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Midway

$59+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 Saturday 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 October 30, 2025.

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

May

Cheapest in

September

Average price

$209
From Galveston to Chicago Midway
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One-way flight from Galveston to Chicago Midway
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Highest demand for flights based on searches. 10% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/28. 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 12/316:35 amHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/66:15 amMDW - HOU
Nonstop3h 00mSouthwest
Deal found 10/28$152
This Southwest deal was found by Cheapflights users on 10/29. 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.
Wed 12/36:35 amHOU - MDW
Nonstop2h 25mSouthwest
Wed 12/35:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 10/29$157
This Southwest deal was found by Cheapflights users on 10/29. 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.
Tue 12/92:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Fri 12/129:55 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 10/29$177
This Southwest deal was found by Cheapflights users on 10/28. 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 12/32:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Mon 12/810:50 amMDW - HOU
1 stop5h 55mSouthwest
Deal found 10/28$187
This Southwest deal was found by Cheapflights users on 10/27. 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 11/287:25 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 12/21:05 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 10/27$194
This Southwest deal was found by Cheapflights users on 10/28. 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 12/57:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Sun 12/79:55 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 10/28$197
This Southwest deal was found by Cheapflights users on 10/28. 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 11/278:20 amHOU - MDW
1 stop4h 20mSouthwest
Thu 12/48:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 10/28$198
This Southwest deal was found by Cheapflights users on 10/28. 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 12/241:15 pmHOU - MDW
1 stop5h 50mSouthwest
Tue 1/66:15 amMDW - HOU
Nonstop3h 00mSouthwest
Deal found 10/28$210
This Southwest deal was found by Cheapflights users on 10/29. 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.
Wed 11/126:35 amHOU - MDW
Nonstop2h 25mSouthwest
Wed 11/197:00 amMDW - HOU
Nonstop2h 40mSouthwest
Deal found 10/29$214
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:39 amHOU - MDW
1 stop5h 39mDelta
Sun 12/75:13 pmMDW - HOU
1 stop5h 35mDelta
Deal found 10/29$217

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 October 30, 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

Tue 1/6

12:50 pm-6:05 pm

1 stop5h 15m

Chicago Midway

Fri 1/9

7:55 pm-10:40 pm

Nonstop2h 45m

$193

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/3

6:00 am-11:55 am

1 stop5h 55m

Chicago Midway

Wed 12/3

5:29 pm-10:48 pm

1 stop5h 19m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 12/5

6:47 pm-11:47 pm

1 stop5h 00m

Chicago Midway

Sun 12/7

5:13 pm-10:48 pm

1 stop5h 35m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 12/5

7:30 am-12:40 pm

1 stop5h 10m

Chicago Midway

Mon 12/8

5:00 am-11:15 am

1 stop6h 15m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 12/12

6:47 pm-11:47 pm

1 stop5h 00m

Chicago Midway

Sun 12/14

6:00 am-1:28 pm

1 stop7h 28m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 11/12

3:50 pm-8:15 pm

1 stop4h 25m

Chicago Midway

Wed 11/19

5:15 pm-8:00 pm

Nonstop2h 45m

$224

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/31

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Mon 1/5

6:10 pm-12:10 am

1 stop6h 00m

$230

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 12/16

6:00 am-11:55 am

1 stop5h 55m

Chicago Midway

Fri 12/19

12:50 pm-5:52 pm

1 stop5h 02m

$267

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 1/5

7:10 am-12:45 pm

1 stop5h 35m

Chicago Midway

Thu 1/8

10:15 am-4:45 pm

1 stop6h 30m

$271

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 11/14

7:25 pm-9:50 pm

Nonstop2h 25m

Chicago Midway

Sat 11/15

11:00 am-5:00 pm

1 stop6h 00m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 21 results
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2
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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 October 24, 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, January is the cheapest month in which you can book a flight from Galveston to Chicago Midway Airport (average of $53). Flying from Galveston to Chicago Midway Airport in August is currently the most expensive (average of $123). 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 October 30, 2025.

It’s typically best to fly out from Galveston to Chicago Midway Airport in the evening. Doing so could potentially save you 22% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 October 26, 2025.

Travelers seeking maximum savings on their Galveston to Chicago Midway Airport flight should consider departing on Monday at noon 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.

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 October 30, 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

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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 and Delta can get you from Galveston to Chicago Midway Airport in just under 5h 15m. Your travel time can differ by up to 40m. The distance from Galveston to Chicago Midway Airport is about 938 mi. This flight may include one or multiple stops.

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

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Houston Hobby - Chicago Midway) can be booked for $84 on average, our data indicates $284 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, January is the cheapest month in which you can book a flight from Galveston to Chicago Midway Airport (average of $53). Flying from Galveston to Chicago Midway Airport in August is currently the most expensive (average of $123). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$88Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$171Average$281FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$346FlexibilityNo cancel feeOn-timeN/A

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