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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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Aug 31 — Sep 71
Sun 8/31
Sun 9/7
1 adult, Economy
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Cheapflights Tip: The best prices from Galveston to Chicago are usually found in September or October, 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 August 26, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

September

Average price

$197
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 26, 2025.

This Southwest deal was found by Cheapflights users on 8/25. 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 9/248:55 pmHOU - MDW
Nonstop2h 25mSouthwest
Wed 10/18:25 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/25$157
This Southwest deal was found by Cheapflights users on 8/26. 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 9/238:55 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 9/306:25 amMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/26$177
This Southwest deal was found by Cheapflights users on 8/24. 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 9/248:55 pmHOU - MDW
Nonstop2h 25mSouthwest
Sat 9/272:50 pmMDW - HOU
1 stop6h 25mSouthwest
Deal found 8/24$187
This Southwest deal was found by Cheapflights users on 8/26. 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 10/89:15 pmHOU - MDW
Nonstop2h 20mSouthwest
Wed 10/155:15 amMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/26$188
This Southwest deal was found by Cheapflights users on 8/25. 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 10/2310:25 pmHOU - MDW
Nonstop2h 20mSouthwest
Mon 10/279:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/25$197
This Southwest deal was found by Cheapflights users on 8/24. 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 9/306:35 amHOU - MDW
Nonstop2h 25mSouthwest
Fri 10/109:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/24$208
This Delta deal was found by Cheapflights users on 8/26. 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 9/236:00 amHOU - MDW
1 stop5h 48mDelta
Tue 9/3012:43 pmMDW - HOU
1 stop4h 57mDelta
Deal found 8/26$217
This Southwest deal was found by Cheapflights users on 8/26. 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.
Sat 10/185:30 amHOU - ORD
1 stop7h 35mSouthwest
Mon 10/205:45 pmORD - HOU
1 stop4h 50mSouthwest
Deal found 8/26$217
This Southwest deal was found by Cheapflights users on 8/24. 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.
Sat 10/43:10 pmHOU - MDW
1 stop3h 55mSouthwest
Mon 10/69:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/24$218
This Southwest deal was found by Cheapflights users on 8/25. 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 10/235:35 amHOU - ORD
1 stop8h 25mSouthwest
Mon 10/271:50 pmORD - HOU
2 stops7h 40mSouthwest
Deal found 8/25$222
This Southwest deal was found by Cheapflights users on 8/24. 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 10/248:00 amHOU - ORD
2 stops8h 45mSouthwest
Mon 10/271:50 pmORD - HOU
2 stops7h 40mSouthwest
Deal found 8/24$227
This Southwest deal was found by Cheapflights users on 8/25. 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 9/259:45 pmHOU - MDW
Nonstop2h 20mSouthwest
Sun 9/286:00 amMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/25$228

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 August 26, 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 9/24

8:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Sat 9/27

7:20 pm-9:50 pm

Nonstop2h 30m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 9/24

8:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 10/1

8:25 pm-10:55 pm

Nonstop2h 30m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 9/23

1:25 pm-3:50 pm

Nonstop2h 25m

Chicago Midway

Thu 9/25

7:45 am-10:15 am

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 9/29

5:55 am-8:20 am

Nonstop2h 25m

Chicago Midway

Wed 10/1

8:25 pm-10:55 pm

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 9/28

6:25 am-8:50 am

Nonstop2h 25m

Chicago Midway

Wed 10/1

8:25 pm-10:55 pm

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 9/25

9:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Sat 9/27

7:40 am-10:10 am

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 12/14

6:15 am-8:40 am

Nonstop2h 25m

Chicago Midway

Wed 12/17

7:00 am-9:40 am

Nonstop2h 40m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 11/14

9:50 pm-12:10 am

Nonstop2h 20m

Chicago Midway

Sat 11/15

7:30 pm-10:15 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 9/23

8:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Tue 9/30

6:25 am-8:55 am

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/4

9:45 am-12:05 pm

Nonstop2h 20m

Chicago Midway

Mon 10/6

9:30 pm-12:05 am

Nonstop2h 35m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

Showing 1-10 of 47 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 August 22, 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 August 26, 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 August 26, 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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
8,943 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
8,031 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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
3,200 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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 and Delta can get you from Galveston to Chicago in just under 2h 25m. Your travel time can differ by up to 3h 53m. There are 938 mi between Galveston and Chicago. This flight may include one or multiple stops.

  • 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 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 August 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$168FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$177FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$268FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$175Average$355FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$177Average$287FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$346FlexibilityNo cancel feeOn-timeN/A

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