HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$51+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hobby to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Houston Hobby to Chicago are usually found in September or April, booked 84 days in advance, depart on a Saturday 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$108
(Frontier)

One-way from

$51
(Frontier)
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
High demand for flights, 30% potential price rise
Search Deals
Best time to find cheap flights, 23% potential price drop
Search Deals
From Houston Hobby to Chicago (CHI)
Search Deals
One-way flight from Houston Hobby to Chicago (CHI)
Search Deals

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 20, 2024.

This Flightnetwork deal was found by Cheapflights users on 11/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:16 pmHOU - ORD
1 stop19h 44mFrontier
Wed 12/186:00 amORD - HOU
1 stop13h 09mFrontier
Deal found 11/19$126
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1310:36 amHOU - MDW
1 stop13h 37mFrontier
Sun 12/157:15 amMDW - HOU
1 stop26h 18mFrontier
Deal found 11/19$178
This Southwest deal was found by Cheapflights users on 11/20. 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 12/116:50 amHOU - MDW
Nonstop2h 25mSouthwest
Sat 12/147:55 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/20$220
This Delta deal was found by Cheapflights users on 11/20. 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 12/114:48 pmHOU - ORD
1 stop7h 10mDelta
Sun 12/155:40 amORD - HOU
1 stop6h 49mDelta
Deal found 11/20$236
This Delta deal was found by Cheapflights users on 11/20. 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 12/74:48 pmHOU - MDW
1 stop5h 18mDelta
Tue 12/106:00 amMDW - HOU
1 stop6h 29mDelta
Deal found 11/20$256
This KAYAK deal was found by Cheapflights users on 11/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:30 amHOU - ORD
1 stop10h 40mSouthwest
Fri 12/65:45 pmORD - HOU
2 stops13h 50mSouthwest
Deal found 11/19$271
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2610:14 amHOU - ORD
1 stop4h 38mAmerican Airlines
Tue 12/35:00 amORD - HOU
1 stop6h 53mAmerican Airlines
Deal found 11/19$306
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/258:47 amHOU - MDW
1 stop5h 37mAllegiant Air
Wed 11/2712:45 pmMDW - HOU
1 stop6h 53mAllegiant Air
Deal found 11/18$371
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2411:02 amHOU - MDW
1 stop6h 59mMultiple Airlines
Wed 11/2712:45 pmMDW - HOU
1 stop6h 53mMultiple Airlines
Deal found 11/18$395
This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/249:36 amHOU - ORD
1 stop7h 52mMultiple Airlines
Tue 11/266:00 amORD - HOU
1 stop7h 28mMultiple Airlines
Deal found 11/20$443
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/249:36 amHOU - ORD
1 stop7h 52mSun Country Air
Tue 11/2611:42 amORD - HOU
1 stop6h 37mSun Country Air
Deal found 11/19$446

Find flights from Hobby to Chicago within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 1/15

6:18 pm-12:13 am

1 stop5h 55m

Chicago Midway

Wed 1/22

8:15 am-5:26 pm

1 stop9h 11m

$108

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/11

6:16 pm-2:00 pm

1 stop19h 44m

Chicago O'Hare Intl

Wed 12/18

6:00 am-7:09 pm

1 stop13h 09m

$126

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 1/16

5:55 am-8:20 am

Nonstop2h 25m

Chicago Midway

Sun 1/19

8:40 pm-11:25 pm

Nonstop2h 45m

$198

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 1/21

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Sun 1/26

10:57 am-5:50 pm

1 stop6h 53m

$216

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 1/15

6:45 pm-11:59 pm

1 stop5h 14m

Chicago O'Hare Intl

Wed 1/22

5:15 pm-10:29 pm

1 stop5h 14m

$216

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 1/30

10:36 am-9:52 am

2 stops23h 16m

Chicago O'Hare Intl

Tue 2/4

1:39 pm-5:26 pm

2 stops27h 47m

$219

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/4

7:30 am-6:10 pm

1 stop10h 40m

Chicago O'Hare Intl

Fri 12/6

5:45 pm-7:35 am

2 stops13h 50m

$271

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 12/31

6:00 am-10:35 am

1 stop4h 35m

Chicago O'Hare Intl

Sun 1/12

5:00 am-9:45 am

1 stop4h 45m

$317

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/11

6:16 pm-12:13 am

1 stop5h 57m

$51

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 2/15

10:36 am-5:25 pm

1 stop6h 49m

$52

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 19 results
1
2

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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
FareScanPrice Accuracy3 starsTrust Score*1 star
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.

Travel insights for flights from Hobby to Chicago

Get recent, data-driven insights about flights from Hobby to Chicago including ideal travel times, pricing trends, and more.

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 15, 2024.

Booking 84 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, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $232). Flying from Houston Hobby Airport to Chicago in June is currently the most expensive (average of $308). 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 20, 2024.

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 24% on your trip compared to booking a flight at noon.

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 10, 2024.

Travelers seeking maximum savings on their Houston Hobby Airport to Chicago flight should consider departing on Saturday 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 20, 2024.
Peruse reviews from past customers who have flown with Frontier, American Airlines and Southwest from Houston to Chicago to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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.

  • 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 $108 on this airline. Additional options worth looking into are Southwest and Delta, starting at $198 and $216 round-trip. Frontier is priced at 43% 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 $51 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $107 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, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $232). Flying from Houston Hobby Airport to Chicago in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 6 airlines flying from Hobby to Chicago

Discover the top 6 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$146FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$158FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$138Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$153Average$248FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$190Average$384FlexibilityNo cancel feeOn-time63%
DeltaCheapest$237Average$575FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines