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Cheap flights from Houston to Chicago from $39

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 2/25. 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 to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Houston to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Houston to Chicago.

Cheap last minute flights

Planning a quick getaway from Houston to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Houston to Chicago

Find recent round-trip train or bus tickets from Houston to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
9:09 pm - 12:04 pmIAH-ORD
14h 55m1 stop
7:46 pm - 8:38 amORD-IAH
12h 52m1 stop
$64Spirit Airlines
Find Deal
Tue, Nov 19 - Wed, Nov 20
8:21 pm - 10:52 pmIAH-MDW
2h 31mnonstop
12:15 pm - 3:01 pmMDW-IAH
2h 46mnonstop
$69Frontier
Find Deal
Wed, Nov 20 - Sat, Nov 23
8:22 pm - 10:53 pmIAH-MDW
2h 31mnonstop
4:45 pm - 7:31 pmMDW-IAH
2h 46mnonstop
$71Frontier
Find Deal
Tue, Nov 19 - Wed, Nov 20
9:33 am - 12:14 pmIAH-ORD
2h 41mnonstop
7:46 pm - 8:38 amORD-IAH
12h 52m1 stop
$76Spirit Airlines
Find Deal
Wed, Nov 20 - Wed, Nov 20
3:50 pm - 6:15 pmHOU-MDW
2h 25mnonstop
10:25 pm - 1:10 amMDW-HOU
2h 45mnonstop
$189Southwest
Find Deal
Tue, Dec 10 - Fri, Dec 13
2:25 pm - 7:05 pmHOU-MDW
4h 40m1 stop
7:00 am - 9:50 amMDW-HOU
2h 50mnonstop
$199Southwest
Find Deal
Mon, Nov 18 - Wed, Nov 20
10:16 am - 4:15 pmHOU-MDW
5h 59m1 stop
4:58 pm - 10:08 pmMDW-HOU
5h 10m1 stop
$216Delta
Find Deal
Wed, Dec 4 - Sat, Dec 7
5:30 am - 12:49 pmIAH-MDW
7h 19m1 stop
4:58 pm - 11:59 pmMDW-IAH
7h 01m1 stop
$216Delta
Find Deal
Wed, Dec 4 - Sat, Dec 7
6:02 am - 10:58 amHOU-ORD
4h 56m1 stop
6:45 pm - 11:55 pmORD-HOU
5h 10m1 stop
$256American Airlines
Find Deal
Sat, Nov 16 - Mon, Nov 18
6:02 am - 10:58 amHOU-ORD
4h 56m1 stop
5:00 am - 9:42 amORD-HOU
4h 42m1 stop
$276American Airlines
Find Deal
Sat, Nov 16 - Sun, Nov 17
11:22 am - 1:50 pmIAH-MDW
2h 28mnonstop
$39Frontier
Find Deal
Tue, Feb 25
3:51 pm - 6:22 pmIAH-MDW
2h 31mnonstop
$40Frontier
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Sat, Nov 23
10:35 am - 1:23 pmIAH-ORD
2h 48mnonstop
$48Spirit Airlines
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Thu, Nov 7
9:33 am - 12:14 pmIAH-ORD
2h 41mnonstop
$50Spirit Airlines
Find Deal
Wed, Nov 13
6:22 am - 9:14 amIAH-ORD
2h 52mnonstop
$79United Airlines
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Tue, Jan 21
6:50 am - 9:10 amHOU-MDW
2h 20mnonstop
$79Southwest
Find Deal
Sat, Feb 15
3:50 pm - 6:15 pmHOU-MDW
2h 25mnonstop
$80Southwest
Find Deal
Wed, Nov 20
9:59 am - 12:49 pmIAH-ORD
2h 50mnonstop
$99United Airlines
Find Deal
Thu, Jan 16
6:09 am - 8:49 amIAH-ORD
2h 40mnonstop
$157American Airlines
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Thu, Nov 14
5:06 am - 12:14 pmIAH-ORD
7h 08m1 stop
$158American Airlines
Find Deal
Fri, Feb 28
12:52 pm - 8:15 pmIAH-MDW
7h 23m1 stop
4:19 pm - 12:07 amMDW-IAH
7h 48m1 stop
$110Frontier
Find Deal
Wed, Oct 30 - Sat, Nov 2
3:24 pm - 11:53 pmIAH-MDW
8h 29m1 stop
6:20 am - 11:09 amMDW-IAH
4h 49m1 stop
$113Frontier
Find Deal
Sat, Nov 2 - Mon, Nov 4
1:46 pm - 12:30 amIAH-ORD
10h 44m1 stop
3:52 pm - 6:38 pmORD-IAH
2h 46mnonstop
Sat, Nov 2 - Mon, Nov 4
1:46 pm - 12:30 amIAH-ORD
10h 44m1 stop
3:52 pm - 6:38 pmORD-IAH
2h 46mnonstop
Sat, Nov 2 - Mon, Nov 4
1:46 pm - 12:30 amIAH-ORD
10h 44m1 stop
9:11 pm - 12:05 amORD-IAH
2h 54mnonstop
$144Spirit Airlines
Find Deal
Sat, Nov 2 - Sat, Nov 16
1:46 pm - 12:30 amIAH-ORD
10h 44m1 stop
9:11 pm - 12:05 amORD-IAH
2h 54mnonstop
$153Spirit Airlines
Find Deal
Sat, Nov 2 - Sat, Nov 9
5:25 am - 7:50 amHOU-MDW
2h 25mnonstop
7:00 am - 9:50 amMDW-HOU
2h 50mnonstop
$318Southwest
Find Deal
Sun, Nov 3 - Tue, Nov 5
5:25 am - 7:50 amHOU-MDW
2h 25mnonstop
3:25 pm - 9:30 pmMDW-HOU
6h 05m1 stop
$327Southwest
Find Deal
Sun, Nov 3 - Tue, Nov 5
5:55 am - 12:12 pmHOU-ORD
6h 17m1 stop
8:05 am - 3:51 pmORD-HOU
7h 46m1 stop
$336American Airlines
Find Deal
Sun, Nov 3 - Tue, Nov 5
4:30 pm - 8:58 pmHOU-ORD
4h 28m1 stop
8:05 am - 3:51 pmORD-HOU
7h 46m1 stop
$493American Airlines
Find Deal
Sat, Nov 2 - Tue, Nov 5
9:47 pm - 12:24 amIAH-ORD
2h 37mnonstop
6:56 pm - 9:53 pmORD-IAH
2h 57mnonstop
$79Spirit Airlines
Find Deal
Sat, Dec 7 - Tue, Dec 10
9:34 pm - 12:12 amIAH-ORD
2h 38mnonstop
6:56 pm - 9:53 pmORD-IAH
2h 57mnonstop
$80Spirit Airlines
Find Deal
Wed, Nov 20 - Tue, Dec 17
8:22 pm - 10:53 pmIAH-MDW
2h 31mnonstop
4:45 pm - 7:31 pmMDW-IAH
2h 46mnonstop
$81Frontier
Find Deal
Tue, Nov 19 - Wed, Nov 20
8:22 pm - 10:53 pmIAH-MDW
2h 31mnonstop
12:15 pm - 3:01 pmMDW-IAH
2h 46mnonstop
$92Frontier
Find Deal
Tue, Nov 19 - Sat, Nov 23
8:35 am - 11:25 amIAH-ORD
2h 50mnonstop
5:50 pm - 8:50 pmORD-IAH
3h 00mnonstop
$177United Airlines
Find Deal
Thu, Jan 16 - Sat, Jan 18
3:50 pm - 6:15 pmHOU-MDW
2h 25mnonstop
10:25 pm - 1:10 amMDW-HOU
2h 45mnonstop
$189Southwest
Find Deal
Tue, Dec 10 - Fri, Dec 13
6:35 pm - 9:00 pmHOU-MDW
2h 25mnonstop
6:10 am - 9:05 amMDW-HOU
2h 55mnonstop
$209Southwest
Find Deal
Mon, Dec 9 - Thu, Jan 9
5:13 pm - 7:55 pmIAH-ORD
2h 42mnonstop
5:50 pm - 8:47 pmORD-IAH
2h 57mnonstop
$248United Airlines
Find Deal
Sat, Dec 14 - Mon, Dec 16
2:14 pm - 4:55 pmIAH-ORD
2h 41mnonstop
8:35 pm - 11:28 pmORD-IAH
2h 53mnonstop
$253American Airlines
Find Deal
Wed, Nov 6 - Wed, Nov 13
6:10 am - 8:50 amIAH-ORD
2h 40mnonstop
8:35 pm - 11:27 pmORD-IAH
2h 52mnonstop
$283American Airlines
Find Deal
Wed, Nov 6 - Mon, Nov 11

Spirit Airlines flights from Houston to Chicago

Our best Spirit Airlines deals on Houston to Chicago flight tickets
Spirit Airlines
Nov 19
IAH9:09 pmHouston George Bush Intcntl
14h 55m
1 stop
ORD12:04 pmChicago O'Hare Intl
Nov 20
ORD7:46 pmChicago O'Hare Intl
12h 52m
1 stop
IAH8:38 amHouston George Bush Intcntl
Spirit Airlines
Nov 20
IAH9:33 amHouston George Bush Intcntl
2h 41m
ORD12:14 pmChicago O'Hare Intl
Nov 20
ORD7:46 pmChicago O'Hare Intl
12h 52m
1 stop
IAH8:38 amHouston George Bush Intcntl
Spirit Airlines
Jan 11
IAH8:36 pmHouston George Bush Intcntl
2h 44m
ORD11:20 pmChicago O'Hare Intl
Jan 14
ORD4:45 pmChicago O'Hare Intl
2h 56m
IAH7:41 pmHouston George Bush Intcntl

Delta flights from Houston to Chicago

Our best Delta deals on Houston to Chicago flight tickets
Delta
Dec 4
HOU4:51 pmHouston Hobby
7h 08m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 7
ORD9:25 amChicago O'Hare Intl
6h 38m
1 stop
HOU4:03 pmHouston Hobby
Delta
Nov 5
IAH12:57 pmHouston George Bush Intcntl
5h 32m
1 stop
MDW6:29 pmChicago Midway
Nov 16
MDW6:00 amChicago Midway
5h 19m
1 stop
IAH11:19 amHouston George Bush Intcntl

How to get the cheapest flight ticket from Houston to Chicago

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 from Houston to Chicago?

September. The cheapest time of year to fly to Chicago from Houston is September. Most expensive is March

What is the cheapest day to depart Houston for Chicago?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Monday

When is the cheapest time to fly from Houston to Chicago?

In the evening. Houston to Chicago flights are approximately 24% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago from Houston?

Frontier. Frontier, Spirit Airlines, and United Airlines are the most popular carriers operating from Houston to Chicago

What is the cheapest Houston to Chicago flight route?

Houston Hobby - Chicago O'Hare Intl. Fly from Houston Hobby to Chicago O'Hare Intl for the best Houston - Chicago flight prices

How far in advance should you book Houston to Chicago flights?

36 days before. The cheapest time to buy a flight from Houston to Chicago is approximately 36 days to departure

How many flights depart from Houston to Chicago on average per day?

As of October 2024, 3 flights take off from Houston and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 42% of daily flights taking off at noon.

How many flights depart from Houston to Chicago on average per week?

As of October 2024, 24 flights take off from Houston and land in Chicago each week. The most common flight departure day for this route is Monday, with 29% of weekly flights taking off on this day.

Can stopping save me money on Houston to Chicago flights?

No. A direct flight is the cheapest option for a flight between Houston to Chicago.

Cheap Houston to Chicago flight deals and tips

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

Best Price Found

$39

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Houston in the past 72 hours is $39. The best round-trip flight deal from Houston to Chicago found on momondo in the last 72 hours is $64.
The fastest flight from Houston to Chicago takes 2h 20m
Direct flights go from Houston to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Houston to Chicago by plane?

    A flight from Houston to Chicago will travel around 941.3 mi. 2h 20m is a normal flight duration for this route.

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

    Prices for flights from Houston to Chicago refresh daily.

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

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

    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.

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

    The required travel and health documents for your Chicago 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. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


Best airlines flying from Houston to Chicago

Compare and see reviews for airlines that fly from Houston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $43Free CancellationRating
6.1
3,585 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $66Free CancellationRating
6.3
8,196 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $138Free CancellationRating
7.4
9,249 reviews
Search United Airlines flights
American AirlinesPriceFrom $145Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $194Free CancellationRating
8.0
8,845 reviews
Search Delta flights
SouthwestPriceFrom $195Free CancellationRating
8.1
5,125 reviews
Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Houston to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Houston to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Houston.

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

Price alerts on flights to Chicago from Houston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago