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Everything you should know

Nonstop flights
You can fly direct with United Airlines, American Airlines and others. Average duration is 2h 47m.
Direct flights
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Direct flights
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Top routes
Cheapest • 54% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 93% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
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Good to know
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Top layover airports
Cheapest • Avg $205 (round-trip)
Shortest trip • 4h 58m (one-way)
Insights
Insights
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Expert advice
Flight Deals

Cheap Flights from Houston to Chicago

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

Recent round-trip flight deals from Houston to Chicago

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HO1  Johor Bahru Hallmark Regency Hotel-CHI Chicago All airports
941 mimulti-stop
Multiple Airlines Logo
CHI  Chicago All airports-HO1 Johor Bahru Hallmark Regency Hotel
941 mimulti-stop
Multiple Airlines
Booking Insights

Price, demand and travel trends for Houston to Chicago flights

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

What is the cheapest Houston to Chicago flight route?

Houston George Bush Intcntl Airport (IAH) to Chicago Midway Airport (MDW) is the cheapest Houston to Chicago route, averaging $192 round-trip. Other Houston to Chicago routes average $494, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Houston to Chicago. It’s 10% cheaper than the average day, while Monday is the most expensive, with prices 26% higher.

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

•January is the cheapest month to fly from Houston to Chicago at $172 round-trip.
•July ($303) and June ($298) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 76% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Houston to Chicago the cheapest?

Flights from Houston to Chicago are cheapest 12 weeks before departure. Booking in this window typically costs about 47% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Houston to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

John Walton

John Walton

Expert on IAH

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Key details for Houston to Chicago flights

Low season

February
Beat the crowds with an average 32% drop in travelers.
The most popular month to fly with an average 40% increase in travelers.

When to book flights from Houston to Chicago

Are your dates flexible? Find out the best times to travel from Houston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Houston to Chicago 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 Houston to Chicago?

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

    • Earliest: departs at 5:00 am and lands at 7:47 am
    • Latest: departs at 11:55 pm and lands at 2:42 am.

    The flight takes about 2h 47m.

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

    Four cabin classes are available on flights from Houston to Chicago:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How long is a flight from Houston to Chicago?

    A nonstop flight from Houston to Chicago takes 2h 47m, covering 941 miles.

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

    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 Houston to Chicago flight?

    Round-trip flights from Houston to Chicago range from $168 to $358, with an average of $253 over the past 12 months. Anything below $168 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 35% above the $253 route average. Book 12 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $205 round-trip via Raleigh-Durham (RDU), compared to $254 for nonstop.

  • How does on-time performance compare across airlines flying from Houston to Chicago?

    United Airlines is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on Houston to Chicago flights are:

    • United Airlines: 93% on time
    • American Airlines: 88% on time
    • Frontier: 81% on time

    Overall, flights on this route are punctual 85% of the time on average.

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

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

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

    Morning is the busiest departure period on Houston to Chicago flights, with 46% of flights leaving in that window. Evening departures account for 27%, afternoon flights for 23%, and night flights for 4%.

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

    Two airlines offer in-flight Wi-Fi on Houston to Chicago flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

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

    Flights from Houston to Chicago may depart from several airports in Houston area, including Houston Hobby (HOU) and Houston George Bush Intcntl (IAH), with arrivals available at Chicago area airports such as Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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

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

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

    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 Houston to Chicago route, 15% of flights were delayed in the past 3 months, with delays averaging 2h 29m.

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

    One-stop flights from Houston to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 49% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 31% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 7% of one-stop connections
    • Raleigh-Durham (RDU) - 5% of one-stop connections

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

    Yes. Flexible dates can save you up to 29% on flights from Houston to Chicago. Saturday is the cheapest departure day at $228 round-trip on average, while Monday is the most expensive at $320, a difference of $92.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Houston to Chicago?

    4 airlines operate flights between Houston and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest
    • Frontier

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

    Flying via Dallas/Fort Worth (DFW) gives the shortest average 1-stop total travel time at 4h 58m, compared with 5h 44m via Detroit Metropolitan Wayne County (DTW) and 6h via Chicago O'Hare Intl (ORD).

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

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

    Among airlines operating Houston to Chicago flights:

    • Frontier: offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • United Airlines: offers extra legroom; offers free seat selection
    • 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 Houston to Chicago flights?

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

    • Frontier: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • United Airlines: a cabin bag and a checked bag in Economy Class

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

Your guide to booking Houston to Chicago 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 Saturday departure and avoid flying on Monday. On this route, Saturday flights average $228, about $92 less than Monday fares (29% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 47% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Houston to Chicago trip for January. Fares historically average $172 round-trip in that month - typically $131 less than the most expensive month, which is July (based on the last 12 months).
  • For the best chance of arriving on time, fly with United Airlines. Over the past three months, 93% of United Airlines flights from Houston to Chicago arrived on time, slightly above the route average of 85%. When flights on this route arrive late, they're delayed by an average of 2h 29m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through Raleigh-Durham Airport (RDU) can be cheaper than flying direct. The cheapest layover option averages $205 round-trip on this route - about $49 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

Prefer to fly direct from Houston to Chicago?

 
Find which airlines fly direct from Houston to Chicago, which days they fly and book direct flights.

Direct departures

Houston to Chicago

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Chicago to Houston

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

More options for your flight from Houston to Chicago

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