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Galveston

$59+ Cheap flights from Midway (MDW) to Galveston, TX

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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HOU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Galveston are usually found in September or February, booked 53 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Find flight deals from Midway to Galveston

Cheapest flights from Midway to Galveston
Explore the most affordable flight options available from Midway to Galveston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

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.
Wed 12/108:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Wed 12/172:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 10/27$157
This Southwest deal was found by Cheapflights users on 10/26. 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 12/25:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Sat 12/66:10 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 10/26$158
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.
Sat 12/64:30 pmMDW - HOU
Nonstop2h 45mSouthwest
Sun 12/149:50 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 10/28$177
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.
Tue 12/21:05 pmMDW - HOU
Nonstop2h 45mSouthwest
Thu 12/47:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 10/27$178
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 12/58:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Sun 12/79:50 pmHOU - MDW
Nonstop2h 20mSouthwest
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 11/279:25 amMDW - HOU
1 stop5h 15mSouthwest
Thu 12/410:20 amHOU - MDW
Nonstop2h 25mSouthwest
Deal found 10/28$202
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.
Mon 11/175:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Tue 11/186:35 amHOU - MDW
Nonstop2h 25mSouthwest
Deal found 10/27$208
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.
Wed 12/318:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Thu 1/16:35 amHOU - MDW
Nonstop2h 25mSouthwest
Deal found 10/27$210

Cheap flight deals from Midway to Galveston

Keep the following information in mind while searching for Midway to Galveston flight deals. Data was last updated October 29, 2025.

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

July

Cheapest in

September

Average price

$237
From Chicago Midway to Galveston
Search Deals
One-way flight from Chicago Midway to Galveston
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Galveston 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 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Galveston that are best for you.

Fly from

Midway

Fly to

Galveston

Route

Depart

Return

Price

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 1/10

7:35 pm-10:25 pm

Nonstop2h 50m

Houston Hobby

Sun 1/11

6:30 am-8:50 am

Nonstop2h 20m

$117

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 1/10

7:35 pm-10:25 pm

Nonstop2h 50m

Houston Hobby

Mon 1/12

6:40 am-9:05 am

Nonstop2h 25m

$117

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 11/27

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Tue 12/2

6:00 am-11:55 am

1 stop5h 55m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 12/6

4:29 pm-10:33 pm

1 stop6h 04m

Houston Hobby

Sun 12/14

6:47 pm-11:47 pm

1 stop5h 00m

$207

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sun 1/11

5:55 am-8:50 am

Nonstop2h 55m

Houston Hobby

Sat 1/17

11:00 am-5:25 pm

2 stops6h 25m

$215

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 12/5

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Sun 12/7

6:00 am-11:55 am

1 stop5h 55m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 12/12

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Sun 12/14

6:47 pm-11:47 pm

1 stop5h 00m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 11/11

2:10 pm-7:35 pm

1 stop5h 25m

Houston Hobby

Tue 11/18

10:20 am-12:45 pm

Nonstop2h 25m

$224

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 12/11

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Thu 12/18

6:00 am-11:58 am

1 stop5h 58m

$245

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 12/31

6:15 pm-11:00 pm

1 stop4h 45m

Houston Hobby

Thu 1/1

5:40 am-11:25 am

1 stop5h 45m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 22 results
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Best time to book a flight from Midway to Galveston

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

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to Galveston. Price data was last updated on October 24, 2025.

The price you pay for your flight from Chicago Midway Airport to Galveston may vary depending on when you book. For the best chance of a lower fare, look to book 53 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago Midway Airport to Galveston?

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Galveston (average of $74). Flying from Chicago Midway Airport to Galveston in July is currently the most expensive (average of $184). 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 MDW to G4L?

Find hourly flight availability from Midway to Galveston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 41% on flights from Chicago Midway Airport to Galveston by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Galveston. Price data was last updated on December 16, 2024.

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

Reviews of airlines servicing Galveston

Get insights into the airlines that provide service to Galveston. 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 Galveston. Reviews last updated October 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Spirit Airlines, and Frontier from Chicago Midway Airport to Galveston to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,124 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Galveston. 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 Chicago Midway Airport to Galveston?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Galveston in about 2h 50m. The time it takes to get you to your destination can typically vary by up to 4h 38m. There are 938 mi between Chicago Midway Airport and Galveston. This flight may include one or multiple stops.

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

    The cheapest flight price from Chicago Midway Airport to Galveston is $78. On average you can expect to pay $271. The most popular route, (Chicago Midway - Houston Hobby), can usually be booked for $84.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Galveston (average of $74). Flying from Chicago Midway Airport to Galveston in July is currently the most expensive (average of $184). 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.

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Top 4 airlines flying from Midway to Galveston

Discover the top 4 airlines that operate flights from Midway to Galveston. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$88Average$187FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$116Average$195FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$178Average$333FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$287FlexibilityNo cancel feeOn-timeN/A

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