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$51+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Houston Hobby to Chicago Midway are usually found in August or June, booked 60 days in advance, depart on a Sunday or Saturday 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

August

Round-trip from

$108
(Frontier)

One-way from

$51
(Frontier)
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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High demand for flights, 46% potential price rise
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Best time to find cheap flights, 43% potential price drop
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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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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 November 20, 2024.

This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1310:36 amHOU - MDW
1 stop13h 37mFrontier
Sun 12/157:15 amMDW - HOU
1 stop26h 18mFrontier
Deal found 11/19$178
This Southwest deal was found by Cheapflights users on 11/20. 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 12/116:50 amHOU - MDW
Nonstop2h 25mSouthwest
Sat 12/147:55 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/20$220
This Delta deal was found by Cheapflights users on 11/20. 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 12/74:48 pmHOU - MDW
1 stop5h 18mDelta
Tue 12/106:00 amMDW - HOU
1 stop6h 29mDelta
Deal found 11/20$256
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/258:47 amHOU - MDW
1 stop5h 37mAllegiant Air
Wed 11/2712:45 pmMDW - HOU
1 stop6h 53mAllegiant Air
Deal found 11/18$371
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2411:02 amHOU - MDW
1 stop6h 59mMultiple Airlines
Wed 11/2712:45 pmMDW - HOU
1 stop6h 53mMultiple Airlines
Deal found 11/18$395

Find flights from Hobby to Midway within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 1/15

6:18 pm-12:13 am

1 stop5h 55m

Chicago Midway

Wed 1/22

8:15 am-5:26 pm

1 stop9h 11m

$108

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 1/16

5:55 am-8:20 am

Nonstop2h 25m

Chicago Midway

Sun 1/19

8:40 pm-11:25 pm

Nonstop2h 45m

$198

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 1/21

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Sun 1/26

10:57 am-5:50 pm

1 stop6h 53m

$216

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/11

6:16 pm-12:13 am

1 stop5h 57m

$51

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 1/8

6:55 am-9:15 am

Nonstop2h 20m

$79

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/18

6:00 am-11:58 am

1 stop5h 58m

$108

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 11/25

8:47 am-2:24 pm

1 stop5h 37m

$178

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 1/5

10:57 am-5:51 pm

1 stop6h 54m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Hobby to Midway

Get recent, data-driven insights about flights from Hobby to Midway including ideal travel times, pricing trends, and more.

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 November 15, 2024.

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 60 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, December is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $159). Flying from Houston Hobby Airport to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 November 20, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 10% on flights from Houston Hobby Airport to Chicago Midway Airport by exploring options for tickets in the evening.

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 November 20, 2024.
Peruse reviews from past customers who have flown with Delta, Frontier and Southwest 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
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 Frontier. Our recent data shows that you can find tickets from as low as $108 on this airline. Additional options worth looking into are Southwest and Delta, starting at $198 and $216 round-trip. You may be able to fly from Houston Hobby Airport to Chicago Midway Airport for 50% 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?

    $51 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $79 and $108, 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 $358, our data indicates the cheapest price to be $161. The most popular route (Houston Hobby - Chicago Midway), is priced around $122.

  • 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, December is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $159). Flying from Houston Hobby Airport to Chicago Midway Airport in July is currently the most expensive (average of $231). 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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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 3 airlines flying from Hobby to Midway

Discover the top 3 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$150FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$190Average$384FlexibilityNo cancel feeOn-time63%
DeltaCheapest$237Average$575FlexibilityNo cancel feeOn-timeN/A
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