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$62+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Galveston to Chicago are usually found in September or April, booked 28 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

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 February 20, 2025.

Round-trip from

$127
(FlightHub)

One-way from

$62
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$187
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1210:36 amHOU - ORD
1 stop14h 08mFrontier
Tue 3/256:45 amORD - HOU
1 stop26h 51mFrontier
Deal found 2/18$127
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1210:36 amHOU - MDW
1 stop13h 41mFrontier
Tue 3/256:40 amMDW - HOU
1 stop26h 56mFrontier
Deal found 2/18$147
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 4/177:25 amHOU - MDW
Nonstop2h 25mSouthwest
Wed 4/231:25 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 2/20$197
This Southwest deal was found by Cheapflights users on 2/19. 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 3/186:30 amHOU - ORD
1 stop6h 35mSouthwest
Tue 3/2512:40 pmORD - HOU
1 stop8h 10mSouthwest
Deal found 2/19$217
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/186:00 amHOU - ORD
1 stop7h 45mDelta
Tue 3/255:30 pmORD - HOU
1 stop5h 36mDelta
Deal found 2/19$238
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/510:18 amHOU - ORD
1 stop7h 18mAmerican Airlines
Sat 4/125:00 amORD - HOU
1 stop4h 47mAmerican Airlines
Deal found 2/19$256
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2610:35 amHOU - MDW
1 stop7h 24mDelta
Tue 4/2912:48 pmMDW - HOU
1 stop5h 02mDelta
Deal found 2/19$257
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/269:38 amHOU - RFD
2 stops22h 17mAllegiant Air
Mon 6/308:45 amRFD - HOU
2 stops10h 26mAllegiant Air
Deal found 2/19$488

Find flights from Galveston to Chicago within your budget

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 February 20, 2025.

Fly from

Galveston

Fly to

Chicago

Route

Depart

Return

Price

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 3/12

10:36 am-12:44 am

1 stop14h 08m

Chicago O'Hare Intl

Tue 3/25

6:45 am-9:36 am

1 stop26h 51m

$127

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 3/12

10:36 am-12:17 am

1 stop13h 41m

Chicago Midway

Tue 3/25

6:40 am-9:36 am

1 stop26h 56m

$147

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 4/17

7:25 am-9:50 am

Nonstop2h 25m

Chicago Midway

Wed 4/23

1:25 pm-4:05 pm

Nonstop2h 40m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 3/18

6:30 am-1:05 pm

1 stop6h 35m

Chicago O'Hare Intl

Tue 3/25

12:40 pm-8:50 pm

1 stop8h 10m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 3/18

6:00 am-1:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 3/25

5:30 pm-11:06 pm

1 stop5h 36m

$238

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 4/5

10:18 am-5:36 pm

1 stop7h 18m

Chicago O'Hare Intl

Sat 4/12

5:00 am-9:47 am

1 stop4h 47m

$256

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 4/26

10:35 am-5:59 pm

1 stop7h 24m

Chicago Midway

Tue 4/29

12:48 pm-5:50 pm

1 stop5h 02m

$257

HoustonChicago

HOU - RFD

HOURFD

Houston Hobby

Sun 3/9

11:20 am-8:40 pm

2 stops33h 20m

Chicago Greater Rockford

Wed 3/12

9:13 am-4:18 pm

2 stops31h 05m

$872

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 4/9

10:36 am-12:21 am

1 stop13h 45m

$62

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 3/19

10:36 am-12:44 am

1 stop14h 08m

$63

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 19 results
1
2

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.

Travel insights for flights from Galveston to Chicago

Get recent, data-driven insights about flights from Galveston to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 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 $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 February 20, 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 Friday at noon when fares are most often at their lowest. Saturday at noon 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 February 20, 2025.
See what other customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 Frontier, with whom users have recently found tickets for as low as $62. However, be on the lookout for offers from Southwest 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 Galveston?

Book flights to Galveston if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$142FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$150FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$140Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$144Average$245FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$448FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$197Average$395FlexibilityNo cancel feeOn-time63%
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