CHI - HOU

$142 Find Cheap Flights from Chicago to Houston Hobby Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$283
Typical prices: $274-$427
Southwest
Mon 10/1Wed 10/31
MDW - HOU • Non-stop
Cheapest one-way
$142
Typical prices: $155-$297
Southwest
Wed 10/3
MDW - HOU • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 36m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 19 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $400 (round-trip)
Shortest trip • 4h 43m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Chicago to Hobby (CHI-HOU)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hobby

Thu, Oct 1 - Sat, Oct 31
Southwest Logo
9:30 pm - 12:05 amMDW  Chicago Midway-HOU Houston Hobby
2h 35mnonstop
Southwest Logo
10:15 am - 12:40 pmHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$283Southwest
Thu, Nov 26 - Tue, Dec 1
Southwest Logo
10:15 am - 12:50 pmMDW  Chicago Midway-HOU Houston Hobby
2h 35mnonstop
Southwest Logo
7:20 am - 9:50 amHOU  Houston Hobby-MDW Chicago Midway
2h 30mnonstop
$283Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
9:30 pm - 12:05 amMDW  Chicago Midway-HOU Houston Hobby
2h 35mnonstop
Southwest Logo
5:00 am - 7:25 amHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$283Southwest
Wed, Oct 14 - Thu, Oct 15
Southwest Logo
8:35 pm - 11:15 pmMDW  Chicago Midway-HOU Houston Hobby
2h 40mnonstop
Southwest Logo
7:55 pm - 10:20 pmHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$283Southwest
Thu, Oct 29 - Mon, Nov 2
American Airlines Logo
11:00 am - 4:36 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
5h 36m1 stop Dallas/Fort Worth
American Airlines Logo
5:02 pm - 10:30 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 28m1 stop Dallas/Fort Worth
$303American Airlines
Thu, Oct 29 - Mon, Nov 2
American Airlines Logo
9:40 am - 4:36 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
6h 56m1 stop Dallas/Fort Worth
American Airlines Logo
5:02 pm - 10:30 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 28m1 stop Dallas/Fort Worth
$303American Airlines
Wed, Oct 28 - Tue, Nov 3
Delta Logo
10:59 am - 4:33 pmMDW  Chicago Midway-HOU Houston Hobby
5h 34m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:28 pm - 10:33 pmHOU  Houston Hobby-MDW Chicago Midway
5h 05m1 stop Atlanta Hartsfield-Jackson
$303Delta
Wed, Oct 14 - Sat, Oct 17
Delta Logo
6:04 am - 2:07 pmMDW  Chicago Midway-HOU Houston Hobby
8h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:28 pm - 10:33 pmHOU  Houston Hobby-MDW Chicago Midway
5h 05m1 stop Atlanta Hartsfield-Jackson
$303Delta
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
7:09 am - 1:25 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
6h 16m1 stop Dallas/Fort Worth
American Airlines Logo
6:19 pm - 11:30 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 11m1 stop Dallas/Fort Worth
$303American Airlines
Thu, Oct 29 - Tue, Nov 3
Delta Logo
10:44 am - 4:33 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
5h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:12 am - 5:47 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 35m1 stop Atlanta Hartsfield-Jackson
$303Delta
Booking Insights

Price, demand and travel trends for Chicago to Houston Hobby Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago to Houston Hobby Airport with more confidence.

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

Round-trip flights from Chicago to Houston Hobby Airport start at $283. Prices are typical for this route right now, with typical round-trip fares ranging from $274 to $427. The lowest price found in the past 5 days was $283 on Southwest.

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

There's little price difference between Chicago to Houston Hobby Airport routes. They average around $349 round-trip, based on KAYAK data over the past 12 months.

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

Wednesday is the cheapest day of the week to fly from Chicago to Houston Hobby Airport, it is 17% cheaper than the average day. Sunday is the most expensive day with flight prices 26% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • January and September are the cheapest months to fly from Chicago to Houston Hobby Airport at $259 round-trip.
  • March ($392) and June ($382) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 51% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago to Houston Hobby Airport the cheapest?

Flights from Chicago to Houston Hobby Airport are cheapest 19 weeks before departure. Booking in this window typically costs about 45% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Chicago to Houston Hobby Airport flights

Low season

January

Cheapest flight

$142
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 6% 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

Your Chicago to Houston Hobby Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • Which airlines offer extra legroom and free seat selection on Chicago to Houston Hobby Airport flights?

    Among airlines operating Chicago to Houston Hobby Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago to Houston Hobby Airport?

    Only Southwest operates flights between Chicago and Houston Hobby Airport.

  • Which airports can I use when flying from Chicago to Houston Hobby Airport?

    Flights from Chicago to Houston Hobby Airport may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Houston Hobby (HOU).

  • Which airlines include bags at no extra cost on Chicago to Houston Hobby Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago to Houston Hobby Airport?

    Only Economy Class is available on flights from Chicago to Houston Hobby Airport.

  • How much can I save by taking a layover when flying from Chicago to Houston Hobby Airport?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $343 round-trip, compared to $400 via a layover through Atlanta Hartsfield-Jackson (ATL).

  • What is the standard checked-bag allowance on flights from Chicago to Houston Hobby Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Chicago to Houston Hobby Airport pass through?

    Connecting flights from Chicago to Houston Hobby Airport most commonly pass through:

    • Dallas Love Field (DAL) - 67% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 33% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

  • Can I save money by using flexible dates for flights from Chicago to Houston Hobby Airport?

    Yes. Being flexible with your travel dates can save you up to 34% on the Chicago to Houston Hobby Airport route. Wednesday is the cheapest departure day at $288 round-trip on average, while Sunday is the most expensive at $436, a difference of $148. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • At what point is a flight considered delayed from Chicago to Houston Hobby Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Houston Hobby Airport route, 20% of flights were delayed in the past 3 months, with delays averaging 1 hour 53 minutes.

  • How are flight departures from Chicago to Houston Hobby Airport spread across the day?

    Morning is the busiest departure period on Chicago to Houston Hobby Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 25%, evening flights for 25%, and night flights for 0%.

  • What popular places can I visit in Houston Hobby Airport?

    Some of the most popular sights in Houston Hobby Airport are Downtown Houston, George R. Brown Convention Center and Galleria Mall. These are among the most viewed places in Houston Hobby Airport on KAYAK.

  • What are the earliest and latest flights from Chicago to Houston Hobby Airport?

    These are the earliest and latest flight times available from Chicago to Houston Hobby Airport:

    • Earliest: departs at 5:05 am and lands at 7:41 am
    • Latest: departs at 11:05 pm and lands at 1:41 am.

    The flight takes about 2h 36m.

  • How expensive are last-minute Chicago to Houston Hobby Airport flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 26% above the route average of $345. Book 19 weeks before departure for the lowest fares.

  • How long is a flight from Chicago to Houston Hobby Airport?

    A nonstop flight from Chicago to Houston Hobby Airport takes 2h 36m, covering 946 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Chicago to Houston Hobby Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $283 to $1,779. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Chicago to Houston Hobby Airport looking right now?

    One-way fares from Chicago to Houston Hobby Airport are currently lower than usual. Average one-way flight prices are about $148, which is 33% below the typical average for this route.

  • How does Southwest’s on-time performance compare to other airlines on Chicago to Houston Hobby Airport flights?

    Southwest is the only airline operating Chicago to Houston Hobby Airport flights. 80% of its flights are on time.

  • How do delay rates compare for morning and evening flights from Chicago to Houston Hobby Airport?

    Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Chicago to Houston Hobby Airport?

    Flying via Dallas Love Field (DAL) gives the shortest average 1-stop total travel time at 4h 43m, compared with 5h 30m via Atlanta Hartsfield-Jackson (ATL).

  • What car rental options are available at Houston Hobby Airport (HOU)?

    Houston Hobby Airport (HOU) hosts 5 major car rental companies, with daily rates starting from around $20 for economy cars. Top options include:
    · Thrifty
    · Dollar
    · Alamo
    · Hertz
    · Budget

  • How much should I expect to pay for a Chicago to Houston Hobby Airport flight?

    Round-trip flights from Chicago to Houston Hobby Airport range from $274 to $427, with an average of $345 over the past 12 months. Anything below $274 counts as a good deal.

  • Which airlines offer Wi-Fi on Chicago to Houston Hobby Airport flights?

    JetBlue is the only airline on the Chicago to Houston Hobby Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Chicago to Houston Hobby Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $288 - about $148 less than Sunday (34% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 19 weeks before you fly. On this route, that window historically saves about 45% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to Houston Hobby Airport trip for January. Fares historically average $259 round-trip in that month - typically $133 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Houston Hobby Airport.
    - DoubleTree by Hilton Hotel Houston Hobby Airport
    - Best Western Plus Hobby Airport Inn & Suites
    - TownePlace Suites by Marriott Houston Hobby Airport
  • 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?

 
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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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Direct returns

Houston Hobby to Chicago

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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More options for your flight from Chicago to Hobby

Complete your trip to Houston with a hotel stay or car rental