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Cheap flights from Houston Hobby Airport to Chicago Midway Airport 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 Hobby Airport to Chicago Midway Airport departing on 12/11. 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 Hobby Airport to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Houston Hobby Airport 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 Hobby Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from Houston Hobby Airport 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 Hobby Airport to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:36 am - 12:17 amHOU-MDW
13h 41m1 stop
8:15 am - 5:26 pmMDW-HOU
9h 11m1 stop
$118Frontier
Find Deal
Mon, Jan 27 - Wed, Jan 29
6:16 pm - 12:13 amHOU-MDW
5h 57m1 stop
8:15 am - 5:26 pmMDW-HOU
9h 11m1 stop
$134Frontier
Find Deal
Wed, Dec 4 - Wed, Dec 11
10:36 am - 12:13 amHOU-MDW
13h 37m1 stop
8:15 am - 5:28 pmMDW-HOU
9h 13m1 stop
$138Frontier
Find Deal
Mon, Jan 13 - Wed, Jan 15
11:30 am - 1:55 pmHOU-MDW
2h 25mnonstop
1:40 pm - 4:30 pmMDW-HOU
2h 50mnonstop
$158Southwest
Find Deal
Sat, Jan 18 - Tue, Jan 21
10:36 am - 12:13 amHOU-MDW
13h 37m1 stop
7:15 am - 9:33 amMDW-HOU
26h 18m1 stop
$160Frontier
Find Deal
Mon, Dec 9 - Thu, Dec 12
6:55 am - 9:15 amHOU-MDW
2h 20mnonstop
8:30 am - 11:20 amMDW-HOU
2h 50mnonstop
$178Southwest
Find Deal
Tue, Jan 21 - Sun, Jan 26
5:55 am - 8:20 amHOU-MDW
2h 25mnonstop
5:20 am - 8:15 amMDW-HOU
2h 55mnonstop
$198Southwest
Find Deal
Fri, Jan 17 - Mon, Jan 20
5:00 pm - 10:20 pmHOU-MDW
5h 20m1 stop
10:57 am - 5:50 pmMDW-HOU
6h 53m1 stop
$216Delta
Find Deal
Sat, Jan 18 - Tue, Jan 21
4:48 pm - 10:06 pmHOU-MDW
5h 18m1 stop
10:38 am - 5:47 pmMDW-HOU
7h 09m1 stop
$228Delta
Find Deal
Sat, Dec 7 - Tue, Dec 10
6:00 am - 11:59 amHOU-MDW
5h 59m1 stop
12:44 pm - 5:50 pmMDW-HOU
5h 06m1 stop
$247Delta
Find Deal
Thu, Jan 30 - Sun, Feb 2
6:16 pm - 12:13 amHOU-MDW
5h 57m1 stop
$49Frontier
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Wed, Dec 11
6:18 pm - 12:13 amHOU-MDW
5h 55m1 stop
$53Frontier
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Wed, Jan 15
6:16 pm - 12:13 amHOU-MDW
5h 57m1 stop
$56Frontier
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Wed, Dec 11
10:36 am - 12:17 amHOU-MDW
13h 41m1 stop
$62Frontier
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Thu, Jan 16
6:16 pm - 12:17 amHOU-MDW
6h 01m1 stop
$63Frontier
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Sun, Jan 26
11:30 am - 1:55 pmHOU-MDW
2h 25mnonstop
$70Southwest
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Sat, Jan 18
6:55 am - 9:15 amHOU-MDW
2h 20mnonstop
$79Southwest
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Wed, Jan 8
6:00 am - 11:58 amHOU-MDW
5h 58m1 stop
$108Delta
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Wed, Dec 18
4:48 pm - 10:06 pmHOU-MDW
5h 18m1 stop
$128Delta
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Sat, Dec 7
10:57 am - 5:51 pmHOU-MDW
6h 54m1 stop
$192Avelo Airlines
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Sun, Jan 5
8:47 am - 2:24 pmHOU-MDW
5h 37m1 stop
12:45 pm - 7:38 pmMDW-HOU
6h 53m1 stop
$393Allegiant Air
Find Deal
Mon, Nov 25 - Wed, Nov 27
11:02 am - 6:01 pmHOU-MDW
6h 59m1 stop
12:45 pm - 7:38 pmMDW-HOU
6h 53m1 stop
Sun, Nov 24 - Wed, Nov 27
4:50 pm - 7:15 pmHOU-MDW
2h 25mnonstop
4:25 pm - 7:15 pmMDW-HOU
2h 50mnonstop
$583Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
2:55 pm - 6:50 pmHOU-MDW
3h 55m1 stop
4:25 pm - 7:15 pmMDW-HOU
2h 50mnonstop
$588Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
2:55 pm - 6:50 pmHOU-MDW
3h 55m1 stop
3:00 pm - 8:00 pmMDW-HOU
5h 00m1 stop
$612Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
5:25 am - 7:50 amHOU-MDW
2h 25mnonstop
8:50 pm - 12:55 amMDW-HOU
4h 05m1 stop
$622Southwest
Find Deal
Mon, Nov 25 - Sat, Dec 21
5:25 am - 7:50 amHOU-MDW
2h 25mnonstop
8:40 am - 2:10 pmMDW-HOU
5h 30m1 stop
$627Southwest
Find Deal
Fri, Nov 22 - Fri, Nov 29
1:02 pm - 5:54 pmHOU-MDW
4h 52m1 stop
6:00 am - 12:17 pmMDW-HOU
6h 17m1 stop
$692Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
2:19 pm - 1:40 pmHOU-MDW
23h 21m1 stop
9:48 pm - 1:28 pmMDW-HOU
15h 40m1 stop
$693Frontier
Find Deal
Sun, Nov 24 - Wed, Nov 27
6:00 am - 11:58 amHOU-MDW
5h 58m1 stop
3:19 pm - 10:54 pmMDW-HOU
7h 35m1 stop
$702Delta
Find Deal
Mon, Nov 25 - Wed, Nov 27
11:30 am - 1:55 pmHOU-MDW
2h 25mnonstop
1:40 pm - 4:30 pmMDW-HOU
2h 50mnonstop
$158Southwest
Find Deal
Sat, Jan 18 - Tue, Jan 21
6:55 am - 9:15 amHOU-MDW
2h 20mnonstop
8:30 am - 11:20 amMDW-HOU
2h 50mnonstop
$178Southwest
Find Deal
Tue, Jan 21 - Sun, Jan 26
8:25 pm - 10:45 pmHOU-MDW
2h 20mnonstop
8:40 pm - 11:25 pmMDW-HOU
2h 45mnonstop
$198Southwest
Find Deal
Fri, Jan 17 - Sun, Jan 19
5:20 am - 7:40 amHOU-MDW
2h 20mnonstop
5:35 pm - 8:25 pmMDW-HOU
2h 50mnonstop
$209Southwest
Find Deal
Fri, Feb 28 - Mon, Mar 3
6:50 am - 9:15 amHOU-MDW
2h 25mnonstop
7:55 pm - 10:40 pmMDW-HOU
2h 45mnonstop
$220Southwest
Find Deal
Wed, Dec 11 - Sat, Dec 14
6:50 am - 9:15 amHOU-MDW
2h 25mnonstop
5:45 am - 8:35 amMDW-HOU
2h 50mnonstop
$229Southwest
Find Deal
Wed, Dec 11 - Sun, Dec 15
8:20 pm - 10:40 pmHOU-MDW
2h 20mnonstop
2:50 pm - 5:40 pmMDW-HOU
2h 50mnonstop
$233Southwest
Find Deal
Mon, Jan 13 - Sat, Jan 18
7:45 pm - 10:10 pmHOU-MDW
2h 25mnonstop
1:40 pm - 4:30 pmMDW-HOU
2h 50mnonstop
$239Southwest
Find Deal
Sun, Mar 2 - Tue, Mar 4
6:50 am - 9:15 amHOU-MDW
2h 25mnonstop
5:45 am - 8:35 amMDW-HOU
2h 50mnonstop
$253Southwest
Find Deal
Wed, Dec 11 - Sun, Dec 15
3:50 pm - 6:15 pmHOU-MDW
2h 25mnonstop
8:50 pm - 11:35 pmMDW-HOU
2h 45mnonstop
$256Southwest
Find Deal
Tue, Dec 10 - Thu, Dec 12

Southwest flights from Houston Hobby Airport to Chicago Midway Airport

Our best Southwest deals on Houston Hobby Airport to Chicago Midway Airport flight tickets
Southwest
Jan 18
HOU11:30 amHouston Hobby
2h 25m
MDW1:55 pmChicago Midway
Jan 21
MDW1:40 pmChicago Midway
2h 50m
HOU4:30 pmHouston Hobby
Southwest
Jan 21
HOU6:55 amHouston Hobby
2h 20m
MDW9:15 amChicago Midway
Jan 26
MDW8:30 amChicago Midway
2h 50m
HOU11:20 amHouston Hobby
Southwest
Jan 17
HOU5:55 amHouston Hobby
2h 25m
MDW8:20 amChicago Midway
Jan 20
MDW5:20 amChicago Midway
2h 55m
HOU8:15 amHouston Hobby

Delta flights from Houston Hobby Airport to Chicago Midway Airport

Our best Delta deals on Houston Hobby Airport to Chicago Midway Airport flight tickets
Delta
Jan 18
HOU5:00 pmHouston Hobby
5h 20m
1 stop
MDW10:20 pmChicago Midway
Jan 21
MDW10:57 amChicago Midway
6h 53m
1 stop
HOU5:50 pmHouston Hobby
Delta
Dec 7
HOU4:48 pmHouston Hobby
5h 18m
1 stop
MDW10:06 pmChicago Midway
Dec 10
MDW10:38 amChicago Midway
7h 09m
1 stop
HOU5:47 pmHouston Hobby
Delta
Jan 30
HOU6:00 amHouston Hobby
5h 59m
1 stop
MDW11:59 amChicago Midway
Feb 2
MDW12:44 pmChicago Midway
5h 06m
1 stop
HOU5:50 pmHouston Hobby

See travel insights to Chicago from

How to get the cheapest flight ticket from Houston Hobby 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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Houston Hobby Airport, with most prices found around $123. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Houston Hobby Airport during the month June is also very affordable. Most momondo users find prices during this month for around $127.

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

According to our data, Sunday is the cheapest day to fly to Chicago Midway Airport from Houston Hobby Airport. The lowest ticket price found for a Sunday departure recently was $121. 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, Monday is the most expensive day to depart from Houston Hobby Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $293.

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

Flying to Chicago Midway Airport from Houston Hobby Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $145 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $199. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Houston Hobby to Chicago Midway flight route?

Fly from Houston Hobby to Chicago Midway for the best Houston Hobby - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

We recommend purchasing flights from Houston Hobby Airport to Chicago Midway Airport 60 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $217. In the past 72 hours, momondo users found flights from Houston Hobby Airport to Chicago Midway Airport for as low as $48.

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

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

Can stopping save me money on Houston Hobby Airport to Chicago Midway Airport flights?

You could potentially save up to 30% on your flight if you consider stops on a Houston Hobby Airport to Chicago Midway Airport flight.

How have Houston Hobby Airport to Chicago Midway Airport flight prices changed over time?

As of November 2024, prices for Houston Hobby Airport to Chicago Midway Airport flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from Houston Hobby Airport to Chicago Midway Airport

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

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

Best Price Found

$49

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Houston Hobby Airport in the past 72 hours is $49. The best round-trip flight deal from Houston Hobby Airport to Chicago Midway Airport found on momondo in the last 72 hours is $118.
The fastest flight from Houston Hobby Airport to Chicago Midway Airport takes 2h 20m
Direct flights go from Houston Hobby Airport to Chicago Midway Airport every day.

  • How far is Houston Hobby to Chicago Midway by plane?

    A flight from Houston Hobby to Chicago Midway will travel around 937.5 mi. A reasonable flight in good conditions will take 2h 20m.

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

    Prices for flights from Houston Hobby Airport to Chicago Midway Airport refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Houston Hobby 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 Hobby Airport to Chicago Midway Airport?

  • What is the most popular airline from Houston Hobby Airport to Chicago Midway Airport?


Best airlines flying from Houston Hobby Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Houston Hobby Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $66Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
SouthwestPriceFrom $190Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $237Free CancellationRating
8.0
8,755 reviews
Search Delta flights
  • Southwest Flights From Houston Hobby Airport to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Houston Hobby Airport to Chicago Midway Airport, operating 24 flights/week on average for this route. A good Southwest flight deal for Houston Hobby Airport to Chicago Midway Airport starts from $190 round-trip, up to an average price of $384. Our users have rated Southwest at 8.1/10.


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 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?

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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