HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$79+ Cheap flights from Galveston, TX to Midway (MDW)

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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Galveston to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Galveston to Chicago Midway are usually found in September or October, booked 90 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Galveston to Midway

Keep the following information in mind while searching for Galveston to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

May

Cheapest in

September

Average price

$184
From Galveston to Chicago Midway
Search Deals
One-way flight from Galveston to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Galveston to Midway

Cheapest flights from Galveston to Midway
Explore the most affordable flight options available from Galveston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/185:55 pmHOU - MDW
Nonstop2h 25mSouthwest
Mon 10/209:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/15$157
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2211:10 amHOU - MDW
Nonstop2h 25mSouthwest
Sat 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Deal found 9/14$163
This Southwest deal was found by Cheapflights users on 9/15. 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 10/118:05 pmHOU - MDW
Nonstop2h 20mSouthwest
Fri 10/179:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/15$177
This Southwest deal was found by Cheapflights users on 9/15. 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 10/236:00 amHOU - MDW
2 stops5h 25mSouthwest
Sat 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Deal found 9/15$178
This Southwest deal was found by Cheapflights users on 9/15. 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 10/237:00 pmHOU - MDW
1 stop5h 05mSouthwest
Sun 10/266:45 amMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/15$187
This Southwest deal was found by Cheapflights users on 9/14. 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 10/11:25 pmHOU - MDW
Nonstop2h 25mSouthwest
Wed 10/88:50 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/14$193
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/2410:25 pmHOU - MDW
Nonstop2h 20mSouthwest
Sun 10/266:45 amMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/15$197
This Southwest deal was found by Cheapflights users on 9/14. 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 10/306:00 amHOU - MDW
2 stops5h 25mSouthwest
Sun 11/25:00 amMDW - HOU
1 stop6h 15mSouthwest
Deal found 9/14$202

Cheapflights Fare Finder

 
Customize your flight search to find flights from Galveston to Midway 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 September 16, 2025.
Use the filters below to find and compare flights from Galveston to Chicago Midway Airport that are best for you.

Fly from

Galveston

Fly to

Midway

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/18

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

Mon 10/20

9:30 pm-12:05 am

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 10/14

9:15 pm-11:35 pm

Nonstop2h 20m

Chicago Midway

Tue 10/21

8:50 pm-11:25 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 12/4

6:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Sat 12/6

7:30 pm-10:15 pm

Nonstop2h 45m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/25

5:30 am-11:40 am

1 stop6h 10m

Chicago Midway

Mon 10/27

5:30 am-8:00 am

Nonstop2h 30m

$167

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 11/11

11:05 am-4:50 pm

1 stop5h 45m

Chicago Midway

Tue 11/11

6:15 pm-11:00 pm

1 stop4h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 10/23

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

Sun 10/26

6:45 am-9:20 am

Nonstop2h 35m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 11/4

7:15 am-12:45 pm

1 stop5h 30m

Chicago Midway

Tue 11/4

5:15 pm-10:25 pm

1 stop5h 10m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 10/30

6:00 am-11:25 am

2 stops5h 25m

Chicago Midway

Mon 11/3

10:00 am-3:00 pm

1 stop5h 00m

$182

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 10/24

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

Thu 10/30

7:50 am-1:50 pm

1 stop6h 00m

$187

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 10/24

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

Sun 10/26

6:45 am-9:20 am

Nonstop2h 35m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 20 results
1
2

Best time to book a flight from Galveston to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

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

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

Booking 90 days in advance of your planned departure date is, on average, the best time to get cheap flights from Galveston to Chicago Midway Airport. 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 Galveston to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Galveston to Chicago Midway Airport (average of $160). Flying from Galveston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MDW?

Find hourly flight availability from Galveston to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 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 Midway Airport as you normally would.

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

Use this chart to determine the cheapest time to fly round-trip from Galveston to Midway. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Galveston to Chicago Midway Airport flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 16, 2025.
See what other customers who have flown with Southwest and Frontier from Galveston to Chicago Midway Airport 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
4,242 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

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 Midway. 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 Midway Airport?

    Southwest can get you from Galveston to Chicago Midway Airport in just under 2h 25m. Your travel time will be generally consistent. The distance from Galveston to Chicago Midway Airport is about 938 mi. All flights are typically nonstop.

  • What are the cheapest flights from Galveston to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Houston Hobby - Chicago Midway) can be booked for $73 on average, our data indicates $297 when flying from Galveston to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Galveston to Midway 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 Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Galveston to Chicago Midway Airport (average of $160). Flying from Galveston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Galveston to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Austin to O'Hare Intl flights
Hobby to Midway flights
Hobby to O'Hare Intl flights
Love Field to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Love Field to Midway flights
Austin to Midway flights
George Bush Intcntl to Midway flights
San Antonio to O'Hare Intl flights
El Paso to O'Hare Intl flights
San Antonio to Midway flights
El Paso to Midway flights
McAllen to O'Hare Intl flights
Harlingen to O'Hare Intl flights
Corpus Christi to O'Hare Intl flights
Brownsville to O'Hare Intl flights
Austin to Rockford flights
McAllen to Midway flights
Lubbock to O'Hare Intl flights
Amarillo to O'Hare Intl flights
Waco to O'Hare Intl flights
Killeen to O'Hare Intl flights
Laredo to O'Hare Intl flights
Midland to O'Hare Intl flights
Texarkana to O'Hare Intl flights
Hobby to Rockford flights
College Station to O'Hare Intl flights
San Antonio to Rockford flights
Longview to O'Hare Intl flights

Top 3 airlines flying from Galveston to Midway

Discover the top 3 airlines that operate flights from Galveston to Midway. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$81Average$174FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$284FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$331FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.