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$90+ Cheap flights from Hobby (HOU) 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago Midway are usually found in August or June, booked 90 days in advance, depart on a Wednesday or Friday and return on a Wednesday

Cheap flight deals from Hobby to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) 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 April 24, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$188
(Southwest)

One-way from

$90
(Southwest)

Popular in

December

Cheapest in

August

Average price

$256

Good round-trip deal

$250 or less

Good one-way deal

$158 or less
Provider with most accurate pricing for Houston Hobby-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Houston Hobby-Chicago Midway flights.
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From Houston Hobby to Chicago Midway
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One-way flight from Houston Hobby to Chicago Midway
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Highest demand for flights based on searches. 14% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Houston Hobby to Chicago Midway.
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Price to beat on a one-way flight from Houston Hobby to Chicago Midway.
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Find flight deals from Hobby to Midway

Cheapest flights from Hobby to Midway
Explore the most affordable flight options available from Hobby to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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 5/249:00 pmHOU - MDW
Nonstop2h 30mSouthwest
Tue 5/278:45 amMDW - HOU
Nonstop2h 45mSouthwest
Deal found 4/23$188
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 6/710:22 amHOU - MDW
1 stop4h 58mDelta
Tue 6/106:00 amMDW - HOU
1 stop6h 10mDelta
Deal found 4/23$217
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/228:06 pmHOU - MDW
2 stops17h 58mMultiple Airlines
Sun 5/2511:03 amMDW - HOU
2 stops26h 40mMultiple Airlines
Deal found 4/23$474

Cheapflights Fare Finder

Customize your flight search to find flights from Hobby 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 April 24, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago Midway Airport that are best for you.

Fly from

Hobby

Fly to

Midway

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 5/24

9:00 pm-11:30 pm

Nonstop2h 30m

Chicago Midway

Tue 5/27

8:45 am-11:30 am

Nonstop2h 45m

$188

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 6/7

10:22 am-3:20 pm

1 stop4h 58m

Chicago Midway

Tue 6/10

6:00 am-12:10 pm

1 stop6h 10m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 5/22

8:06 pm-2:04 pm

2 stops17h 58m

Chicago Midway

Sun 5/25

11:03 am-1:43 pm

2 stops26h 40m

$474

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 5/24

9:00 pm-11:30 pm

Nonstop2h 30m

$90

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 6/16

10:39 am-7:46 pm

1 stop9h 07m

$103

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 5/28

6:00 am-11:53 am

1 stop5h 53m

$109

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 5/25

9:16 am-8:22 am

2 stops23h 06m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Compare providers for flights from Hobby to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hobby to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy1 starTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago Midway Airport flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Houston Hobby Airport-Chicago Midway Airport flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Houston Hobby Airport-Chicago Midway Airport flights, Cheapflights users trust Mytrip the most. Mytrip has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Houston Hobby Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Hobby to Midway

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

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

Use this chart to determine the optimal time to book a round-trip flight from Hobby to Midway. Price data was last updated on April 18, 2025.

The price you pay for your flight from Houston Hobby Airport to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 90 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 Houston Hobby Airport to Chicago Midway Airport?

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

Find hourly flight availability from Hobby 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 April 24, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 39% on flights from Houston Hobby Airport to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Hobby to Midway. Price data was last updated on March 30, 2025.

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Houston to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

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
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

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.
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

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 Hobby to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Our cheapest airline available from Houston Hobby Airport to Chicago Midway Airport is Southwest. Our recent data shows that you can find tickets from as low as $188 on this airline. An additional option worth looking into is Delta, starting at $217. You may be able to fly from Houston Hobby Airport to Chicago Midway Airport for 15% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Houston Hobby Airport to Chicago Midway Airport one-way?

    $90 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Allegiant Air and Delta, with prices starting from $103 and $109, respectively.

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

    Looking for the cheapest flight from Houston Hobby Airport to Chicago Midway Airport? While on average our users pay $257, our data indicates the cheapest price to be $88. The most popular route (Houston Hobby - Chicago Midway), is priced around $88.

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

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

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

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

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

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

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

Book flights to Houston Hobby Airport if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Hobby to Midway

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

Top 2 airlines flying from Hobby to Midway

Discover the top 2 airlines that operate flights from Hobby 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$144FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$190Average$339FlexibilityNo cancel feeOn-time63%

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