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$51+ Cheap flights from George Bush Intcntl (IAH) 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
IAH — MDW
Oct 18 — Oct 251
Sat 10/18
Sat 10/25
1 adult, Economy
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Cheap flight deals from George Bush Intcntl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from George Bush Intcntl (IAH) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 18, 2025.

Round-trip from

$97
(Frontier)

One-way from

$51
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$126

Good round-trip deal

$108 or less

Good one-way deal

$109 or less
From Houston George Bush Intcntl to Chicago Midway
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One-way flight from Houston George Bush Intcntl to Chicago Midway
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Highest demand for flights based on searches. 15% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Houston George Bush Intcntl to Chicago Midway.
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Price to beat on a one-way flight from Houston George Bush Intcntl to Chicago Midway.
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Find flight deals from George Bush Intcntl to Midway

Cheapest flights from George Bush Intcntl to Midway
Explore the most affordable flight options available from George Bush Intcntl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2025.

This Frontier deal was found by Cheapflights users on 9/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:39 pmIAH - MDW
Nonstop2h 30mFrontier
Fri 10/3112:30 pmMDW - IAH
1 stop11h 09mFrontier
Deal found 9/17$97
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/92:12 pmIAH - MDW
Nonstop2h 30mFrontier
Sat 10/1110:00 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/16$103
This Frontier deal was found by Cheapflights users on 9/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:39 pmIAH - MDW
Nonstop2h 30mFrontier
Tue 10/218:05 amMDW - IAH
1 stop8h 42mFrontier
Deal found 9/18$104
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/245:42 pmIAH - MDW
1 stop6h 04mFrontier
Thu 10/306:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/16$108
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:39 pmIAH - MDW
Nonstop2h 30mFrontier
Mon 10/206:15 amMDW - IAH
1 stop10h 32mFrontier
Deal found 9/15$109
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/232:12 pmIAH - MDW
Nonstop2h 30mFrontier
Sun 10/265:20 amMDW - IAH
1 stop11h 18mFrontier
Deal found 9/15$114
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/162:12 pmIAH - MDW
Nonstop2h 30mFrontier
Mon 10/209:00 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/15$117
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:39 pmIAH - MDW
Nonstop2h 30mFrontier
Sat 10/2510:00 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/16$118
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/92:12 pmIAH - MDW
Nonstop2h 30mFrontier
Sat 10/1810:00 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/16$119
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:05 amIAH - MDW
1 stop5h 33mFrontier
Sat 10/2510:00 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/16$120
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/232:12 pmIAH - MDW
Nonstop2h 30mFrontier
Mon 10/279:45 amMDW - IAH
1 stop6h 58mFrontier
Deal found 9/16$122
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:04 amIAH - MDW
Nonstop2h 33mFrontier
Sun 11/166:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/16$123

Cheapflights Fare Finder

 
Customize your flight search to find flights from George Bush Intcntl 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 18, 2025.
Use the filters below to find and compare flights from Houston George Bush Intcntl Airport to Chicago Midway Airport that are best for you.

Fly from

George Bush Intcntl

Fly to

Midway

Route

Depart

Return

Price

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 12/11

5:29 pm-11:05 pm

1 stop5h 36m

Chicago Midway

Fri 12/12

7:00 am-10:17 am

Nonstop3h 17m

$152

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sun 11/9

11:33 am-12:30 am

1 stop12h 57m

Chicago Midway

Mon 11/17

1:37 pm-10:08 pm

1 stop8h 31m

$154

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 10/30

10:04 am-12:37 pm

Nonstop2h 33m

Chicago Midway

Sun 11/2

6:06 pm-3:36 pm

1 stop21h 30m

$156

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 10/24

12:39 pm-3:12 pm

Nonstop2h 33m

Chicago Midway

Sun 10/26

10:30 am-1:22 pm

Nonstop2h 52m

$159

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Mon 11/10

10:04 am-12:37 pm

Nonstop2h 33m

Chicago Midway

Mon 11/17

1:37 pm-10:08 pm

1 stop8h 31m

$162

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 10/24

12:39 pm-3:12 pm

Nonstop2h 33m

Chicago Midway

Mon 10/27

9:00 am-11:49 am

Nonstop2h 49m

$173

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 10/9

5:42 pm-11:46 pm

1 stop6h 04m

Chicago Midway

Sun 10/12

5:20 am-4:38 pm

1 stop11h 18m

$205

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 10/18

12:55 pm-6:25 pm

1 stop5h 30m

Chicago Midway

Tue 10/28

10:35 am-3:26 pm

1 stop4h 51m

$217

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 11/12

7:01 am-11:52 am

1 stop4h 51m

Chicago Midway

Mon 11/17

1:14 pm-6:20 pm

1 stop5h 06m

$217

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Tue 3/3

5:25 am-12:35 pm

1 stop7h 10m

Chicago Midway

Wed 3/4

9:30 am-2:55 pm

1 stop5h 25m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 22 results
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The best insider tips for Houston George Bush Intcntl Airport to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Houston George Bush Intcntl Airport to Chicago Midway Airport trip
Airports
IAH

Check security wait times on the IAH website to plan your arrival and avoid delays.

Read more about IAHby Evie Carrick
MDW

Use the 'L' train for a quick, affordable ride to Chicago's city center from MDW in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Evie Carrick

Evie Carrick

Expert on IAH

Evie Carrick

Evie Carrick

Evie Carrick is a writer and editor who has lived in five countries and traveled to over 50, with extensive experience flying around the world. She was born in Colorado, but has spent time flying to both coasts to visit family. She writes regularly for Travel + Leisure, BuzzFeed, and SKI and recently published seven travel journals with Simon & Schuster.

Read more

Best time to book a flight from George Bush Intcntl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from George Bush Intcntl 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 Houston George Bush Intcntl Airport to Chicago Midway Airport

What is the cheapest month to book a flight from Houston George Bush Intcntl Airport to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Houston George Bush Intcntl Airport to Chicago Midway Airport (average of $160). Flying from Houston George Bush Intcntl Airport 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 IAH to MDW?

Find hourly flight availability from George Bush Intcntl 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 18, 2025.

One of the essential ways to save on airfare from Houston George Bush Intcntl Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 42% on airfare.

What is the cheapest day to fly from Houston George Bush Intcntl Airport to Chicago Midway Airport?

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

Travelers seeking maximum savings on their Houston George Bush Intcntl Airport to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Wednesday afternoons 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 18, 2025.
Read through reviews of airlines operating flights from Houston George Bush Intcntl Airport to Chicago Midway Airport, such as Delta and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.8
Fair
3,174 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from George Bush Intcntl 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 Houston George Bush Intcntl Airport to Chicago Midway Airport?

    Airlines like Frontier fly from Houston George Bush Intcntl Airport to Chicago Midway Airport in about 5h 36m. The time it takes to get you to your destination can typically vary by up to . There are 918 mi between Houston George Bush Intcntl Airport and Chicago Midway Airport.

  • What are the cheapest airlines flying from Houston George Bush Intcntl Airport to Chicago Midway Airport round-trip?

    Currently priced at $81, Frontier will fly you from Houston George Bush Intcntl Airport to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Delta for as low as $216. Frontier is priced at 60% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Houston George Bush Intcntl Airport to Chicago Midway Airport?

    While on average a flight from Houston George Bush Intcntl Airport to Chicago Midway Airport is generally $160, our data shows the cheapest flight currently is $67. When looking at the most popular route, (Houston George Bush Intcntl - Chicago Midway), you can expect to pay $103 for that flight.

  • Can I find deals for flights from George Bush Intcntl to Midway that include hotel bookings?

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

  • How can I find direct flights from George Bush Intcntl to Midway?

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

  • Can I find deals for business class flights from George Bush Intcntl to Midway?

    Yes. Cheapflights offers flight deals from George Bush Intcntl 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 Houston George Bush Intcntl Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Houston George Bush Intcntl Airport to Chicago Midway Airport (average of $160). Flying from Houston George Bush Intcntl Airport 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

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Alternative routes for George Bush Intcntl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Hobby to Midway flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights

Top 2 airlines flying from George Bush Intcntl to Midway

Discover the top 2 airlines that operate flights from George Bush Intcntl 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$81Average$173FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$331FlexibilityNo cancel feeOn-timeN/A

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