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$59+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
1 adult, Economy
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Cheapflights Tip: The best prices from Galveston to Chicago are usually found in February or October, booked 63 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 November 18, 2025.

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

June

Cheapest in

February

Average price

$213
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($25 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 November 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 November 18, 2025.

This Southwest deal was found by Cheapflights users on 11/18. 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 12/242:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/66:15 amMDW - HOU
Nonstop3h 00mSouthwest
Deal found 11/18$117
This Southwest deal was found by Cheapflights users on 11/18. 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 12/242:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Wed 12/3112:00 pmMDW - HOU
1 stop5h 40mSouthwest
Deal found 11/18$127
This Southwest deal was found by Cheapflights users on 11/16. 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.
Mon 11/2411:00 amHOU - MDW
1 stop5h 30mSouthwest
Thu 11/276:10 amMDW - HOU
1 stop8h 15mSouthwest
Deal found 11/16$137
This Southwest deal was found by Cheapflights users on 11/16. 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 12/106:35 amHOU - MDW
Nonstop2h 25mSouthwest
Wed 12/1010:15 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 11/16$179
This Southwest deal was found by Cheapflights users on 11/17. 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.
Tue 12/3010:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/67:55 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/17$188
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:48 pmHOU - MDW
1 stop4h 52mDelta
Thu 11/275:34 pmMDW - HOU
1 stop5h 33mDelta
Deal found 11/17$197
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:46 amHOU - ORD
1 stop5h 35mDelta
Tue 1/62:50 pmORD - HOU
1 stop7h 43mDelta
Deal found 11/17$197
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amHOU - MDW
1 stop5h 55mDelta
Wed 12/1712:50 pmMDW - HOU
1 stop5h 02mDelta
Deal found 11/17$198
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amHOU - ORD
1 stop6h 03mDelta
Wed 12/179:49 amORD - HOU
1 stop8h 03mDelta
Deal found 11/17$198
This Delta deal was found by Cheapflights users on 11/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amHOU - MDW
1 stop5h 55mDelta
Wed 12/105:29 pmMDW - HOU
1 stop5h 19mDelta
Deal found 11/16$199
This Delta deal was found by Cheapflights users on 11/18. 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.
Wed 12/106:00 amHOU - ORD
1 stop6h 03mDelta
Sat 12/135:30 amORD - HOU
1 stop7h 58mDelta
Deal found 11/18$199
This Southwest deal was found by Cheapflights users on 11/16. 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.
Thu 12/1111:10 amHOU - MDW
1 stop5h 25mSouthwest
Tue 12/165:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/16$207

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 November 18, 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

Tue 2/3

5:45 am-11:59 am

1 stop6h 14m

Chicago Midway

Wed 2/4

10:46 am-4:10 pm

1 stop5h 24m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 1/27

5:04 pm-10:22 pm

1 stop5h 18m

Chicago Midway

Tue 2/3

10:48 am-4:10 pm

1 stop5h 22m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/10

6:00 am-12:03 pm

1 stop6h 03m

Chicago O'Hare Intl

Sat 12/13

5:30 am-1:28 pm

1 stop7h 58m

$199

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 12/13

10:39 am-3:20 pm

1 stop4h 41m

Chicago O'Hare Intl

Tue 12/16

4:20 pm-10:48 pm

1 stop6h 28m

$199

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 2/3

6:15 am-1:30 pm

1 stop7h 15m

Chicago O'Hare Intl

Wed 2/4

1:45 pm-9:40 pm

2 stops7h 55m

$224

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sun 12/7

10:39 am-4:45 pm

1 stop6h 06m

Chicago O'Hare Intl

Tue 12/9

11:15 am-5:52 pm

1 stop6h 37m

$228

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 12/7

7:25 pm-9:50 pm

Nonstop2h 25m

Chicago Midway

Sun 12/14

9:55 pm-12:35 am

Nonstop2h 40m

$237

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/3

2:35 pm-5:00 pm

Nonstop2h 25m

Chicago Midway

Thu 12/11

7:00 am-9:40 am

Nonstop2h 40m

$243

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/17

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Sat 12/20

8:35 pm-11:20 pm

Nonstop2h 45m

$248

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 12/11

12:50 pm-9:50 pm

1 stop9h 00m

Chicago O'Hare Intl

Sun 12/14

2:15 pm-7:10 pm

1 stop4h 55m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 49 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 November 14, 2025.

To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 63 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, January is the cheapest month in which you can book a flight from Galveston to Chicago (average of $53). Flying from Galveston to Chicago in May is currently the most expensive (average of $95). 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 November 18, 2025.

One of the essential ways to save on airfare from Galveston to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 49% on airfare.

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 Monday at noon when fares are most often at their lowest. Sunday 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 November 18, 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
4,248 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
9,019 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
11,045 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
8,151 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
3,105 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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?

    Delta and Southwest can get you from Galveston to Chicago in just under 6h 14m. Your travel time can differ by up to 1h 01m. There are 938 mi between Galveston and Chicago. This flight may include one or multiple stops.

  • 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, January is the cheapest month in which you can book a flight from Galveston to Chicago (average of $53). Flying from Galveston to Chicago in May is currently the most expensive (average of $95). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$170FlexibilityNo cancel feeOn-time65%
FrontierCheapest$77Average$186FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$160Average$265FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$171Average$281FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$177Average$348FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$346FlexibilityNo cancel feeOn-timeN/A

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