HOU offers three types of parking: Valet, Garage, and Economy. Valet is convenient and not much more expensive than Garage.
$59+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Dec 4 — Dec 111
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Hobby to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Houston Hobby to Chicago Midway are usually found in September or February, booked 90 days in advance, depart on a Wednesday 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 4, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | May |
Cheapest in | September |
Average price | $228 |
Good round-trip deal | $208 or less |
Good one-way deal | $138 or less |
Find flight deals from Hobby to Midway
Cheapest flights from Hobby to MidwayExplore 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 4, 2025.
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 4, 2025.
This Southwest deal was found by Cheapflights users on 11/3. 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 12/107:00 amMDW - HOU
Nonstop2h 40mSouthwest
Deal found 11/3![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 11/3. 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 12/27:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 12/98:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/3![Southwest logo]()
$158
This Southwest deal was found by Cheapflights users on 11/2. 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 12/106:35 amHOU - MDW
Nonstop2h 25mSouthwest
Sun 12/145:10 amMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/2![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 11/3. 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 12/63:05 pmHOU - MDW
1 stop4h 00mSouthwest
Tue 12/910:15 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 11/3![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 11/2. 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 12/107:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Mon 12/156:20 amMDW - HOU
1 stop5h 05mSouthwest
Deal found 11/2![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 11/4. 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 12/47:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Mon 12/85:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/4![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 11/2. 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 12/63:05 pmHOU - MDW
1 stop4h 00mSouthwest
Sun 12/75:10 amMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/2![Southwest logo]()
$203
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 November 4, 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
Thu 1/29
6:40 am-9:05 am
Nonstop2h 25m
Chicago Midway
Sat 1/31
4:25 pm-7:15 pm
Nonstop2h 50m
$117
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 1/1
1:15 pm-5:15 pm
1 stop4h 00m
Chicago Midway
Tue 1/6
7:55 pm-10:40 pm
Nonstop2h 45m
$127
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 12/4
6:00 am-11:20 am
1 stop5h 20m
Chicago Midway
Sat 12/6
5:00 am-7:50 am
Nonstop2h 50m
$187
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 12/2
7:45 pm-10:10 pm
Nonstop2h 25m
Chicago Midway
Tue 12/9
5:35 am-10:15 am
1 stop4h 40m
$188
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 2/19
10:50 am-5:45 pm
1 stop6h 55m
Chicago Midway
Sat 2/21
4:13 pm-9:30 pm
1 stop5h 17m
$197
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 12/12
9:50 pm-12:10 am
Nonstop2h 20m
Chicago Midway
Sun 12/14
9:55 pm-12:35 am
Nonstop2h 40m
$197
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 12/4
7:45 pm-10:10 pm
Nonstop2h 25m
Chicago Midway
Mon 12/8
5:15 pm-8:00 pm
Nonstop2h 45m
$197
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 1/6
11:00 am-4:35 pm
2 stops5h 35m
Chicago Midway
Tue 1/27
3:30 pm-6:20 pm
Nonstop2h 50m
$198
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 2/19
9:55 am-2:30 pm
1 stop4h 35m
Chicago Midway
Sat 2/21
5:50 pm-8:40 pm
Nonstop2h 50m
$210
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 2/2
8:30 pm-10:55 pm
Nonstop2h 25m
$59
Showing 1-10 of 21 results
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago Midway Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Houston Hobby Airport-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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
Prices
Delays
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 October 31, 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, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $53). Flying from Houston Hobby Airport to Chicago Midway Airport in April is currently the most expensive (average of $142). 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 4, 2025.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 33% 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 November 2, 2025.
Travelers seeking maximum savings on their Houston Hobby Airport to Chicago Midway Airport flight should consider departing on Wednesday at noon 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.
How often are flights from Houston to Chicago delayed?
About 15% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 131 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 15% of flights being delayed.
The best insider tips for Houston Hobby 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 Hobby Airport to Chicago Midway Airport trip
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 4, 2025.
Peruse reviews from past customers who have flown with Southwest and Frontier from Houston Hobby Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
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.
Traveling to a place near Chicago Midway Airport?
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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.
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 November 4, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$87 | Average$181 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$171 | Average$281 | FlexibilityNo cancel fee | On-time63% |