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$90+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
mai 6 — mai 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Galveston to Chicago are usually found in September or February, booked 80 days in advance, depart on a Wednesday or Friday 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 mai 1, 2025.

Round-trip from

$189
(Southwest)

One-way from

$90
(Southwest)

Popular in

March

Cheapest in

September

Average price

$174
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. 4% potential increase in price ($8 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 May 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 mai 1, 2025.

This Southwest deal was found by Cheapflights users on 4/29. 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.
mer. 7/25:45 amHOU - MDW
Nonstop2h 25mSouthwest
mer. 7/29:40 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 4/29$179
This Delta deal was found by Cheapflights users on 4/30. 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.
sam. 7/2612:50 pmHOU - ORD
1 stop6h 44mDelta
mer. 7/307:00 amORD - HOU
1 stop5h 01mDelta
Deal found 4/30$217
This Southwest deal was found by Cheapflights users on 4/29. 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.
sam. 5/315:55 amHOU - ORD
1 stop5h 55mSouthwest
mar. 6/35:45 pmORD - HOU
1 stop4h 25mSouthwest
Deal found 4/29$228
This American Airlines deal was found by Cheapflights users on 4/30. 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.
sam. 5/246:31 pmHOU - ORD
1 stop5h 25mAmerican Airlines
ven. 5/308:05 amORD - HOU
1 stop5h 53mAmerican Airlines
Deal found 4/30$257
This Delta deal was found by Cheapflights users on 4/30. 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.
mar. 7/16:00 amHOU - MDW
1 stop5h 59mDelta
ven. 7/46:00 amMDW - HOU
1 stop14h 44mDelta
Deal found 4/30$264
This Mytrip deal was found by Cheapflights users on 4/30. 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.
ven. 6/1310:39 amHOU - MDW
1 stop9h 07mAllegiant Air
ven. 6/2710:34 amMDW - HOU
1 stop8h 37mAllegiant Air
Deal found 4/30$265
This Sun Country Air deal was found by Cheapflights users on 4/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/296:30 pmHOU - ORD
1 stop17h 57mSun Country Air
dim. 6/17:00 amORD - HOU
1 stop10h 33mSun Country Air
Deal found 4/30$295
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/36:00 pmHOU - ORD
2 stops29h 59mMultiple Airlines
dim. 7/66:45 amORD - HOU
1 stop10h 27mMultiple Airlines
Deal found 4/30$462

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 mai 1, 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

mer. 7/2

5:45 am-8:10 am

Nonstop2h 25m

Chicago Midway

mer. 7/2

9:40 pm-12:10 am

Nonstop2h 30m

$179

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

sam. 7/26

6:00 am-12:31 pm

1 stop6h 31m

Chicago O'Hare Intl

mar. 7/29

7:00 am-12:01 pm

1 stop5h 01m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

sam. 5/31

5:55 am-11:50 am

1 stop5h 55m

Chicago O'Hare Intl

mar. 6/3

5:45 pm-10:10 pm

1 stop4h 25m

$228

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

sam. 5/24

6:31 pm-11:56 pm

1 stop5h 25m

Chicago O'Hare Intl

ven. 5/30

8:05 am-1:58 pm

1 stop5h 53m

$257

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mar. 7/1

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

ven. 7/4

6:00 am-8:44 pm

1 stop14h 44m

$264

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

ven. 6/13

10:39 am-7:46 pm

1 stop9h 07m

Chicago Midway

ven. 6/27

10:34 am-7:11 pm

1 stop8h 37m

$265

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

jeu. 5/29

6:30 pm-12:27 pm

1 stop17h 57m

Chicago O'Hare Intl

dim. 6/1

7:00 am-5:33 pm

1 stop10h 33m

$295

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

jeu. 7/3

6:00 pm-11:59 pm

2 stops29h 59m

Chicago O'Hare Intl

dim. 7/6

6:45 am-5:12 pm

1 stop10h 27m

$462

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mer. 7/2

5:45 am-8:10 am

Nonstop2h 25m

$90

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

mer. 6/4

6:00 am-11:53 am

1 stop5h 53m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 17 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.

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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 80 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 mai 1, 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. Sunday afternoons 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 mai 1, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air 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
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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.
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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.
Sun Country Air
6.9
Okay
346 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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.

  • 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 $90. 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 Galveston?

Book flights to Galveston if you plan to visit one of these locations
Merrillville
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 mai 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$52Average$146FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$151FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$145Average$250FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$148Average$338FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$190Average$338FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$395FlexibilityNo cancel feeOn-timeN/A

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