CHI - HOU

$105 Find Cheap Flights from Chicago to Houston Hobby Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$209
Typical prices: $282-$442
Southwest
Mon 11/5Fri 11/9
MDW - HOU • Non-stop
Cheapest one-way
$105
Typical prices: $162-$282
Southwest
Mon 12/10
MDW - HOU • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 39m
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 48% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $364 (round-trip)
Shortest trip • 4h 37m (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

Wed, Nov 11 - Sat, Nov 14
Southwest Logo
8:50 pm - 11:30 pmMDW  Chicago Midway-HOU Houston Hobby
2h 40mnonstop
Southwest Logo
9:45 am - 12:10 pmHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$209Southwest
Sat, Nov 7 - Tue, Nov 10
Southwest Logo
6:20 pm - 9:10 pmMDW  Chicago Midway-HOU Houston Hobby
2h 50mnonstop
Southwest Logo
7:20 am - 9:50 amHOU  Houston Hobby-MDW Chicago Midway
2h 30mnonstop
$209Southwest
Thu, Oct 29 - Sat, Oct 31
Southwest Logo
9:30 pm - 12:10 amMDW  Chicago Midway-HOU Houston Hobby
2h 40mnonstop
Southwest Logo
6:00 am - 8:25 amHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$209Southwest
Thu, Jan 21 - Mon, Jan 25
Southwest Logo
5:25 am - 8:15 amMDW  Chicago Midway-HOU Houston Hobby
2h 50mnonstop
Southwest Logo
5:00 am - 7:25 amHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$209Southwest
Tue, Nov 3 - Wed, Nov 11
Delta Logo
11:39 am - 4:32 pmMDW  Chicago Midway-HOU Houston Hobby
4h 53m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:27 am - 4:18 pmHOU  Houston Hobby-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
$229Delta
Tue, Nov 10 - Wed, Nov 18
Delta Logo
11:27 am - 4:29 pmMDW  Chicago Midway-HOU Houston Hobby
5h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:59 amHOU  Houston Hobby-MDW Chicago Midway
5h 59m1 stop Atlanta Hartsfield-Jackson
$229Delta
Sat, Nov 7 - Tue, Nov 10
Delta Logo
3:40 pm - 11:03 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
7h 23m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:24 pm - 11:54 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
6h 30m1 stop Atlanta Hartsfield-Jackson
$229Delta
Thu, Dec 10 - Tue, Dec 15
Delta Logo
9:59 am - 4:29 pmORD  Chicago O'Hare Intl-HOU Houston Hobby
6h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:11 pm - 8:53 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 42m1 stop Atlanta Hartsfield-Jackson
$229Delta
Sat, Dec 12 - Mon, Dec 14
American Airlines Logo
6:00 am - 11:03 amORD  Chicago O'Hare Intl-HOU Houston Hobby
5h 03m1 stop Dallas/Fort Worth
American Airlines Logo
5:08 pm - 10:15 pmHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 07m1 stop Dallas/Fort Worth
$281American Airlines
Wed, Nov 4 - Wed, Nov 11
American Airlines Logo
6:00 am - 11:05 amORD  Chicago O'Hare Intl-HOU Houston Hobby
5h 05m1 stop Dallas/Fort Worth
American Airlines Logo
6:00 am - 11:02 amHOU  Houston Hobby-ORD Chicago O'Hare Intl
5h 02m1 stop Dallas/Fort Worth
$281American Airlines
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 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 typically range from $282 to $442. The lowest price found in the past 5 days was $209, 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 $357 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?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago to Houston Hobby Airport. It’s 15% cheaper than the average day, while Monday is the most expensive, with prices 26% higher.

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

•January is the cheapest month 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 flights 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 48% 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

$105
Beat the crowds with an average 51% drop in travelers.
The most popular month to fly with an average 40% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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 7:44 am
    • Latest: departs at 11:05 pm and lands at 1:44 am.

    The flight takes about 2h 39m.

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

    A nonstop flight from Chicago to Houston Hobby Airport takes 2h 39m, 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.

  • 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 $282 to $442, with an average of $361 over the past 12 months. Anything below $282 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 28% above the $361 route average. Book 19 weeks before departure for the lowest fares.

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

    On this route, nonstop and layover fares are close on average, with nonstop at $360 round-trip and layover options via Atlanta Hartsfield-Jackson (ATL) at $364.

  • 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.

  • 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 40% of flights leaving in that window. Afternoon departures account for 20%, evening flights for 20%, and night flights for 20%.

  • 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 $209 to $1,773. That means the highest observed fare was about 8x higher than the lowest one.

  • 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.

  • 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 $137, which is 39% below the typical average for this route.

  • 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 $25 for economy cars. Top options include:

    • Thrifty
    • Dollar
    • Alamo
    • Hertz
    • Ace

  • 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).

  • What time of day has the fewest delays on flights from Chicago to Houston Hobby Airport?

    Morning flights have the fewest delays on this route, while afternoon departures tend to have the most.

  • 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, 21% of flights were delayed in the past 3 months, with delays averaging 2h 06m.

  • 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:

    • Atlanta Hartsfield-Jackson (ATL) - 67% of one-stop connections
    • Dallas Love Field (DAL) - 33% of one-stop connections

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

    Yes. Flexible dates can save you up to 33% on flights from Chicago to Houston Hobby Airport. Wednesday is the cheapest departure day at $308 round-trip on average, while Monday is the most expensive at $458, a difference of $150.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago to Houston Hobby Airport?

    Only Southwest operates flights between Chicago and Houston Hobby Airport.

  • 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 37m, compared with 6h 05m via Atlanta Hartsfield-Jackson (ATL).

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

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

  • 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.

  • 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 always check the fare details before booking.

  • 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.

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 are flexible, aim for a Wednesday departure and avoid flying on Monday. On this route, Wednesday flights average $308, about $150 less than Monday fares (33% 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 48% 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).
  • For the best chance of arriving on time, fly with Southwest. Over the past three months, 80% of Southwest flights from Chicago to Houston Hobby Airport arrived on time, slightly above the route average of 79%. When flights on this route arrive late, they're delayed by an average of 2h 06m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Houston Hobby Airport.

    • Best Western Plus Hobby Airport Inn & Suites
    • DoubleTree by Hilton Hotel Houston Hobby Airport
    • Hilton Garden Inn 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

Southwest

Southwest

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Direct returns

Houston Hobby to Chicago

Monday

Southwest

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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