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.

How often are flights from Houston to Chicago delayed?

About 16% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 125 minutes.

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 16% of flights being delayed.

How long is the flight from Houston Hobby Airport to Chicago Midway Airport?

Airlines like Southwest and Delta fly from Houston Hobby Airport to Chicago Midway Airport in about 2h 25m. The time it takes to get you to your destination can typically vary by up to 2h 53m. The distance between Houston Hobby Airport and Chicago Midway Airport is about 938 mi. This flight may include one or multiple stops.

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 $89 on this airline. An additional option worth looking into is Southwest, starting at $167. You may be able to fly from Houston Hobby Airport to Chicago Midway Airport for 63% less than the average price by searching for these airlines.

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.

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).

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 $306, our data indicates the cheapest price to be $48. The most popular route (Houston Hobby - Chicago Midway), is priced around $89.

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.

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.

$79+ Flights from Houston Hobby Airport to Chicago Midway Airport

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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 October, booked 90 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap 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 December 19, 2025.

Thu 12/252:35 pmHOU - MDW

Nonstop2h 25mSouthwest

Thu 1/110:00 amMDW - HOU

1 stop4h 40mSouthwest

Deal found 12/18

$177

Wed 12/318:45 amHOU - MDW

1 stop6h 10mSouthwest

Thu 1/110:00 amMDW - HOU

1 stop4h 40mSouthwest

Deal found 12/17

$212

Thu 12/253:00 pmHOU - MDW

1 stop4h 05mSouthwest

Wed 12/3110:00 amMDW - HOU

1 stop5h 00mSouthwest

Deal found 12/18

$222

Wed 12/243:00 pmHOU - MDW

1 stop4h 05mSouthwest

Tue 1/67:55 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 12/17

$227

Wed 12/241:15 pmHOU - MDW

1 stop5h 50mSouthwest

Thu 1/16:55 amMDW - HOU

Nonstop2h 40mSouthwest

Deal found 12/16

$237

Wed 12/316:00 amHOU - MDW

1 stop5h 15mSouthwest

Wed 12/312:10 pmMDW - HOU

1 stop5h 25mSouthwest

Deal found 12/18

$247

Wed 12/318:45 amHOU - MDW

1 stop6h 10mSouthwest

Tue 1/67:55 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 12/17

$252

Best flights from Hobby to Midway
Discover carefully curated flight deals from Hobby to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 19, 2025.

Tue 1/208:30 pmHOU - MDW

Nonstop2h 25mSouthwest

Wed 1/216:15 amMDW - HOU

Nonstop3h 00mSouthwest

Deal found 12/17

$157

Wed 2/115:04 pmHOU - MDW

1 stop5h 18mDelta

Sat 2/144:13 pmMDW - HOU

1 stop6h 15mDelta

Deal found 12/16

$197

Wed 1/2811:05 amHOU - MDW

Nonstop2h 25mSouthwest

Sat 1/318:20 amMDW - HOU

Nonstop3h 00mSouthwest

Deal found 12/18

$157

Wed 2/186:40 amHOU - MDW

Nonstop2h 25mSouthwest

Mon 2/238:30 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 12/18

$177

Sat 1/105:04 pmHOU - MDW

1 stop5h 03mDelta

Sat 1/314:30 pmMDW - HOU

1 stop6h 03mDelta

Deal found 12/17

$207

Sat 1/105:45 amHOU - MDW

1 stop4h 47mDelta

Tue 2/310:48 amMDW - HOU

1 stop5h 22mDelta

Deal found 12/17

$207

Fri 1/165:00 amHOU - MDW

Nonstop2h 25mSouthwest

Sun 1/188:55 amMDW - HOU

Nonstop2h 55mSouthwest

Deal found 12/18

$197

Fri 1/235:04 pmHOU - MDW

1 stop5h 18mDelta

Sat 1/244:30 pmMDW - HOU

1 stop6h 03mDelta

Deal found 12/17

$207

Sat 1/105:04 pmHOU - MDW

1 stop5h 03mDelta

Wed 2/410:46 amMDW - HOU

1 stop5h 24mDelta

Deal found 12/17

$207

Last-minute flights from Hobby to Midway
Discover last-minute flight deals from Hobby to Midway. Data last updated December 19, 2025 and is based on user searches.

Thu 12/252:35 pmHOU - MDW

Nonstop2h 25mSouthwest

Thu 1/110:00 amMDW - HOU

1 stop4h 40mSouthwest

Deal found 12/18

$177

Thu 12/253:00 pmHOU - MDW

1 stop4h 05mSouthwest

Wed 12/3110:00 amMDW - HOU

1 stop5h 00mSouthwest

Deal found 12/18

$222

Wed 12/318:45 amHOU - MDW

1 stop6h 10mSouthwest

Thu 1/110:00 amMDW - HOU

1 stop4h 40mSouthwest

Deal found 12/17

$212

Wed 1/75:04 pmHOU - MDW

1 stop5h 03mDelta

Sat 1/314:30 pmMDW - HOU

1 stop6h 03mDelta

Deal found 12/17

$207

Wed 1/78:30 pmHOU - MDW

Nonstop2h 25mSouthwest

Fri 1/96:15 amMDW - HOU

Nonstop3h 00mSouthwest

Deal found 12/16

$217

Wed 1/711:00 amHOU - MDW

2 stops5h 35mSouthwest

Mon 2/26:15 amMDW - HOU

Nonstop3h 00mSouthwest

Deal found 12/17

$232

Thu 1/85:04 pmHOU - MDW

1 stop5h 03mDelta

Tue 2/310:48 amMDW - HOU

1 stop5h 22mDelta

Deal found 12/17

$227

Thu 1/155:15 amHOU - MDW

1 stop5h 05mSouthwest

Sun 1/186:15 amMDW - HOU

Nonstop3h 00mSouthwest

Deal found 12/18

$235

Fri 1/168:15 pmHOU - MDW

Nonstop2h 25mSouthwest

Sun 1/188:55 amMDW - HOU

Nonstop2h 55mSouthwest

Deal found 12/18

$197

Mon 1/197:10 amHOU - MDW

1 stop5h 45mSouthwest

Wed 1/218:55 amMDW - HOU

Nonstop2h 55mSouthwest

Deal found 12/17

$228

Tue 1/208:30 pmHOU - MDW

Nonstop2h 25mSouthwest

Wed 1/216:15 amMDW - HOU

Nonstop3h 00mSouthwest

Deal found 12/17

$157

One-way flights from Hobby to Midway
Search for one-way flight options from Hobby to Midway. Find affordable one-way fares based on user searches. Data last updated December 19, 2025.

Wed 3/46:40 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 12/19

$79

Thu 12/252:35 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 12/18

$89

Tue 2/178:15 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 12/18

$90

Wed 1/145:45 amHOU - MDW

1 stop4h 42mDelta

Deal found 12/18

$109

Mon 1/126:40 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 12/18

$119

Thu 1/18:45 amHOU - MDW

1 stop6h 10mSouthwest

Deal found 12/18

$124

Tue 3/106:00 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 12/18

$127

Thu 1/155:45 amHOU - MDW

1 stop4h 42mDelta

Deal found 12/18

$129

Thu 3/55:05 amHOU - MDW

Nonstop2h 20mSouthwest

Deal found 12/18

$130

Wed 1/1411:00 amHOU - MDW

2 stops5h 35mSouthwest

Deal found 12/18

$134

Thu 2/263:35 pmHOU - MDW

1 stop5h 05mSouthwest

Deal found 12/18

$135

Find flight deals from Hobby to Midway

Most accurate provider	CheapOair 3 stars
Most trusted provider	CheapOair 3 stars
Round-trip from	$157 (Southwest)
One-way from	$79 (Southwest)
Popular in	December
Cheapest in	September
Average price	$390
Good round-trip deal	$272 or less
Good one-way deal	$149 or less

Provider with most accurate pricing for Houston Hobby-Chicago Midway flight deals.

Search Deals

Provider most trusted by Cheapflights users for Houston Hobby-Chicago Midway flights.

Search Deals

From Houston Hobby to Chicago Midway

Search Deals

One-way flight from Houston Hobby to Chicago Midway

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. 5% potential price decrease ($14 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Price to beat on a round-trip flight from Houston Hobby to Chicago Midway.

Search Deals

Price to beat on a one-way flight from Houston Hobby to Chicago Midway.

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Houston Hobby Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 1/20

8:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Wed 1/21

6:15 am-9:15 am

Nonstop3h 00m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 1/28

11:05 am-1:30 pm

Nonstop2h 25m

Chicago Midway

Sat 1/31

8:20 am-11:20 am

Nonstop3h 00m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 2/18

6:40 am-9:05 am

Nonstop2h 25m

Chicago Midway

Mon 2/23

8:30 pm-11:15 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 2/11

5:04 pm-10:22 pm

1 stop5h 18m

Chicago Midway

Sat 2/14

4:13 pm-10:28 pm

1 stop6h 15m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 1/16

5:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Sun 1/18

8:55 am-11:50 am

Nonstop2h 55m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/10

5:04 pm-10:07 pm

1 stop5h 03m

Chicago Midway

Sat 1/31

4:30 pm-10:33 pm

1 stop6h 03m

$207

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/10

5:45 am-10:32 am

1 stop4h 47m

Chicago Midway

Tue 2/3

10:48 am-4:10 pm

1 stop5h 22m

$207

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 1/23

5:04 pm-10:22 pm

1 stop5h 18m

Chicago Midway

Sat 1/24

4:30 pm-10:33 pm

1 stop6h 03m

$207

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 1/10

5:04 pm-10:07 pm

1 stop5h 03m

Chicago Midway

Wed 2/4

10:46 am-4:10 pm

1 stop5h 24m

$207

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 2/7

7:00 am-9:25 am

Nonstop2h 25m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 21 results

Compare providers for flights from Hobby to Midway

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hobby to Midway in December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars
CheapOair	Price Accuracy3 stars	Trust Score*3 stars
Mytrip	Price Accuracy3 stars	Trust Score*3 stars
JustAirTicket	Price 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 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?

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 December is currently the most expensive (average of $154). 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?

Unlike in the afternoon, when flights are generally more expensive, you can save up to 32% 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?

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.

The best insider tips for Houston Hobby Airport to Chicago Midway Airport flights

Cheapflights partnered with top experts to bring you the best recommendations for your Houston Hobby Airport to Chicago Midway Airport trip

Airports

HOU

HOU offers three types of parking: Valet, Garage, and Economy. Valet is convenient and not much more expensive than Garage.

MDW

Use the Orange Line for a quick, 30-minute ride from MDW to downtown Chicago, operating almost 24 hours a day.

Our travel experts

Ramsey Qubein

Expert on MDW

Scott Laird

Expert on HOU

Reviews of airlines servicing Midway

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.

Southwest

7.9

Good

4,252 reviews

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

7.9

Good

4,252 reviews

Southwest

7.9

Good

4,252 reviews

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.

Frontier

5.8

Fair

3,081 reviews

Southwest

7.9

Good

4,252 reviews

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

How long is the flight from Houston Hobby Airport to Chicago Midway Airport?
Airlines like Southwest and Delta fly from Houston Hobby Airport to Chicago Midway Airport in about 2h 25m. The time it takes to get you to your destination can typically vary by up to 2h 53m. The distance between Houston Hobby Airport and Chicago Midway Airport is about 938 mi. This flight may include one or multiple stops.
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 $89 on this airline. An additional option worth looking into is Southwest, starting at $167. You may be able to fly from Houston Hobby Airport to Chicago Midway Airport for 63% less than the average price by searching for these airlines.
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 $306, our data indicates the cheapest price to be $48. The most popular route (Houston Hobby - Chicago Midway), is priced around $89.
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, 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 December is currently the most expensive (average of $154). 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

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Top 2 airlines flying from Hobby to Midway

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$89	Average$193	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$168	Average$276	FlexibilityNo cancel fee	On-time63%

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$79+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Hobby to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Houston Hobby to Chicago Midway are usually found in September or October, booked 90 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap 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 December 19, 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 December 19, 2025.

Find flight deals from Hobby to Midway

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Cheapflights Fare Finder

Use the filters below to find and compare flights from Houston Hobby Airport to Chicago Midway Airport that are best for you.

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 December.

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.

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?

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

What is the cheapest time of day to fly from HOU to MDW?

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

How often are flights from Houston to Chicago delayed?

What is the most punctual flight time for Houston to Chicago flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Houston to Chicago flights?

The best insider tips for Houston Hobby Airport to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.

Cheapflights partnered with top experts to bring you the best recommendations for your Houston Hobby Airport to Chicago Midway Airport trip

Airports

HOU

MDW

Our travel experts

Reviews of airlines servicing Midway

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.

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.

How long is the flight from Houston Hobby Airport to Chicago Midway Airport?

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

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

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

How can I find direct flights from Hobby to Midway?

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

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

Traveling to a place near Chicago Midway Airport?

Browse thousands of different options on Cheapflights for your next trip

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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

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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 December 19, 2025.