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$54+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Galveston to Chicago are usually found in September or April, booked 75 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

Cheap flight deals from Galveston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Galveston (G4L) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$136
(Trip.com)

One-way from

$54
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$189
From Galveston to Chicago (CHI)
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One-way flight from Galveston to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 21, 2025.

This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2610:36 amHOU - MDW
1 stop13h 41mFrontier
Sat 3/16:40 amMDW - HOU
1 stop8h 03mFrontier
Deal found 1/21$136
This Southwest deal was found by Cheapflights users on 1/21. 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 2/116:55 amHOU - MDW
Nonstop2h 20mSouthwest
Tue 2/111:05 pmMDW - HOU
1 stop4h 40mSouthwest
Deal found 1/21$177
This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2110:36 amHOU - ORD
1 stop14h 08mFrontier
Sun 2/236:50 amORD - HOU
1 stop26h 46mFrontier
Deal found 1/20$177
This Southwest deal was found by Cheapflights users on 1/21. 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 2/118:00 amHOU - ORD
1 stop5h 00mSouthwest
Tue 2/113:10 pmORD - HOU
1 stop7h 45mSouthwest
Deal found 1/21$191
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2710:25 amHOU - ORD
1 stop7h 00mDelta
Sat 3/12:55 pmORD - HOU
1 stop6h 30mDelta
Deal found 1/20$217
This Delta deal was found by Cheapflights users on 1/19. 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 2/46:00 amHOU - MDW
1 stop5h 59mDelta
Tue 2/115:05 pmMDW - HOU
1 stop5h 24mDelta
Deal found 1/19$237
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Thu 2/66:00 amHOU - ORD
1 stop5h 12mAmerican Airlines
Sun 2/95:00 amORD - HOU
1 stop4h 41mAmerican Airlines
Deal found 1/20$297
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Fri 6/208:30 amHOU - MDW
1 stop5h 33mAllegiant Air
Mon 6/2310:34 amMDW - HOU
1 stop8h 37mAllegiant Air
Deal found 1/21$341
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/65:08 pmHOU - RFD
2 stops24h 52mAllegiant Air
Sun 3/911:33 amRFD - HOU
2 stops21h 10mAllegiant Air
Deal found 1/20$859

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 2/26

10:36 am-12:17 am

1 stop13h 41m

Chicago Midway

Sat 3/1

6:40 am-2:43 pm

1 stop8h 03m

$136

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 4/1

4:55 pm-9:25 pm

1 stop4h 30m

Chicago Midway

Tue 4/15

6:00 pm-8:50 pm

Nonstop2h 50m

$169

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 2/21

10:36 am-12:44 am

1 stop14h 08m

Chicago O'Hare Intl

Sun 2/23

6:50 am-9:36 am

1 stop26h 46m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 2/11

8:00 am-1:00 pm

1 stop5h 00m

Chicago O'Hare Intl

Tue 2/11

3:10 pm-10:55 pm

1 stop7h 45m

$191

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 2/27

10:25 am-5:25 pm

1 stop7h 00m

Chicago O'Hare Intl

Mon 3/3

2:59 pm-10:29 pm

1 stop7h 30m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 2/4

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Tue 2/11

5:05 pm-10:29 pm

1 stop5h 24m

$237

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 2/6

6:00 am-11:12 am

1 stop5h 12m

Chicago O'Hare Intl

Sun 2/9

5:00 am-9:41 am

1 stop4h 41m

$297

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 6/20

8:30 am-2:03 pm

1 stop5h 33m

Chicago Midway

Mon 6/23

10:34 am-7:11 pm

1 stop8h 37m

$341

HoustonChicago

HOU - RFD

HOURFD

Houston Hobby

Thu 3/6

5:08 pm-6:00 pm

2 stops24h 52m

Chicago Greater Rockford

Sun 3/9

11:33 am-8:43 am

2 stops21h 10m

$859

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 2/5

6:16 pm-12:17 am

1 stop6h 01m

$55

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 18 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 January 17, 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 $320). 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 January 21, 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 Wednesday evenings when fares are most often at their lowest. Monday 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 January 21, 2025.
See what other customers who have flown with Southwest, American 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
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

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

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

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
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

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

Sun Country Air
7.0
Good
386 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

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 $54. However, be on the lookout for offers from Southwest and Delta, 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 $320). 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$143FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$152FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$142Average$331FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$144Average$247FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$195Average$376FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$441FlexibilityNo cancel feeOn-timeN/A
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