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Galveston

$66+ Cheap flights from Chicago (CHI) to Galveston, TX

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Galveston are usually found in January or September, booked 73 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Chicago to Galveston

Cheapest flights from Chicago to Galveston
Explore the most affordable flight options available from Chicago to Galveston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Southwest deal was found by Cheapflights users on 12/20. 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 12/3112:00 pmMDW - HOU
1 stop5h 40mSouthwest
Thu 1/15:40 amHOU - MDW
1 stop5h 45mSouthwest
Deal found 12/20$247
This Southwest deal was found by Cheapflights users on 12/18. 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.
Thu 12/258:15 amMDW - HOU
1 stop5h 40mSouthwest
Thu 1/18:45 amHOU - MDW
1 stop6h 10mSouthwest
Deal found 12/18$282
This American Airlines deal was found by Cheapflights users on 12/20. 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 12/318:25 amORD - HOU
1 stop7h 24mAmerican Airlines
Thu 1/14:17 pmHOU - ORD
1 stop6h 58mAmerican Airlines
Deal found 12/20$352
This Southwest deal was found by Cheapflights users on 12/19. 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 12/312:10 pmMDW - HOU
1 stop5h 25mSouthwest
Sun 1/410:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 12/19$378
This American Airlines deal was found by Cheapflights users on 12/20. 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 12/318:25 amORD - HOU
1 stop7h 24mAmerican Airlines
Sat 1/35:40 amHOU - ORD
1 stop5h 14mAmerican Airlines
Deal found 12/20$423
This Southwest deal was found by Cheapflights users on 12/20. 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 12/311:45 pmORD - HOU
2 stops6h 05mSouthwest
Thu 1/15:55 amHOU - ORD
1 stop9h 30mSouthwest
Deal found 12/20$462
This Southwest deal was found by Cheapflights users on 12/19. 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 12/311:45 pmORD - HOU
2 stops6h 05mSouthwest
Sun 1/46:00 amHOU - ORD
1 stop7h 00mSouthwest
Deal found 12/19$463
This Southwest deal was found by Cheapflights users on 12/18. 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 12/311:45 pmORD - HOU
1 stop5h 50mSouthwest
Sat 1/36:10 amHOU - ORD
2 stops6h 05mSouthwest
Deal found 12/18$498
This Southwest deal was found by Cheapflights users on 12/18. 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 12/311:45 pmORD - HOU
2 stops6h 05mSouthwest
Fri 1/26:00 amHOU - ORD
2 stops6h 15mSouthwest
Deal found 12/18$503
This American Airlines deal was found by Cheapflights users on 12/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:36 amORD - HOU
1 stop8h 11mAmerican Airlines
Thu 1/110:13 amHOU - ORD
1 stop7h 04mAmerican Airlines
Deal found 12/18$505
This Southwest deal was found by Cheapflights users on 12/19. 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 12/237:25 pmMDW - HOU
Nonstop2h 45mSouthwest
Thu 1/16:35 amHOU - MDW
Nonstop2h 25mSouthwest
Deal found 12/19$506

Find flight deals from Chicago to Galveston

Keep the following information in mind while searching for Chicago to Galveston flight deals. Data was last updated December 21, 2025.

Round-trip from

$145
(Southwest)

One-way from

$66
(Southwest)

Popular in

March

Cheapest in

January

Average price

$249
From Chicago (CHI) to Galveston
Search Deals
One-way flight from Chicago (CHI) to Galveston
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($8 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 December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Galveston 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 December 21, 2025.
Use the filters below to find and compare flights from Chicago to Galveston that are best for you.

Fly from

Chicago

Fly to

Galveston

Route

Depart

Return

Price

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 1/21

8:55 am-11:50 am

Nonstop2h 55m

Houston Hobby

Sat 1/24

11:25 am-1:50 pm

Nonstop2h 25m

$157

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 2/21

3:21 pm-10:28 pm

1 stop7h 07m

Houston Hobby

Wed 3/4

1:06 pm-7:19 pm

1 stop6h 13m

$197

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 1/17

2:50 pm-10:33 pm

1 stop7h 43m

Houston Hobby

Sat 1/24

11:09 am-4:59 pm

1 stop5h 50m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 2/6

8:30 pm-11:15 pm

Nonstop2h 45m

Houston Hobby

Fri 2/13

8:45 pm-11:10 pm

Nonstop2h 25m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/21

4:13 pm-10:28 pm

1 stop6h 15m

Houston Hobby

Wed 3/4

10:50 am-5:45 pm

1 stop6h 55m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/21

4:13 pm-10:28 pm

1 stop6h 15m

Houston Hobby

Sat 2/28

10:50 am-3:21 pm

1 stop4h 31m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 1/23

1:20 pm-5:50 pm

1 stop4h 30m

Houston Hobby

Sun 2/1

5:00 am-7:25 am

Nonstop2h 25m

$203

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sun 1/25

1:35 pm-7:05 pm

1 stop5h 30m

Houston Hobby

Sun 2/1

5:00 am-7:25 am

Nonstop2h 25m

$207

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 2/7

2:59 pm-10:33 pm

1 stop7h 34m

Houston Hobby

Mon 2/9

5:04 pm-11:56 pm

1 stop6h 52m

$207

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 1/24

11:15 am-4:10 pm

1 stop4h 55m

Houston Hobby

Mon 1/26

5:04 pm-11:56 pm

1 stop6h 52m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 42 results
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Best time to book a flight from Chicago to Galveston

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Galveston. Price data was last updated on December 12, 2025.

Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Galveston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Galveston (average of $56). Flying from Chicago to Galveston in June is currently the most expensive (average of $130). 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 CHI to G4L?

Find hourly flight availability from Chicago to Galveston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Galveston in the evening. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Galveston. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Galveston flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday evenings 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 Chicago to Galveston?

Reviews of airlines servicing Galveston

Get insights into the airlines that provide service to Galveston. 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 Galveston. Reviews last updated December 21, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago to Galveston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,099 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,050 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,194 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,082 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Galveston. 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 Chicago to Galveston?

    Southwest and Delta can get you from Chicago to Galveston in just under 2h 55m. Your travel time can differ by up to 4h 12m. The distance from Chicago to Galveston is about 938 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Galveston one-way?

    The cheapest airlines for a one-way flight from Chicago to Galveston are Frontier ($49), Spirit Airlines ($50), and American Airlines ($75).

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Chicago to Galveston (average of $56). Flying from Chicago to Galveston in June is currently the most expensive (average of $130). 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

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Top 6 airlines flying from Chicago to Galveston

Discover the top 6 airlines that operate flights from Chicago to Galveston. 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$174FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$74Average$172FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$130Average$344FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$262FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$178Average$343FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$287FlexibilityNo cancel feeOn-timeN/A

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