HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$89+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 28 days in advance, depart on a Wednesday or Friday 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 March 31, 2025.

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

March

Cheapest in

September

Average price

$231
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 31, 2025.

This Southwest deal was found by Cheapflights users on 3/30. 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 5/73:00 pmHOU - MDW
Nonstop2h 30mSouthwest
Wed 5/78:55 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 3/30$177
This Delta deal was found by Cheapflights users on 3/30. 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 5/310:13 amHOU - MDW
1 stop4h 35mDelta
Tue 5/134:15 pmMDW - HOU
1 stop5h 02mDelta
Deal found 3/30$217
This Delta deal was found by Cheapflights users on 3/30. 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 5/310:13 amHOU - ORD
1 stop6h 09mDelta
Tue 5/133:57 pmORD - HOU
1 stop5h 20mDelta
Deal found 3/30$217
This Southwest deal was found by Cheapflights users on 3/30. 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 5/17:55 amHOU - ORD
1 stop8h 30mSouthwest
Wed 5/71:30 pmORD - HOU
1 stop6h 10mSouthwest
Deal found 3/30$233
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/145:00 amHOU - ORD
1 stop6h 08mAmerican Airlines
Tue 5/206:45 pmORD - HOU
1 stop5h 13mAmerican Airlines
Deal found 3/31$269
This CheapOair deal was found by Cheapflights users on 3/30. 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.
Mon 4/710:36 amHOU - MDW
1 stop13h 45mFrontier
Tue 4/86:45 amMDW - HOU
1 stop26h 47mFrontier
Deal found 3/30$302
This CheapOair deal was found by Cheapflights users on 3/30. 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.
Mon 4/710:36 amHOU - ORD
1 stop14h 01mFrontier
Tue 4/86:45 amORD - HOU
1 stop26h 47mFrontier
Deal found 3/30$302
This Sun Country Air deal was found by Cheapflights users on 3/31. 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 6/56:30 pmHOU - ORD
1 stop17h 56mSun Country Air
Sun 6/86:30 amORD - HOU
1 stop11h 12mSun Country Air
Deal found 3/31$315
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Fri 5/3010:40 amHOU - ORD
2 stops26h 02mMultiple Airlines
Sun 6/17:00 amORD - HOU
1 stop10h 33mMultiple Airlines
Deal found 3/30$333
This eDestinos deal was found by Cheapflights users on 3/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1711:17 amHOU - MDW
1 stop22h 52mMultiple Airlines
Sun 4/206:45 amMDW - HOU
1 stop26h 47mMultiple Airlines
Deal found 3/31$335
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Fri 6/208:30 amHOU - MDW
1 stop5h 33mAllegiant Air
Mon 6/2310:34 amMDW - HOU
1 stop8h 37mAllegiant Air
Deal found 3/30$353

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 March 31, 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

Wed 5/7

3:00 pm-5:30 pm

Nonstop2h 30m

Chicago Midway

Wed 5/7

8:55 pm-11:40 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 5/3

10:13 am-2:48 pm

1 stop4h 35m

Chicago Midway

Tue 5/13

4:15 pm-9:17 pm

1 stop5h 02m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 5/3

10:13 am-4:22 pm

1 stop6h 09m

Chicago O'Hare Intl

Sat 5/10

7:05 am-12:17 pm

1 stop5h 12m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 5/1

7:55 am-4:25 pm

1 stop8h 30m

Chicago O'Hare Intl

Wed 5/7

1:30 pm-7:40 pm

1 stop6h 10m

$233

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 5/14

5:00 am-11:08 am

1 stop6h 08m

Chicago O'Hare Intl

Tue 5/20

6:45 pm-11:58 pm

1 stop5h 13m

$269

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 4/7

10:36 am-12:21 am

1 stop13h 45m

Chicago Midway

Tue 4/8

6:45 am-9:32 am

1 stop26h 47m

$302

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 6/5

6:30 pm-12:26 pm

1 stop17h 56m

Chicago O'Hare Intl

Sun 6/8

6:30 am-5:42 pm

1 stop11h 12m

$315

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 4/11

10:36 am-12:37 am

1 stop14h 01m

Chicago O'Hare Intl

Sun 4/13

6:45 am-9:32 am

1 stop26h 47m

$322

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 5/30

10:40 am-12:42 pm

2 stops26h 02m

Chicago O'Hare Intl

Sun 6/1

7:00 am-5:33 pm

1 stop10h 33m

$333

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 4/17

11:17 am-10:09 am

1 stop22h 52m

Chicago Midway

Sun 4/20

6:45 am-9:32 am

1 stop26h 47m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 24 results
1
2
3

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 March 28, 2025.

To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 28 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 $323). 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 March 31, 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 May 5, 2024.

Travelers seeking maximum savings on their Galveston to Chicago flight should consider departing on Wednesday 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 March 31, 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
9,818 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,275 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Allegiant Air
7.3
Good
731 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $89. However, be on the lookout for offers from Allegiant Air and Delta, 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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
Austin to O'Hare Intl flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hobby to Midway flights
San Antonio to O'Hare Intl flights
Love Field to Midway flights
Dallas/Fort Worth to St. Louis flights
Austin to Midway flights
Hobby to St. Louis flights
George Bush Intcntl to Midway flights
George Bush Intcntl to St. Louis flights
San Antonio to Midway flights
El Paso to O'Hare Intl flights
Love Field to St. Louis flights
Dallas/Fort Worth to Peoria flights
Austin to St. Louis flights
El Paso to Midway flights
San Antonio to St. Louis flights
Dallas/Fort Worth to Moline flights
McAllen to O'Hare Intl flights
Dallas/Fort Worth to Evansville flights
Hobby to Peoria flights
George Bush Intcntl to Peoria flights
Hobby to Moline flights
McAllen to Midway flights
El Paso to St. Louis flights
Lubbock to O'Hare Intl flights
Dallas/Fort Worth to Bloomington flights
George Bush Intcntl to Moline flights
Harlingen to O'Hare Intl flights
Love Field to Bloomington flights
Hobby to Evansville flights
George Bush Intcntl to Evansville flights
Austin to Moline flights
Corpus Christi to O'Hare Intl flights
Hobby to Decatur flights
Austin to Peoria flights
San Antonio to Peoria flights
Love Field to Evansville flights
Midland to O'Hare Intl flights
Brownsville to O'Hare Intl flights
Amarillo to O'Hare Intl flights
Corpus Christi to St. Louis flights
Dallas/Fort Worth to Springfield flights
Austin to Bloomington flights
San Antonio to Moline 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$51Average$142FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$60Average$148FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$145Average$245FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$146Average$338FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$195Average$361FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$406FlexibilityNo 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.