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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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago are usually found in September or February, booked 75 days in advance, depart on a Wednesday or Saturday 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 junio 12, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

September

Average price

$217

Good round-trip deal

$213 or less

Good one-way deal

$146 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. 5% potential increase in price ($10 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 June 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 junio 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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.
jue. 9/45:55 amHOU - MDW
Nonstop2h 25mSouthwest
lun. 9/85:45 amMDW - HOU
Nonstop2h 30mSouthwest
Deal found 6/10$157
This Southwest deal was found by Cheapflights users on 6/10. 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.
jue. 9/45:40 amHOU - ORD
1 stop7h 05mSouthwest
lun. 9/81:50 pmORD - HOU
1 stop7h 00mSouthwest
Deal found 6/10$177
This Delta deal was found by Cheapflights users on 6/10. 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.
mar. 8/269:57 amHOU - ORD
1 stop6h 31mDelta
mar. 9/25:45 amORD - HOU
1 stop6h 25mDelta
Deal found 6/10$217
This American Airlines deal was found by Cheapflights users on 6/12. 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.
mié. 8/206:30 pmHOU - ORD
1 stop5h 13mAmerican Airlines
lun. 8/2510:25 amORD - HOU
1 stop7h 35mAmerican Airlines
Deal found 6/12$251
This Delta deal was found by Cheapflights users on 6/12. 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.
vie. 8/14:16 pmHOU - MDW
1 stop5h 26mDelta
mar. 8/512:43 pmMDW - HOU
1 stop7h 57mDelta
Deal found 6/12$298
This Mytrip deal was found by Cheapflights users on 6/10. 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.
lun. 6/1610:39 amHOU - MDW
1 stop9h 07mAllegiant Air
lun. 6/3010:34 amMDW - HOU
1 stop8h 37mAllegiant Air
Deal found 6/10$341

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 junio 12, 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

jue. 9/4

5:55 am-8:20 am

Nonstop2h 25m

Chicago Midway

lun. 9/8

5:45 am-8:15 am

Nonstop2h 30m

$157

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

jue. 9/4

5:40 am-12:45 pm

1 stop7h 05m

Chicago O'Hare Intl

lun. 9/8

1:50 pm-8:50 pm

1 stop7h 00m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

mar. 8/26

9:57 am-4:28 pm

1 stop6h 31m

Chicago O'Hare Intl

mar. 9/2

5:45 am-12:10 pm

1 stop6h 25m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

mié. 8/20

6:30 pm-11:43 pm

1 stop5h 13m

Chicago O'Hare Intl

lun. 8/25

10:25 am-6:00 pm

1 stop7h 35m

$251

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

vie. 8/1

4:16 pm-9:42 pm

1 stop5h 26m

Chicago Midway

mar. 8/5

12:43 pm-8:40 pm

1 stop7h 57m

$298

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

lun. 6/16

10:39 am-7:46 pm

1 stop9h 07m

Chicago Midway

lun. 6/30

10:34 am-7:11 pm

1 stop8h 37m

$341

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

lun. 8/11

4:30 pm-6:55 pm

Nonstop2h 25m

$79

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

mié. 8/27

6:10 am-2:10 pm

1 stop8h 00m

$89

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mar. 7/22

6:00 am-11:58 am

1 stop5h 58m

$109

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

lun. 8/11

6:34 pm-11:56 pm

1 stop5h 22m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 17 results
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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 9, 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 junio 12, 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 31% on your trip compared to booking a flight in the afternoon.

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 8, 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. 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 junio 12, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 15% 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 Allegiant Air from $123 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$148FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$170FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$147Average$344FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$272FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$192Average$304FlexibilityNo cancel feeOn-time63%

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