport in 5h 18m. 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 $77 on this airline. Additional options worth looking into are Frontier and Southwest, starting at $77 and $171 round-trip. Spirit Airlines is priced at 61% 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 Midway or Houston Hobby - Chicago Greater Rockford, Houston Hobby - Chicago O'Hare Intl 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, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $53). Flying from Houston Hobby Airport to Chicago in April is currently the most expensive (average of $120). 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
Lansing
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Porter
Benton Harbor
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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 November 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$172FlexibilityNo cancel feeOn-time65%
FrontierCheapest$77Average$182FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$171Average$281FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$177Average$341FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$177Average$262FlexibilityNo cancel feeOn-time71%

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