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Cheap flights from Houston to Chicago from $79

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 to Chicago departing on 8/30. 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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Cheap round-trip flights

Frontier Logo
11:36 am - 2:10 pmIAH-MDW
2h 34mnonstop
Frontier Logo
6:10 am - 4:39 pmMDW-IAH
10h 29m1 stop
$152Frontier
Find Deal
Fri, Aug 22 - Sat, Aug 23
Southwest Logo
1:35 pm - 4:00 pmHOU-MDW
2h 25mnonstop
Southwest Logo
7:20 pm - 9:50 pmMDW-HOU
2h 30mnonstop
$157Southwest
Find Deal
Sat, Sep 6 - Sat, Sep 6
Frontier Logo
7:01 pm - 8:22 amIAH-MDW
13h 21m1 stop
Frontier Logo
7:45 am - 10:34 amMDW-IAH
2h 49mnonstop
$158Frontier
Find Deal
Sat, Aug 23 - Mon, Aug 25
Frontier Logo
5:46 pm - 11:17 pmIAH-MDW
5h 31m1 stop
Frontier Logo
6:30 am - 9:18 amMDW-IAH
2h 48mnonstop
$159Frontier
Find Deal
Sat, Sep 6 - Sun, Sep 7
Frontier Logo
5:46 pm - 3:58 pmIAH-MDW
22h 12m1 stop
Frontier Logo
2:26 pm - 5:14 pmMDW-IAH
2h 48mnonstop
$161Frontier
Find Deal
Sat, Sep 6 - Mon, Sep 8
Frontier Logo
5:46 pm - 3:58 pmIAH-MDW
22h 12m1 stop
Frontier Logo
2:26 pm - 5:14 pmMDW-IAH
2h 48mnonstop
$162Frontier
Find Deal
Sat, Sep 6 - Mon, Sep 8
Southwest Logo
8:20 pm - 10:45 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW-HOU
2h 30mnonstop
$177Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
Delta Logo
10:22 am - 3:28 pmHOU-MDW
5h 06m1 stop
Delta Logo
4:25 pm - 10:31 pmMDW-HOU
6h 06m1 stop
$217Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
12:51 pm - 6:37 pmIAH-MDW
5h 46m1 stop
Delta Logo
1:08 pm - 5:51 pmMDW-IAH
4h 43m1 stop
$217Delta
Find Deal
Tue, Aug 26 - Wed, Aug 27
Delta Logo
1:05 pm - 5:47 pmHOU-MDW
4h 42m1 stop
Delta Logo
6:00 am - 12:10 pmMDW-HOU
6h 10m1 stop
$237Delta
Find Deal
Wed, Aug 20 - Wed, Aug 27

Frontier flights from Houston to Chicago Midway Airport

Our best Frontier deals on Houston to Chicago Midway Airport flight tickets
Frontier
Aug 22
IAH11:36 amHouston George Bush Intcntl
2h 34m
MDW2:10 pmChicago Midway
Aug 23
MDW6:10 amChicago Midway
10h 29m
1 stop
IAH4:39 pmHouston George Bush Intcntl
$152
Find similar
Frontier
Aug 23
IAH7:01 pmHouston George Bush Intcntl
13h 21m
1 stop
MDW8:22 amChicago Midway
Aug 25
MDW7:45 amChicago Midway
2h 49m
IAH10:34 amHouston George Bush Intcntl
$158
Find similar
Frontier
Sep 6
IAH5:46 pmHouston George Bush Intcntl
5h 31m
1 stop
MDW11:17 pmChicago Midway
Sep 7
MDW6:30 amChicago Midway
2h 48m
IAH9:18 amHouston George Bush Intcntl
$159
Find similar

Southwest flights from Houston to Chicago Midway Airport

Our best Southwest deals on Houston to Chicago Midway Airport flight tickets
Southwest
Sep 6
HOU1:35 pmHouston Hobby
2h 25m
MDW4:00 pmChicago Midway
Sep 6
MDW7:20 pmChicago Midway
2h 30m
HOU9:50 pmHouston Hobby
$157
Find similar
Southwest
Sep 6
HOU8:20 pmHouston Hobby
2h 25m
MDW10:45 pmChicago Midway
Sep 8
MDW8:45 pmChicago Midway
2h 30m
HOU11:15 pmHouston Hobby
$177
Find similar
Southwest
Aug 27
HOU8:55 pmHouston Hobby
2h 25m
MDW11:20 pmChicago Midway
Sep 3
MDW9:10 amChicago Midway
2h 35m
HOU11:45 amHouston Hobby
$187
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Houston 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 August 2, 2025.
Use the filters below to find and compare flights from Houston to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 8/22

11:36 am-2:10 pm

Nonstop2h 34m

Chicago Midway

Sat 8/23

6:10 am-4:39 pm

1 stop10h 29m

$152

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/6

1:35 pm-4:00 pm

Nonstop2h 25m

Chicago Midway

Sat 9/6

7:20 pm-9:50 pm

Nonstop2h 30m

$157

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 8/23

7:01 pm-8:22 am

1 stop13h 21m

Chicago Midway

Mon 8/25

7:45 am-10:34 am

Nonstop2h 49m

$158

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 9/6

5:46 pm-11:17 pm

1 stop5h 31m

Chicago Midway

Sun 9/7

6:30 am-9:18 am

Nonstop2h 48m

$159

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 9/6

5:46 pm-3:58 pm

1 stop22h 12m

Chicago Midway

Mon 9/8

2:26 pm-5:14 pm

Nonstop2h 48m

$161

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 9/6

5:46 pm-3:58 pm

1 stop22h 12m

Chicago Midway

Mon 9/8

2:26 pm-5:14 pm

Nonstop2h 48m

$162

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/6

8:20 pm-10:45 pm

Nonstop2h 25m

Chicago Midway

Mon 9/8

8:45 pm-11:15 pm

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 8/23

10:22 am-3:28 pm

1 stop5h 06m

Chicago Midway

Sat 8/30

4:25 pm-10:31 pm

1 stop6h 06m

$217

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Tue 8/26

12:51 pm-6:37 pm

1 stop5h 46m

Chicago Midway

Wed 8/27

1:08 pm-5:51 pm

1 stop4h 43m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 8/20

1:05 pm-5:47 pm

1 stop4h 42m

Chicago Midway

Wed 8/27

6:00 am-12:10 pm

1 stop6h 10m

$237

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 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 cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Houston, with most prices found around $157. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Houston during the month September is also very affordable. Most momondo users find prices during this month for around $168.

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. The lowest ticket price found for a Wednesday departure recently was $268. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $418.

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

Flying to Chicago Midway Airport from Houston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $174 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $236. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Houston to Chicago Midway flight route?

Fly from Houston George Bush Intcntl to Chicago Midway for the best Houston - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $236 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 for as low as $129 on momondo.

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

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

Cheap Houston to Chicago Midway Airport flight deals and tips

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

Best Price Found

$79

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Houston in the past 72 hours is $79. The best round-trip flight deal from Houston to Chicago Midway Airport found on momondo in the last 72 hours is $152.
The fastest flight from Houston to Chicago Midway Airport takes 2h 20m
Direct flights go from Houston to Chicago Midway Airport every day.
Search flight deals

  • How far is Houston to Chicago Midway by plane?

    Chicago Midway is 932.9 mi away from Houston. Typically, this will take 2h 20m by plane in normal conditions.

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

    Prices for flights from Houston to Chicago Midway Airport were last updated today.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Houston to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Houston to Chicago Midway Airport

Compare and see reviews for airlines that fly from Houston to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $74Free CancellationRating
5.8
3,241 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $196Free CancellationRating
8.0
7,983 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Houston to Chicago. momondo saves you time and could save you money on your trip.

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?

Once all potential Houston to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Houston to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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