HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$79+ Cheap flights from Galveston, TX 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
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Galveston to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Galveston 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 Galveston to Chicago

Keep the following information in mind while searching for Galveston to Chicago flight deals. Data was last updated June 12, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

September

Average price

$217
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Galveston to Chicago

Cheapest flights from Galveston to Chicago
Explore the most affordable flight options available from Galveston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 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.
Thu 9/45:55 amHOU - MDW
Nonstop2h 25mSouthwest
Mon 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.
Thu 9/45:40 amHOU - ORD
1 stop7h 05mSouthwest
Mon 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.
Tue 8/269:57 amHOU - ORD
1 stop6h 31mDelta
Tue 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.
Wed 8/206:30 pmHOU - ORD
1 stop5h 13mAmerican Airlines
Mon 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.
Fri 8/14:16 pmHOU - MDW
1 stop5h 26mDelta
Tue 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.
Mon 6/1610:39 amHOU - MDW
1 stop9h 07mAllegiant Air
Mon 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 Galveston 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 12, 2025.
Use the filters below to find and compare flights from Galveston to Chicago that are best for you.

Fly from

Galveston

Fly to

Chicago

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 9/4

5:55 am-8:20 am

Nonstop2h 25m

Chicago Midway

Mon 9/8

5:45 am-8:15 am

Nonstop2h 30m

$157

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 9/4

5:40 am-12:45 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 9/8

1:50 pm-8:50 pm

1 stop7h 00m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 8/26

9:57 am-4:28 pm

1 stop6h 31m

Chicago O'Hare Intl

Tue 9/2

5:45 am-12:10 pm

1 stop6h 25m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/20

6:30 pm-11:43 pm

1 stop5h 13m

Chicago O'Hare Intl

Mon 8/25

10:25 am-6:00 pm

1 stop7h 35m

$251

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 8/1

4:16 pm-9:42 pm

1 stop5h 26m

Chicago Midway

Tue 8/5

12:43 pm-8:40 pm

1 stop7h 57m

$298

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 6/16

10:39 am-7:46 pm

1 stop9h 07m

Chicago Midway

Mon 6/30

10:34 am-7:11 pm

1 stop8h 37m

$341

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 8/11

4:30 pm-6:55 pm

Nonstop2h 25m

$79

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/27

6:10 am-2:10 pm

1 stop8h 00m

$89

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 7/22

6:00 am-11:58 am

1 stop5h 58m

$109

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 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
1
2

Best time to book a flight from Galveston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Galveston 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 Galveston to Chicago

How far ahead should I book a flight from Galveston to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Galveston to Chicago. Price data was last updated on June 9, 2025.

To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 75 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Galveston to Chicago?

Currently, August is the cheapest month in which you can book a flight from Galveston to Chicago (average of $245). Flying from Galveston 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 G4L to CHI?

Find hourly flight availability from Galveston 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 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Galveston to Chicago as you normally would.

What is the cheapest day to fly from Galveston to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Galveston to Chicago. Price data was last updated on June 30, 2024.

Travelers seeking maximum savings on their Galveston 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 June 12, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Galveston to Chicago have to say. 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

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

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

Overall

8.0

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

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
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

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

Overall

8.0

Boarding

8.1

Entertainment

7.1

Crew

8.5

Food

7.1

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 Galveston 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 to fly from Galveston to Chicago one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from Delta and Allegiant Air, as they are both options that can get you from Galveston to Chicago for a low price.

  • What are the most popular routes from Galveston to Chicago?

    When deciding which route to take from Galveston to Chicago consider Houston Hobby - Chicago O'Hare Intl, Houston Hobby - Chicago Midway or Houston Hobby - Chicago Greater Rockford as they are the most popular.

  • Can I find deals for flights from Galveston to Chicago that include hotel bookings?

    Yes. In addition to deals on Galveston to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Galveston to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Galveston to Chicago.

  • Can I find deals for business class flights from Galveston to Chicago?

    Yes. Cheapflights offers flight deals from Galveston 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 Galveston to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Galveston to Chicago (average of $245). Flying from Galveston 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 Galveston?

Book flights to Galveston if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Galveston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Hobby to O'Hare Intl flights
Hobby to Midway flights
Austin to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Love Field to O'Hare Intl flights
San Antonio to O'Hare Intl flights
Love Field to Midway flights
Dallas/Fort Worth to St. Louis flights
Austin to Midway flights
George Bush Intcntl to Midway flights
Hobby to St. Louis flights
El Paso to O'Hare Intl flights
San Antonio to Midway flights
George Bush Intcntl to St. Louis flights
Love Field to St. Louis flights
Austin to St. Louis flights
El Paso to Midway flights
McAllen to O'Hare Intl flights
Dallas/Fort Worth to Peoria flights
San Antonio to St. Louis flights
Austin to Rockford flights
Dallas/Fort Worth to Moline flights
Harlingen to O'Hare Intl flights
Hobby to Bloomington flights
Hobby to Peoria flights
El Paso to St. Louis flights
Dallas/Fort Worth to Evansville flights
George Bush Intcntl to Peoria flights
Lubbock to O'Hare Intl flights
Hobby to Moline flights
Hobby to Decatur flights
San Antonio to Peoria flights
Hobby to Springfield flights
George Bush Intcntl to Bloomington flights
Austin to Moline flights
George Bush Intcntl to Moline flights
George Bush Intcntl to Springfield flights
McAllen to Midway flights
Brownsville to O'Hare Intl flights
Corpus Christi to O'Hare Intl flights
Dallas/Fort Worth to Bloomington flights
Austin to Peoria flights
Austin to Bloomington flights
Midland to O'Hare Intl flights
Love Field to Moline flights
Laredo to O'Hare Intl flights
Dallas/Fort Worth to Springfield flights

Top 6 airlines flying from Galveston to Chicago

Discover the top 6 airlines that operate flights from Galveston 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$152FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$162FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$141Average$260FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$347FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$192Average$304FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$346FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights