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Cheap flights from Houston Hobby Airport to Chicago from $67

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Houston Hobby Airport to Chicago departing on 10/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Houston Hobby Airport to Chicago

Cheap round-trip flights

Southwest Logo
9:15 pm - 11:35 pmHOU-MDW
2h 20mnonstop
Southwest Logo
5:15 am - 7:50 amMDW-HOU
2h 35mnonstop
$133Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
9:15 pm - 11:35 pmHOU-MDW
2h 20mnonstop
Southwest Logo
12:40 pm - 4:55 pmMDW-HOU
4h 15m1 stop
$143Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
8:55 pm - 11:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:30 pm - 12:05 amMDW-HOU
2h 35mnonstop
$149Southwest
Find Deal
Tue, Sep 30 - Fri, Oct 3
Southwest Logo
11:35 am - 5:10 pmHOU-MDW
5h 35m1 stop
Southwest Logo
12:40 pm - 4:55 pmMDW-HOU
4h 15m1 stop
$153Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
12:45 pm - 4:50 pmHOU-MDW
4h 05m1 stop
Southwest Logo
5:35 pm - 8:10 pmMDW-HOU
2h 35mnonstop
$155Southwest
Find Deal
Wed, Oct 8 - Sat, Oct 11
Southwest Logo
9:50 pm - 12:10 amHOU-MDW
2h 20mnonstop
Southwest Logo
5:00 am - 11:15 amMDW-HOU
6h 15m1 stop
$159Southwest
Find Deal
Fri, Dec 12 - Tue, Dec 16
Southwest Logo
9:50 pm - 12:10 amHOU-MDW
2h 20mnonstop
Southwest Logo
10:15 am - 1:10 pmMDW-HOU
2h 55mnonstop
$161Southwest
Find Deal
Fri, Dec 12 - Tue, Dec 16
Southwest Logo
3:40 pm - 6:05 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:30 pm - 12:05 amMDW-HOU
2h 35mnonstop
$163Southwest
Find Deal
Tue, Oct 28 - Thu, Oct 30
Delta Logo
6:00 am - 11:48 amHOU-MDW
5h 48m1 stop
Delta Logo
4:25 pm - 10:37 pmMDW-HOU
6h 12m1 stop
$217Delta
Find Deal
Wed, Oct 1 - Sat, Oct 4
Delta Logo
6:53 pm - 11:32 pmHOU-MDW
4h 39m1 stop
Delta Logo
5:34 pm - 11:46 pmMDW-HOU
6h 12m1 stop
$233Delta
Find Deal
Mon, Nov 24 - Thu, Nov 27

Delta flights from Houston Hobby Airport to Chicago Midway Airport

Our best Delta deals on Houston Hobby Airport to Chicago Midway Airport flight tickets
Delta
Oct 1
HOU6:00 amHouston Hobby
5h 48m
1 stop
MDW11:48 amChicago Midway
Oct 4
MDW4:25 pmChicago Midway
6h 12m
1 stop
HOU10:37 pmHouston Hobby
$217
Find similar
Delta
Nov 24
HOU6:53 pmHouston Hobby
4h 39m
1 stop
MDW11:32 pmChicago Midway
Nov 27
MDW5:34 pmChicago Midway
6h 12m
1 stop
HOU11:46 pmHouston Hobby
$233
Find similar
Delta
Sep 17
HOU10:44 amHouston Hobby
6h 51m
1 stop
MDW5:35 pmChicago Midway
Sep 22
MDW12:43 pmChicago Midway
4h 57m
1 stop
HOU5:40 pmHouston Hobby
$337
Find similar

Southwest flights from Houston Hobby Airport to Chicago Midway Airport

Our best Southwest deals on Houston Hobby Airport to Chicago Midway Airport flight tickets
Southwest
Oct 7
HOU9:15 pmHouston Hobby
2h 20m
MDW11:35 pmChicago Midway
Oct 8
MDW5:15 amChicago Midway
2h 35m
HOU7:50 amHouston Hobby
$133
Find similar
Southwest
Oct 7
HOU9:15 pmHouston Hobby
2h 20m
MDW11:35 pmChicago Midway
Oct 8
MDW12:40 pmChicago Midway
4h 15m
1 stop
HOU4:55 pmHouston Hobby
$143
Find similar
Southwest
Sep 30
HOU8:55 pmHouston Hobby
2h 25m
MDW11:20 pmChicago Midway
Oct 3
MDW9:30 pmChicago Midway
2h 35m
HOU12:05 amHouston Hobby
$149
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Houston Hobby Airport to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated September 11, 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

Fly to

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 10/7

9:15 pm-11:35 pm

Nonstop2h 20m

Chicago Midway

Wed 10/8

5:15 am-7:50 am

Nonstop2h 35m

$133

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 10/7

9:15 pm-11:35 pm

Nonstop2h 20m

Chicago Midway

Wed 10/8

12:40 pm-4:55 pm

1 stop4h 15m

$143

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 9/30

8:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Fri 10/3

9:30 pm-12:05 am

Nonstop2h 35m

$149

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 10/7

11:35 am-5:10 pm

1 stop5h 35m

Chicago Midway

Wed 10/8

12:40 pm-4:55 pm

1 stop4h 15m

$153

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 10/8

12:45 pm-4:50 pm

1 stop4h 05m

Chicago Midway

Sat 10/11

5:35 pm-8:10 pm

Nonstop2h 35m

$155

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 12/12

9:50 pm-12:10 am

Nonstop2h 20m

Chicago Midway

Tue 12/16

5:00 am-11:15 am

1 stop6h 15m

$159

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 12/12

9:50 pm-12:10 am

Nonstop2h 20m

Chicago Midway

Tue 12/16

10:15 am-1:10 pm

Nonstop2h 55m

$161

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 10/28

3:40 pm-6:05 pm

Nonstop2h 25m

Chicago Midway

Thu 10/30

9:30 pm-12:05 am

Nonstop2h 35m

$163

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 10/1

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Sat 10/4

4:25 pm-10:37 pm

1 stop6h 12m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 11/24

6:53 pm-11:32 pm

1 stop4h 39m

Chicago Midway

Thu 11/27

5:34 pm-11:46 pm

1 stop6h 12m

$233

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Houston Hobby Airport to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Houston Hobby Airport and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Houston Hobby Airport, with most prices found around $177. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Houston Hobby Airport during the month October is also very affordable. Most momondo users find prices during this month for around $208.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Houston Hobby Airport. The lowest ticket price found for a Wednesday departure recently was $269. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Houston Hobby Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $413.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Houston Hobby Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $185 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $249. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Houston Hobby to Chicago Midway flight route?

Fly from Houston Hobby to Chicago Midway for the best Houston Hobby - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Houston Hobby Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $243 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Houston Hobby Airport for as low as $129 on momondo.

What cabin class options are available on Houston Hobby to Chicago Midway flights?

There is only 1 cabin class available to choose from on Houston Hobby to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Houston Hobby Airport to Chicago Midway Airport flight prices changed over time?

As of September 2025, prices for Houston Hobby Airport to Chicago Midway Airport flights are approximately 42% cheaper when compared to flights at the same time last year.

When to book flights from Houston Hobby Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Houston Hobby Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Houston Hobby Airport to Chicago Midway Airport (HOU to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Houston Hobby Airport to Chicago Midway Airport

Best Price Found

$173

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Houston Hobby Airport in the past 72 hours is $173. The best round-trip flight deal from Houston Hobby Airport to Chicago Midway Airport found on momondo in the last 72 hours is $246.
The fastest flight from Houston Hobby Airport to Chicago Midway Airport takes 2h 20m
Direct flights go from Houston Hobby Airport to Chicago Midway Airport every day.
Search flight deals

  • How far is Houston Hobby to Chicago Midway by plane?

    A flight from Houston Hobby to Chicago Midway will travel around 937.5 mi. A reasonable flight in good conditions will take 2h 20m.

  • When did momondo last update prices for flights from Houston Hobby Airport to Chicago Midway Airport?

    Prices for flights from Houston Hobby Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Houston Hobby Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Houston Hobby Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Houston Hobby Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Houston Hobby Airport to Chicago Midway Airport?

  • What is the most popular airline from Houston Hobby Airport to Chicago Midway Airport?

Best airlines flying from Houston Hobby Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Houston Hobby Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $84Free CancellationRating
5.8
3,177 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,248 reviews
Search Southwest flights

  • Southwest Flights From Houston Hobby Airport to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Houston Hobby Airport to Chicago Midway Airport, operating 39 flights/week on average for this route. A good Southwest flight deal for Houston Hobby Airport to Chicago Midway Airport starts from $177 round-trip, up to an average price of $283. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Portage
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Crown Point
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Houston to Chicago?

It is quick and easy to find Houston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Houston to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Houston with this policy.

How can momondo help me find flights from Houston to Chicago?

momondo helps you find the best flight between Houston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Houston to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Houston and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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