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$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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Galveston to Chicago are usually found in October or February, booked 75 days in advance, depart on a Wednesday or Tuesday 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 septiembre 17, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

October

Average price

$190
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 17, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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.
sáb. 10/185:55 pmHOU - MDW
Nonstop2h 25mSouthwest
lun. 10/209:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/15$157
This Southwest deal was found by Cheapflights users on 9/17. 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.
sáb. 10/185:55 pmHOU - MDW
Nonstop2h 25mSouthwest
sáb. 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Deal found 9/17$163
This Southwest deal was found by Cheapflights users on 9/17. 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.
sáb. 11/84:10 pmHOU - MDW
Nonstop2h 25mSouthwest
lun. 11/172:10 pmMDW - HOU
1 stop5h 25mSouthwest
Deal found 9/17$167
This Southwest deal was found by Cheapflights users on 9/16. 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.
jue. 10/306:00 amHOU - MDW
2 stops5h 25mSouthwest
lun. 11/38:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 9/16$172
This Southwest deal was found by Cheapflights users on 9/16. 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.
sáb. 11/89:45 amHOU - MDW
1 stop5h 50mSouthwest
lun. 11/107:00 pmMDW - HOU
1 stop5h 30mSouthwest
Deal found 9/16$177
This Southwest deal was found by Cheapflights users on 9/15. 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.
lun. 10/205:40 amHOU - ORD
1 stop7h 05mSouthwest
sáb. 10/251:50 pmORD - HOU
1 stop6h 05mSouthwest
Deal found 9/15$177
This Southwest deal was found by Cheapflights users on 9/15. 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.
jue. 10/236:00 amHOU - MDW
2 stops5h 25mSouthwest
sáb. 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Deal found 9/15$178
This Southwest deal was found by Cheapflights users on 9/15. 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.
jue. 10/237:00 pmHOU - MDW
1 stop5h 05mSouthwest
dom. 10/266:45 amMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/15$187
This Southwest deal was found by Cheapflights users on 9/17. 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.
sáb. 10/181:50 pmHOU - ORD
2 stops8h 10mSouthwest
sáb. 10/257:30 amORD - HOU
2 stops9h 40mSouthwest
Deal found 9/17$187
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/45:55 pmHOU - MDW
Nonstop2h 25mSouthwest
sáb. 10/117:45 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/14$193
This Southwest deal was found by Cheapflights users on 9/16. 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.
jue. 10/1610:25 pmHOU - MDW
Nonstop2h 20mSouthwest
jue. 10/235:30 amMDW - HOU
Nonstop2h 30mSouthwest
Deal found 9/16$197
This Southwest deal was found by Cheapflights users on 9/16. 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.
mié. 10/2910:30 amHOU - ORD
1 stop4h 50mSouthwest
dom. 11/23:45 pmORD - HOU
1 stop6h 45mSouthwest
Deal found 9/16$197

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 septiembre 17, 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

sáb. 10/18

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

lun. 10/20

9:30 pm-12:05 am

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

lun. 10/20

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

lun. 10/27

9:30 pm-12:05 am

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mar. 11/11

11:05 am-4:50 pm

1 stop5h 45m

Chicago Midway

mar. 11/11

8:35 pm-11:20 pm

Nonstop2h 45m

$167

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

jue. 10/30

6:15 am-8:40 am

Nonstop2h 25m

Chicago Midway

lun. 11/3

8:15 am-1:55 pm

1 stop5h 40m

$167

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

sáb. 11/8

11:00 am-4:45 pm

1 stop5h 45m

Chicago Midway

mar. 11/18

10:50 am-3:15 pm

1 stop4h 25m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mar. 12/16

3:50 pm-8:15 pm

1 stop4h 25m

Chicago Midway

mar. 12/30

5:25 am-11:45 am

1 stop6h 20m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

dom. 10/26

10:10 pm-12:30 am

Nonstop2h 20m

Chicago Midway

jue. 10/30

5:30 am-8:00 am

Nonstop2h 30m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

sáb. 11/1

8:35 am-2:25 pm

1 stop5h 50m

Chicago O'Hare Intl

lun. 11/3

11:55 am-7:50 pm

1 stop7h 55m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

lun. 10/20

5:15 am-11:50 am

1 stop6h 35m

Chicago O'Hare Intl

lun. 10/27

4:20 pm-9:30 pm

1 stop5h 10m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

jue. 11/6

5:00 am-11:10 am

1 stop6h 10m

Chicago O'Hare Intl

lun. 11/10

3:45 pm-10:30 pm

1 stop6h 45m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 46 results
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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 September 12, 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 septiembre 17, 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 December 16, 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. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Galveston to Chicago?

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 septiembre 17, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines 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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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.
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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.
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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 Galveston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Galveston to Chicago?

    Southwest can get you from Galveston to Chicago in just under 2h 25m. Your travel time will be generally consistent. There are 938 mi between Galveston and Chicago. All flights are typically nonstop.

  • 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 Chicago?

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

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Alternative routes for Galveston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$71Average$169FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$179FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$160Average$267FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$177Average$354FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$177Average$284FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$331FlexibilityNo cancel feeOn-timeN/A

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