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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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 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

$168 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 ($3 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 June 16, 2025.

This Southwest deal was found by Cheapflights users on 6/16. 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 8/271:25 pmHOU - MDW
Nonstop2h 25mSouthwest
Sat 8/304:30 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 6/16$157
This Delta deal was found by Cheapflights users on 6/14. 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 11/16:00 amHOU - ORD
1 stop6h 08mDelta
Tue 11/117:10 amORD - HOU
1 stop5h 02mDelta
Deal found 6/14$216
This Delta deal was found by Cheapflights users on 6/15. 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 58mDelta
Wed 8/2010:11 amMDW - HOU
1 stop7h 28mDelta
Deal found 6/15$217
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 9/125:40 amHOU - ORD
1 stop7h 05mSouthwest
Tue 9/167:00 amORD - HOU
1 stop7h 00mSouthwest
Deal found 6/15$217
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/168:23 pmHOU - ORD
1 stop4h 36mAmerican Airlines
Tue 7/226:20 pmORD - HOU
1 stop5h 30mAmerican Airlines
Deal found 6/15$259
This Mytrip deal was found by Cheapflights users on 6/15. 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 6/308:45 amHOU - MDW
1 stop5h 18mAllegiant Air
Fri 7/410:31 amMDW - HOU
1 stop8h 42mAllegiant Air
Deal found 6/15$310
This Sun Country Air deal was found by Cheapflights users on 6/14. 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.
Sun 6/296:18 pmHOU - ORD
1 stop22h 57mSun Country Air
Thu 7/36:09 pmORD - HOU
1 stop17h 27mSun Country Air
Deal found 6/14$385
This Mytrip deal was found by Cheapflights users on 6/15. 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 7/315:35 amHOU - MDW
2 stops30h 46mMultiple Airlines
Mon 8/41:11 pmMDW - HOU
1 stop6h 02mMultiple Airlines
Deal found 6/15$396
This Mytrip deal was found by Cheapflights users on 6/14. 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 6/299:38 amHOU - RFD
2 stops22h 17mAllegiant Air
Thu 7/312:44 pmRFD - HOU
2 stops29h 29mAllegiant Air
Deal found 6/14$537

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 June 16, 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 8/27

1:25 pm-3:50 pm

Nonstop2h 25m

Chicago Midway

Sat 8/30

4:30 pm-7:10 pm

Nonstop2h 40m

$157

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 11/1

6:00 am-12:08 pm

1 stop6h 08m

Chicago O'Hare Intl

Tue 11/11

7:10 am-12:12 pm

1 stop5h 02m

$216

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 8/9

6:00 am-11:58 am

1 stop5h 58m

Chicago Midway

Wed 8/20

10:11 am-5:39 pm

1 stop7h 28m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 9/12

5:40 am-12:45 pm

1 stop7h 05m

Chicago O'Hare Intl

Tue 9/16

7:00 am-2:00 pm

1 stop7h 00m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 7/16

8:23 pm-12:59 am

1 stop4h 36m

Chicago O'Hare Intl

Tue 7/22

6:20 pm-11:50 pm

1 stop5h 30m

$259

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 6/30

8:45 am-2:03 pm

1 stop5h 18m

Chicago Midway

Fri 7/4

10:31 am-7:13 pm

1 stop8h 42m

$310

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sun 6/29

6:18 pm-5:15 pm

1 stop22h 57m

Chicago O'Hare Intl

Thu 7/3

6:09 pm-11:36 am

1 stop17h 27m

$385

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 7/31

5:35 am-12:21 pm

2 stops30h 46m

Chicago Midway

Mon 8/4

1:11 pm-7:13 pm

1 stop6h 02m

$396

HoustonChicago

HOU - RFD

HOURFD

Houston Hobby

Sun 6/29

9:38 am-7:55 am

2 stops22h 17m

Chicago Greater Rockford

Thu 7/3

12:44 pm-6:13 pm

2 stops29h 29m

$537

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 9/30

11:25 am-1:55 pm

Nonstop2h 30m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 20 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 13, 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 June 16, 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 15, 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.

Weekly flight availability from Houston Hobby Airport to Chicago

Explore weekly flight availability from Hobby to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 16, 2025.

The most flights from HOU to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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 June 16, 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

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.8

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

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.8

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
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.8

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
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.8

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
722 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.8

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

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.1

Comfort

7.8

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 $216 and $259 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 $125 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$150FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$168FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$144Average$345FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$274FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$302FlexibilityNo cancel feeOn-time63%

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