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$105+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago are usually found in January or October, booked 85 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap 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 July 16, 2026.

This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 8/205:00 am
HOU
-
MDW
Nonstop2h 25m
Southwest
Tue 8/258:25 pm
MDW
-
HOU
Nonstop2h 25m
Southwest
Deal found 7/13$209
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 8/132:20 pm
HOU
-
MDW
Nonstop2h 20m
Southwest
Mon 8/171:05 pm
MDW
-
HOU
1 stop5h 20m
Southwest
Deal found 7/13$215
This Southwest deal was found by Cheapflights users on 7/13. 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 8/87:40 pm
HOU
-
MDW
Nonstop2h 20m
Southwest
Tue 8/117:50 am
MDW
-
HOU
Nonstop2h 35m
Southwest
Deal found 7/13$217
This Southwest deal was found by Cheapflights users on 7/13. 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 8/226:00 am
HOU
-
MDW
1 stop5h 50m
Southwest
Tue 8/252:05 pm
MDW
-
HOU
Nonstop2h 30m
Southwest
Deal found 7/13$219
This Southwest deal was found by Cheapflights users on 7/13. 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 9/911:25 am
HOU
-
MDW
1 stop4h 05m
Southwest
Thu 9/1010:05 am
MDW
-
HOU
1 stop3h 50m
Southwest
Deal found 7/13$220
This Southwest deal was found by Cheapflights users on 7/11. 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.
Thu 8/2711:30 am
HOU
-
MDW
2 stops5h 25m
Southwest
Mon 8/311:05 pm
MDW
-
HOU
1 stop5h 20m
Southwest
Deal found 7/11$225
This Southwest deal was found by Cheapflights users on 7/15. 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 8/158:10 am
HOU
-
MDW
1 stop5h 55m
Southwest
Sat 8/2210:25 am
MDW
-
HOU
Nonstop2h 30m
Southwest
Deal found 7/15$227
This Delta deal was found by Cheapflights users on 7/13. 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.
Tue 8/45:20 pm
HOU
-
MDW
1 stop5h 16m
Delta
Tue 8/116:05 am
MDW
-
HOU
1 stop6h 11m
Delta
Deal found 7/13$229
This Delta deal was found by Cheapflights users on 7/13. 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.
Thu 8/205:20 pm
HOU
-
ORD
1 stop6h 37m
Delta
Thu 8/273:25 pm
ORD
-
HOU
1 stop6h 40m
Delta
Deal found 7/13$229
This Delta deal was found by Cheapflights users on 7/13. 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 8/225:20 pm
HOU
-
MDW
1 stop5h 16m
Delta
Mon 8/241:25 pm
MDW
-
HOU
2 stops8h 40m
Delta
Deal found 7/13$234
This Delta deal was found by Cheapflights users on 7/13. 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.
Thu 8/205:20 pm
HOU
-
ORD
1 stop6h 37m
Delta
Tue 8/256:59 am
ORD
-
HOU
2 stops9h 26m
Delta
Deal found 7/13$234
This Southwest deal was found by Cheapflights users on 7/13. 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.
Mon 8/2411:30 am
HOU
-
MDW
2 stops5h 25m
Southwest
Tue 8/257:40 am
MDW
-
HOU
2 stops6h 05m
Southwest
Deal found 7/13$235

Find 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 July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Southwest)

One-way from

$105
(Southwest)

Popular in

May

Cheapest in

January

Average price

$284

Good round-trip deal

$349 or less

Good one-way deal

$211 or less
Provider with most accurate pricing for Houston Hobby-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Houston Hobby-Chicago (CHI) flights.
Search Deals
From Houston Hobby to Chicago (CHI)
Search Deals
One-way flight from Houston Hobby to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Houston Hobby to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Houston Hobby to Chicago (CHI).
Search Deals

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 July 16, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 8/26

8:50 pm-11:10 pm

Nonstop2h 20m

Chicago Midway

Wed 9/2

7:50 am-10:25 am

Nonstop2h 35m

$209

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 9/9

11:25 am-3:30 pm

1 stop4h 05m

Chicago Midway

Thu 9/10

10:05 am-12:35 pm

Nonstop2h 30m

$215

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 8/26

5:20 pm-10:36 pm

1 stop5h 16m

Chicago Midway

Tue 9/1

6:05 am-12:16 pm

1 stop6h 11m

$229

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 8/17

5:20 pm-11:57 pm

1 stop6h 37m

Chicago O'Hare Intl

Thu 8/20

1:50 pm-10:05 pm

1 stop8h 15m

$229

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 8/29

5:20 pm-11:57 pm

1 stop6h 37m

Chicago O'Hare Intl

Sat 9/5

3:25 pm-9:23 pm

1 stop5h 58m

$229

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 9/10

5:26 pm-11:59 pm

1 stop6h 33m

Chicago O'Hare Intl

Mon 9/14

11:29 am-4:31 pm

1 stop5h 02m

$229

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 9/12

5:26 pm-11:59 pm

1 stop6h 33m

Chicago O'Hare Intl

Mon 9/14

9:45 am-4:31 pm

1 stop6h 46m

$229

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/26

1:13 pm-6:49 pm

1 stop5h 36m

Chicago O'Hare Intl

Sat 8/29

6:59 am-4:25 pm

2 stops9h 26m

$234

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 8/11

1:13 pm-8:55 pm

1 stop7h 42m

Chicago O'Hare Intl

Tue 8/18

11:22 am-10:05 pm

2 stops10h 43m

$234

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 8/12

2:35 pm-8:10 pm

2 stops5h 35m

Chicago Midway

Tue 8/18

2:40 pm-7:55 pm

2 stops5h 15m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/13

Showing 1-10 of 50 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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

Currently, February is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $29). Flying from Houston Hobby Airport to Chicago in August is currently the most expensive (average of $589). 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 July 16, 2026.

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 29% on your trip compared to booking a flight at noon.

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 22% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 117 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 early afternoon 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 Sunday 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, Southwest have had the lowest number of delays on this route, with just 22% of flights being delayed.

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

Booking 78 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 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 July 11, 2026.

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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Houston Hobby Airport to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Houston Hobby Airport to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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

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 July 16, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Delta
7.8
Good
8,471 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
United Airlines
7.4
Good
9,993 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
American Airlines
7.1
Good
11,814 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.6
Fair
2,797 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 $209, Southwest can have you in Chicago from Houston Hobby Airport in 2h 20m. 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 Frontier. Our recent data shows that you can find tickets from as low as $62 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $158 and $177 round-trip. Frontier is priced at 72% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Houston Hobby Airport to Chicago one-way?

    One-way options have recently been found by users for as low as $29 on Frontier. Other airlines that offer cheap prices include American Airlines from $80 and Southwest from $89 one-way.

  • 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, February is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $29). Flying from Houston Hobby Airport to Chicago in August is currently the most expensive (average of $589). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 4 airlines flying from Hobby to Chicago

Discover the top 4 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 July 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$192FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$158Average$361FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$177Average$371FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$177Average$279FlexibilityNo cancel feeOn-time71%

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