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Cheap flights from Houston to Chicago from $55

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 1/8. 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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0 bags

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Frontier Logo
6:05 pm - 11:25 pmIAH-MDW
5h 20m1 stop
Frontier Logo
3:02 pm - 6:09 pmMDW-IAH
3h 07mnonstop
$98Frontier
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Fri, Feb 27 - Sun, Mar 1
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
6:05 am - 6:08 pmIAH-MDW
12h 03m1 stop
Frontier Logo
2:01 pm - 5:08 pmMDW-IAH
3h 07mnonstop
$100Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
11:49 am - 7:31 pmIAH-MDW
7h 42m1 stop
Frontier Logo
4:00 pm - 7:00 pmMDW-IAH
3h 00mnonstop
$101Frontier
Find Deal
Fri, Nov 21 - Thu, Nov 27
Southwest Logo
7:45 pm - 10:10 pmHOU-MDW
2h 25mnonstop
Southwest Logo
3:30 pm - 6:20 pmMDW-HOU
2h 50mnonstop
$117Southwest
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Wed, Dec 31 - Tue, Jan 6
Multiple Airlines Logo
8:47 pm - 12:41 pmIAH-MDW
15h 54m1 stop
Multiple Airlines Logo
4:00 pm - 7:00 pmMDW-IAH
3h 00mnonstop
$123Multiple Airlines
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Tue, Nov 18 - Thu, Nov 20
Southwest Logo
8:45 am - 2:10 pmHOU-MDW
5h 25m1 stop
Southwest Logo
3:30 pm - 6:20 pmMDW-HOU
2h 50mnonstop
$127Southwest
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Thu, Jan 1 - Tue, Jan 6
Multiple Airlines Logo
8:47 pm - 4:30 pmIAH-MDW
19h 43m2 stops
Multiple Airlines Logo
4:00 pm - 7:00 pmMDW-IAH
3h 00mnonstop
$130Multiple Airlines
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Wed, Nov 19 - Thu, Nov 27
Delta Logo
6:00 am - 11:55 amHOU-MDW
5h 55m1 stop
Delta Logo
11:05 am - 5:33 pmMDW-HOU
6h 28m1 stop
$198Delta
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Tue, Dec 2 - Sat, Dec 6
Delta Logo
6:00 am - 11:58 amHOU-MDW
5h 58m1 stop
Delta Logo
3:29 pm - 8:24 pmMDW-HOU
4h 55m1 stop
$216Delta
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Thu, Dec 18 - Wed, Dec 31

Frontier flights from Houston to Chicago Midway Airport

Our best Frontier deals on Houston to Chicago Midway Airport flight tickets
Frontier
Feb 27
IAH6:05 pmHouston George Bush Intcntl
5h 20m
1 stop
MDW11:25 pmChicago Midway
Mar 1
MDW3:02 pmChicago Midway
3h 07m
IAH6:09 pmHouston 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
Dec 4
IAH6:05 amHouston George Bush Intcntl
12h 03m
1 stop
MDW6:08 pmChicago Midway
Dec 7
MDW2:01 pmChicago Midway
3h 07m
IAH5:08 pmHouston George Bush Intcntl
$100
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Delta flights from Houston to Chicago Midway Airport

Our best Delta deals on Houston to Chicago Midway Airport flight tickets
Delta
Dec 2
HOU6:00 amHouston Hobby
5h 55m
1 stop
MDW11:55 amChicago Midway
Dec 6
MDW11:05 amChicago Midway
6h 28m
1 stop
HOU5:33 pmHouston Hobby
$198
Find similar
Delta
Dec 18
HOU6:00 amHouston Hobby
5h 58m
1 stop
MDW11:58 amChicago Midway
Dec 31
MDW3:29 pmChicago Midway
4h 55m
1 stop
HOU8:24 pmHouston Hobby
$216
Find similar
Delta
Nov 18
IAH11:05 amHouston George Bush Intcntl
7h 13m
1 stop
MDW6:18 pmChicago Midway
Nov 24
MDW5:34 pmChicago Midway
6h 23m
1 stop
IAH11:57 pmHouston George Bush Intcntl
$233
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 November 6, 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 2/27

6:05 pm-11:25 pm

1 stop5h 20m

Chicago Midway

Sun 3/1

3:02 pm-6:09 pm

Nonstop3h 07m

$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 12/4

6:05 am-6:08 pm

1 stop12h 03m

Chicago Midway

Sun 12/7

2:01 pm-5:08 pm

Nonstop3h 07m

$100

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 11/21

11:49 am-7:31 pm

1 stop7h 42m

Chicago Midway

Thu 11/27

4:00 pm-7:00 pm

Nonstop3h 00m

$101

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/31

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Tue 1/6

3:30 pm-6:20 pm

Nonstop2h 50m

$117

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Tue 11/18

8:47 pm-12:41 pm

1 stop15h 54m

Chicago Midway

Thu 11/20

4:00 pm-7:00 pm

Nonstop3h 00m

$123

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 1/1

8:45 am-2:10 pm

1 stop5h 25m

Chicago Midway

Tue 1/6

3:30 pm-6:20 pm

Nonstop2h 50m

$127

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 11/19

8:47 pm-4:30 pm

2 stops19h 43m

Chicago Midway

Thu 11/27

4:00 pm-7:00 pm

Nonstop3h 00m

$130

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 12/2

6:00 am-11:55 am

1 stop5h 55m

Chicago Midway

Sat 12/6

11:05 am-5:33 pm

1 stop6h 28m

$198

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 12/18

6:00 am-11:58 am

1 stop5h 58m

Chicago Midway

Wed 12/31

3:29 pm-8:24 pm

1 stop4h 55m

$216

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Houston, with most prices found around $182. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Houston during the month February is also very affordable. Most momondo users find prices during this month for around $213.

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 $387.

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 $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 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 $239 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.
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  • 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 $87Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
SouthwestPriceFrom $171Free CancellationRating
8.0
4,240 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,001 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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