Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Houston to Chicago from $49

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 11/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Houston to Chicago

Cheap round-trip flights

Frontier Logo
6:09 pm - 8:46 pmIAH-MDW
2h 37mnonstop
Frontier Logo
6:30 am - 9:18 amMDW-IAH
2h 48mnonstop
$92Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
6:09 pm - 8:46 pmIAH-MDW
2h 37mnonstop
Frontier Logo
6:30 am - 9:18 amMDW-IAH
2h 48mnonstop
$93Frontier
Find Deal
Fri, Sep 26 - Thu, Oct 2
Frontier Logo
10:08 am - 12:46 pmIAH-MDW
2h 38mnonstop
Frontier Logo
6:30 am - 9:18 amMDW-IAH
2h 48mnonstop
$94Frontier
Find Deal
Sun, Sep 28 - Thu, Oct 2
Frontier Logo
6:09 pm - 8:46 pmIAH-MDW
2h 37mnonstop
Frontier Logo
2:26 pm - 5:14 pmMDW-IAH
2h 48mnonstop
$98Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Frontier Logo
1:39 pm - 4:09 pmIAH-MDW
2h 30mnonstop
Frontier Logo
9:44 am - 10:03 pmMDW-IAH
12h 19m1 stop
$108Frontier
Find Deal
Sat, Oct 18 - Mon, Oct 20
Multiple Airlines Logo
5:45 am - 1:38 pmIAH-MDW
7h 53m1 stop
Multiple Airlines Logo
9:00 am - 11:49 amMDW-IAH
2h 49mnonstop
$132Multiple Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 27
Southwest Logo
5:55 pm - 8:20 pmHOU-MDW
2h 25mnonstop
Southwest Logo
9:30 pm - 12:05 amMDW-HOU
2h 35mnonstop
$157Southwest
Find Deal
Sat, Oct 18 - Mon, Oct 20
Southwest Logo
11:10 am - 1:35 pmHOU-MDW
2h 25mnonstop
Southwest Logo
8:25 am - 12:30 pmMDW-HOU
4h 05m1 stop
$163Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
1:13 pm - 9:10 pmHOU-MDW
7h 57m1 stop
Delta Logo
12:48 pm - 5:48 pmMDW-HOU
5h 00m1 stop
$253Delta
Find Deal
Sat, Oct 4 - Mon, Oct 6
Delta Logo
2:22 pm - 10:14 pmHOU-MDW
7h 52m1 stop
Delta Logo
6:00 am - 1:27 pmMDW-HOU
7h 27m1 stop
$258Delta
Find Deal
Sat, Oct 11 - Sat, Oct 18

Frontier flights from Houston to Chicago Midway Airport

Our best Frontier deals on Houston to Chicago Midway Airport flight tickets
Frontier
Sep 26
IAH6:09 pmHouston George Bush Intcntl
2h 37m
MDW8:46 pmChicago Midway
Sep 28
MDW6:30 amChicago Midway
2h 48m
IAH9:18 amHouston George Bush Intcntl
$92
Find similar
Frontier
Sep 26
IAH6:09 pmHouston George Bush Intcntl
2h 37m
MDW8:46 pmChicago Midway
Oct 2
MDW6:30 amChicago Midway
2h 48m
IAH9:18 amHouston George Bush Intcntl
$93
Find similar
Frontier
Sep 28
IAH10:08 amHouston George Bush Intcntl
2h 38m
MDW12:46 pmChicago Midway
Oct 2
MDW6:30 amChicago Midway
2h 48m
IAH9:18 amHouston George Bush Intcntl
$94
Find similar

Southwest flights from Houston to Chicago Midway Airport

Our best Southwest deals on Houston to Chicago Midway Airport flight tickets
Southwest
Oct 18
HOU5:55 pmHouston Hobby
2h 25m
MDW8:20 pmChicago Midway
Oct 20
MDW9:30 pmChicago Midway
2h 35m
HOU12:05 amHouston Hobby
$157
Find similar
Southwest
Oct 22
HOU11:10 amHouston Hobby
2h 25m
MDW1:35 pmChicago Midway
Oct 25
MDW8:25 amChicago Midway
4h 05m
1 stop
HOU12:30 pmHouston Hobby
$163
Find similar
Southwest
Oct 18
HOU12:50 pmHouston Hobby
6h 15m
1 stop
MDW7:05 pmChicago Midway
Oct 20
MDW9:30 pmChicago Midway
2h 35m
HOU12:05 amHouston Hobby
$167
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 September 16, 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 9/26

6:09 pm-8:46 pm

Nonstop2h 37m

Chicago Midway

Sun 9/28

6:30 am-9:18 am

Nonstop2h 48m

$92

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 9/26

6:09 pm-8:46 pm

Nonstop2h 37m

Chicago Midway

Thu 10/2

6:30 am-9:18 am

Nonstop2h 48m

$93

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sun 9/28

10:08 am-12:46 pm

Nonstop2h 38m

Chicago Midway

Thu 10/2

6:30 am-9:18 am

Nonstop2h 48m

$94

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 10/3

6:09 pm-8:46 pm

Nonstop2h 37m

Chicago Midway

Mon 10/6

2:26 pm-5:14 pm

Nonstop2h 48m

$98

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 10/18

1:39 pm-4:09 pm

Nonstop2h 30m

Chicago Midway

Mon 10/20

9:44 am-10:03 pm

1 stop12h 19m

$108

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 10/15

5:45 am-1:38 pm

1 stop7h 53m

Chicago Midway

Mon 10/27

9:00 am-11:49 am

Nonstop2h 49m

$132

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/18

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

Mon 10/20

9:30 pm-12:05 am

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 10/22

11:10 am-1:35 pm

Nonstop2h 25m

Chicago Midway

Sat 10/25

8:25 am-12:30 pm

1 stop4h 05m

$163

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/4

1:13 pm-9:10 pm

1 stop7h 57m

Chicago Midway

Mon 10/6

12:48 pm-5:48 pm

1 stop5h 00m

$253

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/11

2:22 pm-10:14 pm

1 stop7h 52m

Chicago Midway

Sat 10/18

6:00 am-1:27 pm

1 stop7h 27m

$258

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Houston, with most prices found around $184. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Houston during the month October is also very affordable. Most momondo users find prices during this month for around $199.

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 $270. 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 $413.

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 $187 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $244. 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 $244 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 is only 1 cabin class 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

Fastest flight time

2h 20m

Direct flights

Every day
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 $81Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,957 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
Lansing
Portage
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 10/16
Thu 10/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago