CHI - HOU

$90 Find Cheap Flights from Chicago to Houston Hobby Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hobby departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$180
Typical prices: $202-$354
Southwest
Thu 8/6Mon 8/10
MDW - HOU • Non-stop
Cheapest non-stop
$179
Typical prices: $259-$427
Southwest
Thu 8/6Mon 8/10
MDW - HOU • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 34m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
Top routes
MDW
-
HOU
Cheapest
MDW
-
HOU
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Southwest
Most punctual • 80% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 88% price drop
March
Most popular
Good to know
Good to know
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+1
Good to know
Good to know
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Hobby (CHI-HOU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hobby that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hobby

Thu, Aug 6 - Mon, Aug 10
Southwest Logo
5:25 am - 7:50 am
MDW
-
HOU
2h 25mnonstop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$180Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
Southwest Logo
5:45 pm - 8:10 pm
HOU
-
MDW
2h 25mnonstop
$185Southwest
Wed, Aug 5 - Wed, Aug 12
Southwest Logo
4:40 pm - 10:45 pm
MDW
-
HOU
6h 05m
1 stop
Southwest Logo
8:50 pm - 11:10 pm
HOU
-
MDW
2h 20mnonstop
$190Southwest
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
5:30 pm - 8:00 pm
MDW
-
HOU
2h 30mnonstop
Southwest Logo
11:30 am - 4:55 pm
HOU
-
MDW
5h 25m
2 stops
$191Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
Southwest Logo
2:40 pm - 7:45 pm
HOU
-
MDW
5h 05m
1 stop
$195Southwest
Mon, Aug 10 - Tue, Aug 11
Southwest Logo
2:50 pm - 8:05 pm
MDW
-
HOU
5h 15m
1 stop
Southwest Logo
2:45 pm - 5:10 pm
HOU
-
MDW
2h 25mnonstop
$196Southwest
Thu, Sep 17 - Thu, Sep 24
Delta Logo
8:05 am - 1:19 pm
ORD
-
HOU
5h 14m
1 stop
Delta Logo
5:26 pm - 11:59 pm
HOU
-
ORD
6h 33m
1 stop
$199Delta
Wed, Aug 12 - Tue, Aug 18
Delta Logo
5:10 pm - 10:05 pm
MDW
-
HOU
4h 55m
1 stop
Delta Logo
10:50 am - 4:15 pm
HOU
-
MDW
5h 25m
1 stop
$199Delta
Wed, Aug 5 - Wed, Aug 12
Southwest Logo
7:40 am - 1:45 pm
MDW
-
HOU
6h 05m
2 stops
Southwest Logo
11:25 am - 3:30 pm
HOU
-
MDW
4h 05m
1 stop
$200Southwest
Wed, Aug 12 - Tue, Aug 18
Delta Logo
6:59 am - 4:25 pm
ORD
-
HOU
9h 26m
2 stops
Delta Logo
1:13 pm - 6:49 pm
HOU
-
ORD
5h 36m
1 stop
$204Delta
Booking Insights

KAYAK's insights & trends for Chicago to Hobby flights

Get data-powered insights and trends into flights from Chicago to Hobby to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Houston Hobby Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Houston Hobby Airport departing in August.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Houston Hobby Airport costs $245 on the route between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Houston Hobby Airport?

The average price of all round-trip flights from Chicago to Houston Hobby Airport clicked on KAYAK for each day over the last 12 months.

For Chicago to Houston Hobby Airport, Thursday is the cheapest day to fly on average and Monday is the most expensive. Flying from Houston Hobby Airport back to Chicago, the best deals are generally found on Friday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago to Houston Hobby Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Houston Hobby Airport is September, where tickets cost $45 (return) on average. On the other hand, the most expensive months are July and January, where the average cost of round-trip tickets is $707 and $504 respectively.

Can I save money by flying with a layover from Chicago to Houston Hobby Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $387, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Houston Hobby Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Houston Hobby Airport, you should book around 3 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 32% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Chicago to Hobby

Are your dates flexible? Find out the best times to travel from Chicago to Hobby based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Houston Hobby Airport flights

  • Which accommodation options are available at Hobby Airport?

    Located 1 mile away from the airport are luxurious hotels like the Days Inn & Suites, the DoubleTree by Hilton, Hampton Inn, and Holiday Inn, which provide cozy accommodations. The hotels also offer complimentary shuttles.

  • Does O'Hare Airport have disabled-friendly amenities?

    O'Hare Airport accommodates the needs of those with special needs and disabilities by providing amenities like elevators, Braille, accessible parking spots at lots B, C, D, F. G, H with ramps and elevators close by, operator-assisted phones in T2, T3, and T5, and mobility assistance.

  • What kind of public transportation can I use to get to Midway Airport from downtown Chicago?

    There is a regular and affordable train service—the Orange Line—that transports travelers from Downtown Chicago to MDW. Orange-Line trains take between 20min and 25min to complete the journey and charge around $2.50.

  • Does Midway Airport have lounges?

    Midway Airport has only one lounge, the USO lounge in Concourse C, which is open to those actively serving in the military and their families free of charge. The cozy lounge is equipped with gaming stations, a kitchenette with complimentary refreshments, TVs, and reading materials.

  • What is the cheapest flight from Chicago to Houston Hobby Airport?

    In the last 5 days, the lowest price for a flight from Chicago to Houston Hobby Airport was $90 for a one-way ticket and $179 for a round-trip.

  • Do I need a passport to fly between Chicago and Houston Hobby Airport?

    A passport is not required to fly from Chicago to Houston Hobby Airport.

  • Which airports will I be using when flying from Chicago to Houston Hobby Airport?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Houston Hobby.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Houston Hobby Airport?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to Houston Hobby Airport flight route.

  • Which aircraft models fly most regularly from Chicago to Houston Hobby Airport?

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago to Houston Hobby Airport flight route.

  • Which airline alliances offer flights from Chicago to Houston Hobby Airport?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Houston Hobby Airport, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Houston Hobby Airport?

    There are nonstop flights from Chicago to Houston Hobby Airport on a daily basis.

  • Which is the best airline for flights from Chicago to Houston, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and United Airlines. With an average price for the route of $343 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $337 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Houston Hobby Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Houston Hobby Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Houston Hobby Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Houston Hobby Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Houston Hobby Airport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Houston Hobby Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Houston Hobby Airport from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Houston Hobby Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $173 or less one-way and $328 or less round-trip.
  • Travelers can get nonstop flights to Hobby Airport (HOU) from Midway Airport (MDW) with Southwest Airlines. O'Hare Airport (ORD), which serves as a hub for United and American Airlines, also operates nonstop flights to Hobby Airport through both airlines.
  • O'Hare Airport provides tranquil spaces in their sophisticated lounges to ensure travelers get some much-needed relaxation time before their flights. The United Airlines United Club, located in Terminal 2, is one such lounge that one can access by paying around $59.
  • If you choose to drive yourself to Midway Airport, you can leave your vehicle at one of the long-term parking lots. The economy lot, which you will find on the northwest side of the terminal, provides convenient and affordable long-term parking at a rate of about $15. Free shuttles are available from the parking lot.
  • Hobby Airport provides families with essential amenities to ensure they have a stress-free time while at the airport. There is a children's play area in the west concourse. The airport also has two mothers'rooms situated right next to Gate 46 and Gate 4.
  • Travelers arriving at Hobby Airport can find Metro bus 40, which stops right outside the arrivals area. The Metro bus takes approximately 60min to travel from Hobby Airport to downtown Houston. The standard fare for the one-way trip is around $1.25.
  • Midway Airport has plenty of paintings, exhibits, sculptures, and murals spread all over the airport to give travelers a one-of-a-kind traveling experience. On the Mezzanine level of Midway Airport is the hanging sculpture that poetically links human-made and natural aviation.
  • Taking the GO Airport shuttle is a convenient way to travel from O'Hare Airport to downtown Chicago. Only passengers with one suitcase of standard size and one hand luggage are allowed onboard the shuttle. The standard fare for the shuttle trip, which takes approximately 45min, is around $30.

Prefer to fly direct from Chicago to Houston Hobby Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Houston Hobby.
Find which airlines fly direct from Chicago to Houston Hobby Airport, which days they fly and book direct flights.

Direct departures

Chicago to Houston Hobby

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Houston Hobby to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Everything you need to know for your flight from Chicago to Hobby

Other airlines flying to Chicago

Flight deals from the most popular airlines with KAYAK users flying the route
Southwest flights from Chicago to Houston Hobby Airport