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$89+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago are usually found in September or April, booked 28 days in advance, depart on a Wednesday or Friday 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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

March

Cheapest in

September

Average price

$231

Good round-trip deal

$298 or less

Good one-way deal

$174 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. 2% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 26, 2025.

This Southwest deal was found by Cheapflights users on 3/25. 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 5/39:00 pmHOU - MDW
Nonstop2h 30mSouthwest
Tue 5/68:45 amMDW - HOU
Nonstop2h 45mSouthwest
Deal found 3/25$177
This Delta deal was found by Cheapflights users on 3/24. 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 4/234:00 pmHOU - ORD
1 stop4h 50mDelta
Wed 4/3011:15 amORD - HOU
1 stop6h 26mDelta
Deal found 3/24$217
This Delta deal was found by Cheapflights users on 3/25. 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 6/710:22 amHOU - MDW
1 stop4h 58mDelta
Tue 6/106:00 amMDW - HOU
1 stop6h 07mDelta
Deal found 3/25$228
This Southwest deal was found by Cheapflights users on 3/25. 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 5/76:00 amHOU - ORD
1 stop4h 45mSouthwest
Sat 5/101:50 pmORD - HOU
1 stop6h 00mSouthwest
Deal found 3/25$228
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 7/165:00 amHOU - ORD
1 stop5h 04mAmerican Airlines
Wed 7/235:00 amORD - HOU
1 stop4h 40mAmerican Airlines
Deal found 3/25$257
This CheapOair deal was found by Cheapflights users on 3/25. 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.
Sat 4/512:27 pmHOU - MDW
1 stop11h 54mFrontier
Tue 4/86:45 amMDW - HOU
1 stop26h 47mFrontier
Deal found 3/25$282
This Sun Country Air deal was found by Cheapflights users on 3/25. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:30 pmHOU - ORD
1 stop17h 57mSun Country Air
Sun 6/17:00 amORD - HOU
1 stop10h 39mSun Country Air
Deal found 3/25$300
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Thu 4/2411:17 amHOU - MDW
1 stop22h 52mAllegiant Air
Sun 4/2710:08 amMDW - HOU
2 stops22h 21mAllegiant Air
Deal found 3/25$351
This CheapOair deal was found by Cheapflights users on 3/25. 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.
Wed 3/2610:36 amHOU - ORD
1 stop14h 08mFrontier
Sun 3/306:50 amORD - HOU
1 stop26h 46mFrontier
Deal found 3/25$352

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 March 26, 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

Sat 5/3

9:00 pm-11:30 pm

Nonstop2h 30m

Chicago Midway

Tue 5/6

8:45 am-11:30 am

Nonstop2h 45m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 4/23

4:00 pm-8:50 pm

1 stop4h 50m

Chicago O'Hare Intl

Wed 4/30

11:15 am-5:41 pm

1 stop6h 26m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 6/7

10:22 am-3:20 pm

1 stop4h 58m

Chicago Midway

Tue 6/10

6:00 am-12:07 pm

1 stop6h 07m

$228

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 5/7

6:00 am-10:45 am

1 stop4h 45m

Chicago O'Hare Intl

Sat 5/10

1:50 pm-7:50 pm

1 stop6h 00m

$228

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 7/16

5:00 am-10:04 am

1 stop5h 04m

Chicago O'Hare Intl

Wed 7/23

5:00 am-9:40 am

1 stop4h 40m

$257

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 4/5

12:27 pm-12:21 am

1 stop11h 54m

Chicago Midway

Tue 4/8

6:45 am-9:32 am

1 stop26h 47m

$282

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 5/29

6:30 pm-12:27 pm

1 stop17h 57m

Chicago O'Hare Intl

Sun 6/1

7:00 am-5:39 pm

1 stop10h 39m

$300

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 4/24

11:17 am-10:09 am

1 stop22h 52m

Chicago Midway

Sun 4/27

10:08 am-8:29 am

2 stops22h 21m

$351

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 4/26

9:00 pm-11:30 pm

Nonstop2h 30m

$89

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 6/6

10:39 am-7:46 pm

1 stop9h 07m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 20 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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
FareScanPrice Accuracy-Trust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 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 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

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 March 21, 2025.

Booking 28 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 $323). 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 March 26, 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 39% 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 March 23, 2025.

Travelers seeking maximum savings on their Houston Hobby Airport to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons 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 March 26, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Delta 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
4,274 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
Alaska Airlines
8.0
Very good
9,789 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
Allegiant Air
7.3
Good
730 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

  • 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 Southwest. Our recent data shows that you can find tickets from as low as $177 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $217 and $257 round-trip.

  • 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 $89 on Southwest. Other airlines that offer cheap prices include Allegiant Air from $103 and Delta from $109 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, 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 $323). 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 Houston Hobby Airport?

Book flights to Houston Hobby Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$52Average$141FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$60Average$154FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$154Average$343FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$248FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$195Average$361FlexibilityNo cancel feeOn-time63%
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