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$79+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago are usually found in February or September, booked 75 days in advance, depart on a Wednesday 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 July 3, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

February

Average price

$188

Good round-trip deal

$215 or less

Good one-way deal

$169 or less
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. 6% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/3. 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 10/16:35 amHOU - MDW
Nonstop2h 25mSouthwest
Wed 10/81:00 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 7/3$157
This Southwest deal was found by Cheapflights users on 7/3. 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 8/285:05 amHOU - ORD
1 stop6h 45mSouthwest
Tue 9/21:50 pmORD - HOU
1 stop6h 15mSouthwest
Deal found 7/3$177
This Delta deal was found by Cheapflights users on 7/2. 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 8/96:00 amHOU - MDW
1 stop5h 48mDelta
Tue 8/126:04 amMDW - HOU
1 stop6h 23mDelta
Deal found 7/2$217
This Delta deal was found by Cheapflights users on 7/3. 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 8/226:34 pmHOU - ORD
1 stop5h 22mDelta
Wed 9/177:20 amORD - HOU
1 stop4h 58mDelta
Deal found 7/3$217
This American Airlines deal was found by Cheapflights users on 7/2. 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 10/76:39 pmHOU - ORD
1 stop5h 03mAmerican Airlines
Tue 10/146:55 amORD - HOU
1 stop6h 59mAmerican Airlines
Deal found 7/2$251
This Sun Country Air deal was found by Cheapflights users on 7/3. 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 8/215:53 pmHOU - ORD
1 stop18h 39mSun Country Air
Thu 9/187:12 pmORD - HOU
1 stop14h 57mSun Country Air
Deal found 7/3$265
This Mytrip deal was found by Cheapflights users on 7/2. 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 8/79:42 amHOU - RFD
2 stops22h 10mAllegiant Air
Mon 8/118:42 amRFD - HOU
2 stops10h 31mAllegiant Air
Deal found 7/2$349

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 3, 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

Wed 10/1

6:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Wed 10/8

1:00 pm-3:35 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 8/28

6:10 am-2:25 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 9/2

1:50 pm-10:35 pm

1 stop8h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 8/9

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 8/12

6:04 am-12:27 pm

1 stop6h 23m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 8/22

6:34 pm-11:56 pm

1 stop5h 22m

Chicago O'Hare Intl

Tue 9/16

7:20 am-12:18 pm

1 stop4h 58m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/27

8:51 am-1:37 pm

1 stop4h 46m

Chicago O'Hare Intl

Sat 8/30

1:21 pm-6:00 pm

1 stop4h 39m

$251

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 8/21

5:53 pm-12:32 pm

1 stop18h 39m

Chicago O'Hare Intl

Thu 9/18

7:12 pm-10:09 am

1 stop14h 57m

$265

HoustonChicago

HOU - RFD

HOURFD

Houston Hobby

Thu 8/7

9:42 am-7:52 am

2 stops22h 10m

Chicago Greater Rockford

Mon 8/11

8:42 am-7:13 pm

2 stops10h 31m

$349

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 8/13

6:35 am-9:00 am

Nonstop2h 25m

$79

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 8/7

5:05 am-11:50 am

1 stop6h 45m

$89

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 8/7

6:00 am-11:48 am

1 stop5h 48m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 15 results
1
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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 June 27, 2025.

Booking 75 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 July 3, 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 33% 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 June 29, 2025.

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

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 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Allegiant Air 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
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
708 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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.
Sun Country Air
6.9
Okay
339 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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 $157 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $217 and $251 round-trip. Southwest is priced at 16% 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 $79 on Southwest. Other airlines that offer cheap prices include Delta from $109 and American Airlines from $126 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
Lansing
Benton Harbor
Porter
Hammond
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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$151FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$168FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$154Average$343FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$273FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$294FlexibilityNo cancel feeOn-time63%

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