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$62+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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The best prices from Houston Hobby to Chicago are usually found in September or April, booked 28 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(CheapOair)

One-way from

$65
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$187

Good round-trip deal

$274 or less

Good one-way deal

$198 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. 4% potential increase in price ($7 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 February 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 February 21, 2025.

This CheapOair deal was found by Cheapflights users on 2/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/210:36 amHOU - ORD
1 stop14h 06mFrontier
Thu 4/36:45 amORD - HOU
1 stop26h 47mFrontier
Deal found 2/20$140
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1110:36 amHOU - MDW
1 stop13h 45mFrontier
Sun 4/136:45 amMDW - HOU
1 stop26h 47mFrontier
Deal found 2/20$168
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 3/1310:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Mon 3/176:10 amMDW - HOU
Nonstop2h 50mSouthwest
Deal found 2/20$197
This Delta deal was found by Cheapflights users on 2/21. 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.
Tue 3/186:00 amHOU - ORD
1 stop7h 45mDelta
Tue 3/255:30 pmORD - HOU
1 stop5h 36mDelta
Deal found 2/21$217
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 3/187:55 amHOU - ORD
1 stop8h 30mSouthwest
Tue 3/256:00 amORD - HOU
2 stops10h 10mSouthwest
Deal found 2/20$222
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/76:00 amHOU - ORD
1 stop7h 06mAmerican Airlines
Wed 3/125:00 amORD - HOU
1 stop4h 38mAmerican Airlines
Deal found 2/21$292
This Sun Country Air deal was found by Cheapflights users on 2/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/172:59 pmHOU - ORD
1 stop28h 12mSun Country Air
Wed 7/238:10 pmORD - HOU
1 stop21h 26mSun Country Air
Deal found 2/20$295
This Delta deal was found by Cheapflights users on 2/21. 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.
Thu 4/1710:41 amHOU - MDW
1 stop7h 18mDelta
Sun 4/206:04 amMDW - HOU
1 stop6h 27mDelta
Deal found 2/21$398

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 2,558,603 searches. Data last updated February 21, 2025.

Fly from

Hobby

Fly to

Chicago

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 3/15

8:14 pm-12:17 am

1 stop28h 03m

Chicago Midway

Tue 4/1

6:40 am-9:32 am

1 stop26h 52m

$140

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 4/2

10:36 am-12:42 am

1 stop14h 06m

Chicago O'Hare Intl

Thu 4/3

6:45 am-9:32 am

1 stop26h 47m

$140

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 3/13

10:45 pm-1:10 am

Nonstop2h 25m

Chicago Midway

Mon 3/17

6:10 am-9:00 am

Nonstop2h 50m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 3/18

6:00 am-1:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 3/25

5:30 pm-11:06 pm

1 stop5h 36m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 3/18

7:55 am-4:25 pm

1 stop8h 30m

Chicago O'Hare Intl

Tue 3/25

6:00 am-4:10 pm

2 stops10h 10m

$222

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 3/7

6:00 am-1:06 pm

1 stop7h 06m

Chicago O'Hare Intl

Wed 3/12

5:00 am-9:38 am

1 stop4h 38m

$292

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 4/30

2:45 pm-10:26 pm

1 stop7h 41m

Chicago Midway

Sun 5/4

6:04 am-12:31 pm

1 stop6h 27m

$347

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 4/2

10:36 am-12:21 am

1 stop13h 45m

$62

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 3/26

10:36 am-12:44 am

1 stop14h 08m

$64

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 3/24

5:35 am-7:55 am

Nonstop2h 20m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February.
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*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.

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 February 14, 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 $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 February 21, 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 February 16, 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. Saturday 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 February 21, 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
4,406 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

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
4,406 reviews
Southwest
8.1
Very good
4,406 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

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

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,406 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

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
8,217 reviews
Southwest
8.1
Very good
4,406 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

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

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,406 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

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
4,406 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

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 $140 on this airline. Additional options worth looking into are Southwest and Delta, starting at $197 and $217 round-trip. Frontier is priced at 21% 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 $65 on Frontier. Other airlines that offer cheap prices include Southwest from $99 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 $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 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

Browse thousands of different options on Cheapflights for your next trip

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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 2,558,603 searches. Data last updated February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$143FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$157FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$143Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$250FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$395FlexibilityNo cancel feeOn-time63%
DeltaCheapest$317Average$490FlexibilityNo cancel feeOn-timeN/A
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