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Cheap flights from Houston George Bush Intcntl Airport to Chicago from $58

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 George Bush Intcntl Airport to Chicago departing on 11/26. 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

Enter your travel dates to find the best prices.
Frontier Logo
10:04 am - 12:37 pmIAH-MDW
2h 33mnonstop
Frontier Logo
9:27 am - 9:33 amMDW-IAH
24h 06m1 stop
$98Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
8:07 pm - 10:39 pmIAH-MDW
26h 32m1 stop
Frontier Logo
2:01 pm - 5:08 pmMDW-IAH
3h 07mnonstop
$99Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:45 pm - 10:17 pmIAH-MDW
2h 32mnonstop
Frontier Logo
4:00 pm - 7:00 pmMDW-IAH
3h 00mnonstop
$103Frontier
Find Deal
Thu, Nov 20 - Mon, Nov 24
Frontier Logo
7:40 pm - 10:12 pmIAH-MDW
2h 32mnonstop
Frontier Logo
4:00 pm - 7:00 pmMDW-IAH
3h 00mnonstop
$104Frontier
Find Deal
Sat, Nov 22 - Thu, Nov 27
Frontier Logo
7:45 pm - 10:17 pmIAH-MDW
2h 32mnonstop
Frontier Logo
4:00 pm - 7:00 pmMDW-IAH
3h 00mnonstop
$105Frontier
Find Deal
Mon, Nov 24 - Thu, Nov 27
Frontier Logo
8:07 pm - 9:58 pmIAH-MDW
25h 51m1 stop
Frontier Logo
3:52 pm - 6:59 pmMDW-IAH
3h 07mnonstop
$108Frontier
Find Deal
Wed, Dec 10 - Mon, Dec 15
Frontier Logo
6:05 am - 6:08 pmIAH-MDW
12h 03m1 stop
Frontier Logo
6:15 am - 4:10 pmMDW-IAH
9h 55m1 stop
$110Frontier
Find Deal
Thu, Dec 4 - Thu, Dec 11
Frontier Logo
6:05 am - 6:08 pmIAH-MDW
12h 03m1 stop
Frontier Logo
12:18 pm - 12:31 amMDW-IAH
12h 13m1 stop
$111Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
7:45 pm - 10:17 pmIAH-MDW
2h 32mnonstop
Frontier Logo
2:49 pm - 8:53 pmMDW-IAH
6h 04m1 stop
$114Frontier
Find Deal
Wed, Nov 26 - Wed, Dec 3
Multiple Airlines Logo
10:04 am - 12:37 pmIAH-MDW
2h 33mnonstop
Multiple Airlines Logo
6:06 pm - 7:44 amMDW-IAH
37h 38m2 stops
$143Multiple Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17

Frontier flights from Houston George Bush Intcntl Airport to Chicago Midway Airport

Our best Frontier deals on Houston George Bush Intcntl Airport to Chicago Midway Airport flight tickets
Frontier
Nov 13
IAH10:04 amHouston George Bush Intcntl
2h 33m
MDW12:37 pmChicago Midway
Nov 17
MDW9:27 amChicago Midway
24h 06m
1 stop
IAH9:33 amHouston George Bush Intcntl
$98
Find similar
Frontier
Dec 4
IAH8:07 pmHouston George Bush Intcntl
26h 32m
1 stop
MDW10:39 pmChicago Midway
Dec 7
MDW2:01 pmChicago Midway
3h 07m
IAH5:08 pmHouston George Bush Intcntl
$99
Find similar
Frontier
Nov 20
IAH7:45 pmHouston George Bush Intcntl
2h 32m
MDW10:17 pmChicago Midway
Nov 24
MDW4:00 pmChicago Midway
3h 00m
IAH7:00 pmHouston George Bush Intcntl
$103
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Houston George Bush Intcntl 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 November 2, 2025.
Use the filters below to find and compare flights from Houston George Bush Intcntl Airport 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

Thu 11/13

10:04 am-12:37 pm

Nonstop2h 33m

Chicago Midway

Mon 11/17

9:27 am-9:33 am

1 stop24h 06m

$98

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 12/4

8:07 pm-10:39 pm

1 stop26h 32m

Chicago Midway

Sun 12/7

2:01 pm-5:08 pm

Nonstop3h 07m

$99

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 11/20

7:45 pm-10:17 pm

Nonstop2h 32m

Chicago Midway

Mon 11/24

4:00 pm-7:00 pm

Nonstop3h 00m

$103

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 11/22

7:40 pm-10:12 pm

Nonstop2h 32m

Chicago Midway

Thu 11/27

4:00 pm-7:00 pm

Nonstop3h 00m

$104

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Mon 11/24

7:45 pm-10:17 pm

Nonstop2h 32m

Chicago Midway

Thu 11/27

4:00 pm-7:00 pm

Nonstop3h 00m

$105

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 12/10

8:07 pm-9:58 pm

1 stop25h 51m

Chicago Midway

Mon 12/15

3:52 pm-6:59 pm

Nonstop3h 07m

$108

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 12/4

6:05 am-6:08 pm

1 stop12h 03m

Chicago Midway

Thu 12/11

6:15 am-4:10 pm

1 stop9h 55m

$110

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 12/4

6:05 am-6:08 pm

1 stop12h 03m

Chicago Midway

Mon 12/8

12:18 pm-12:31 am

1 stop12h 13m

$111

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 11/26

7:45 pm-10:17 pm

Nonstop2h 32m

Chicago Midway

Wed 12/3

2:49 pm-8:53 pm

1 stop6h 04m

$114

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 11/13

10:04 am-12:37 pm

Nonstop2h 33m

Chicago Midway

Mon 11/17

6:06 pm-7:44 am

2 stops37h 38m

$143

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 George Bush Intcntl 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 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 George Bush Intcntl Airport, with most prices found around $158. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Houston George Bush Intcntl Airport during the month November is also very affordable. Most momondo users find prices during this month for around $162.

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 George Bush Intcntl Airport. 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 George Bush Intcntl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $389.

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

Flying to Chicago Midway Airport from Houston George Bush Intcntl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $198 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $243. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Houston George Bush Intcntl to Chicago Midway flight route?

Fly from Houston George Bush Intcntl to Chicago Midway for the best Houston George Bush Intcntl - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Houston George Bush Intcntl 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 George Bush Intcntl Airport to Chicago Midway Airport flight prices changed over time?

As of November 2025, prices for Houston George Bush Intcntl Airport to Chicago Midway Airport flights are approximately 2% more expensive when compared to flights at the same time last year.

When to book flights from Houston George Bush Intcntl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Houston George Bush Intcntl 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 George Bush Intcntl Airport to Chicago Midway Airport (IAH to MDW) flight deals and tips

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

Best Price Found

$84

Fastest flight time

2h 31m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Houston George Bush Intcntl Airport in the past 72 hours is $84. The best round-trip flight deal from Houston George Bush Intcntl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $131.
The fastest flight from Houston George Bush Intcntl Airport to Chicago Midway Airport takes 2h 31m
Direct flights go from Houston George Bush Intcntl Airport to Chicago Midway Airport every day.
Search flight deals

  • How far is Houston George Bush Intcntl to Chicago Midway by plane?

    Houston George Bush Intcntl and Chicago Midway are 917.9 mi apart from one another. A reasonable flight in good conditions will take 2h 31m.

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

    Prices for flights from Houston George Bush Intcntl Airport to Chicago Midway Airport are refreshed on a daily basis.

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

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

  • What is the most popular airline from Houston George Bush Intcntl Airport to Chicago Midway Airport?

Best airlines flying from Houston George Bush Intcntl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Houston George Bush Intcntl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $89Free CancellationRating
5.8
3,117 reviews
Search Frontier flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,001 reviews
Search Delta flights

  • Frontier Flights From Houston George Bush Intcntl Airport to Chicago Midway Airport

    Frontier is one of the most popular airlines flying from Houston George Bush Intcntl Airport to Chicago Midway Airport, operating 2 flights/week on average for this route. A good Frontier flight deal for Houston George Bush Intcntl Airport to Chicago Midway Airport starts from $89 round-trip, up to an average price of $200. Our users have rated Frontier at 5.8/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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 allows you to filter the results for Houston to Chicago flights to just show those with flexible booking policies.

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.

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