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$66+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheapflights Tip: The best prices from Galveston to Chicago are usually found in February or January, booked 63 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap 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 December 23, 2025.

This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:25 pmHOU - MDW
1 stop6h 57mDelta
Wed 1/711:21 amMDW - HOU
1 stop4h 49mDelta
Deal found 12/21$237
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:25 pmHOU - MDW
1 stop6h 57mDelta
Thu 1/811:21 amMDW - HOU
1 stop4h 49mDelta
Deal found 12/21$257
This Southwest deal was found by Cheapflights users on 12/21. 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.
Wed 12/317:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Wed 1/78:55 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 12/21$277
This Southwest deal was found by Cheapflights users on 12/22. 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 12/317:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Thu 1/88:55 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 12/22$297
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/319:05 amHOU - ORD
1 stop6h 40mAmerican Airlines
Wed 1/76:54 amORD - HOU
1 stop5h 15mAmerican Airlines
Deal found 12/22$297
This Southwest deal was found by Cheapflights users on 12/22. 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 12/316:00 amHOU - ORD
1 stop7h 00mSouthwest
Wed 1/77:15 amORD - HOU
2 stops10h 40mSouthwest
Deal found 12/22$302
This Southwest deal was found by Cheapflights users on 12/22. 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 12/316:00 amHOU - ORD
1 stop7h 00mSouthwest
Thu 1/81:00 pmORD - HOU
1 stop9h 15mSouthwest
Deal found 12/22$317
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:25 pmHOU - MDW
1 stop6h 57mDelta
Tue 1/611:21 amMDW - HOU
1 stop4h 49mDelta
Deal found 12/21$328
This Southwest deal was found by Cheapflights users on 12/21. 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.
Wed 12/316:00 amHOU - ORD
1 stop7h 00mSouthwest
Fri 1/911:55 amORD - HOU
2 stops7h 55mSouthwest
Deal found 12/21$357
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:25 pmHOU - MDW
1 stop6h 57mDelta
Sun 1/45:05 pmMDW - HOU
1 stop6h 07mDelta
Deal found 12/21$398
This Southwest deal was found by Cheapflights users on 12/21. 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.
Sat 12/276:10 amHOU - ORD
1 stop6h 50mSouthwest
Thu 1/811:55 amORD - HOU
1 stop7h 45mSouthwest
Deal found 12/21$492
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.
Sat 12/277:30 amHOU - ORD
1 stop7h 55mSouthwest
Sat 1/35:15 pmORD - HOU
1 stop5h 00mSouthwest
Deal found 12/20$531

Find flight deals from Galveston to Chicago

Keep the following information in mind while searching for Galveston to Chicago flight deals. Data was last updated December 23, 2025.

Round-trip from

$145
(Southwest)

One-way from

$66
(Southwest)

Popular in

June

Cheapest in

February

Average price

$209
From Galveston to Chicago (CHI)
Search Deals
One-way flight from Galveston to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($26 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 December 2025
Search Deals

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 December 23, 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

Sat 2/14

5:55 am-8:20 am

Nonstop2h 25m

Chicago Midway

Sat 2/14

5:50 pm-8:40 pm

Nonstop2h 50m

$160

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 1/21

6:40 am-9:05 am

Nonstop2h 25m

Chicago Midway

Wed 1/28

8:55 am-11:50 am

Nonstop2h 55m

$168

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/17

6:00 pm-8:25 pm

Nonstop2h 25m

Chicago Midway

Mon 1/19

8:00 am-12:30 pm

1 stop4h 30m

$175

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/24

11:25 am-1:50 pm

Nonstop2h 25m

Chicago Midway

Mon 1/26

6:15 am-9:15 am

Nonstop3h 00m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/17

6:10 am-11:35 am

1 stop5h 25m

Chicago Midway

Sun 1/18

8:55 am-11:50 am

Nonstop2h 55m

$183

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 2/12

8:45 pm-11:10 pm

Nonstop2h 25m

Chicago Midway

Sat 2/14

5:50 pm-8:40 pm

Nonstop2h 50m

$187

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/31

6:10 am-11:35 am

1 stop5h 25m

Chicago Midway

Sat 2/7

8:20 am-11:20 am

Nonstop3h 00m

$187

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 1/21

11:09 am-5:29 pm

1 stop6h 20m

Chicago Midway

Wed 1/28

10:46 am-4:10 pm

1 stop5h 24m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 1/27

5:04 pm-10:22 pm

1 stop5h 18m

Chicago Midway

Tue 2/3

10:48 am-4:10 pm

1 stop5h 22m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 2/5

6:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

Mon 2/9

8:30 pm-11:15 pm

Nonstop2h 45m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 50 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 December 19, 2025.

To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 63 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, January is the cheapest month in which you can book a flight from Galveston to Chicago (average of $53). Flying from Galveston to Chicago in May is currently the most expensive (average of $95). 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 December 23, 2025.

One of the essential ways to save on airfare from Galveston to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 49% on airfare.

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 Thursday afternoons when fares are most often at their lowest. Sunday 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 December 23, 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
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
3,075 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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 5h 29m. 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 Frontier, with whom users have recently found tickets for as low as $28. However, be on the lookout for offers from Spirit Airlines and Southwest, 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, January is the cheapest month in which you can book a flight from Galveston to Chicago (average of $53). Flying from Galveston to Chicago in May is currently the most expensive (average of $95). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$188FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$76Average$163FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$134Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$264FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$167Average$274FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$383FlexibilityNo cancel feeOn-timeN/A

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