$87 Find Cheap Flights from Houston to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$143
Typical prices: $154-$342
Frontier
Thu 10/11Sun 10/14
IAH - ORD • Non-stop
Cheapest one-way
$87
Typical prices: $112-$246
Frontier
Sat 11/10
IAH - ORD • 1 stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and others. Average duration is 2h 47m.
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 57% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 92% 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 43% 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 $193 (round-trip)
Shortest trip • 4h 58m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
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

Sun, Oct 11 - Wed, Oct 14
Frontier Logo
11:36 am - 2:25 pmIAH  Houston George Bush Intcntl-ORD Chicago O'Hare Intl
2h 49mnonstop
Frontier Logo
7:40 am - 10:39 amORD  Chicago O'Hare Intl-IAH Houston George Bush Intcntl
2h 59mnonstop
$143Frontier
Wed, Oct 28 - Wed, Nov 4
Frontier Logo
6:05 am - 6:16 pmIAH  Houston George Bush Intcntl-ORD Chicago O'Hare Intl
12h 11m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:11 pm - 5:21 pmORD  Chicago O'Hare Intl-IAH Houston George Bush Intcntl
3h 10mnonstop
$143Frontier
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:14 am - 8:50 amIAH  Houston George Bush Intcntl-RFD Chicago Greater Rockford
24h 36m1 stop Fort Lauderdale
Multiple Airlines Logo
10:20 am - 7:19 amRFD  Chicago Greater Rockford-IAH Houston George Bush Intcntl
20h 59m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$212Multiple Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:14 am - 8:50 amIAH  Houston George Bush Intcntl-RFD Chicago Greater Rockford
24h 36m1 stop Fort Lauderdale
Multiple Airlines Logo
10:20 am - 7:19 amRFD  Chicago Greater Rockford-IAH Houston George Bush Intcntl
20h 59m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$213Multiple Airlines
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
6:35 pm - 9:05 pmHOU  Houston Hobby-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
8:05 am - 1:15 pmMDW  Chicago Midway-HOU Houston Hobby
5h 10m1 stop Louisville Intl
$220Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
7:05 am - 9:30 amHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
2:20 pm - 9:00 pmMDW  Chicago Midway-HOU Houston Hobby
6h 40m2 stops Omaha Eppley Airfield Dallas Love Field
$225Southwest
Thu, Jan 28 - Tue, Feb 2
United Airlines Logo
9:45 am - 4:20 pmIAH  Houston George Bush Intcntl-ORD Chicago O'Hare Intl
6h 35m1 stop San Antonio
United Airlines Logo
10:30 am - 1:32 pmORD  Chicago O'Hare Intl-IAH Houston George Bush Intcntl
3h 02mnonstop
$262United Airlines
Wed, Oct 21 - Wed, Oct 21
United Airlines Logo
6:15 am - 9:09 amIAH  Houston George Bush Intcntl-ORD Chicago O'Hare Intl
2h 54mnonstop
United Airlines Logo
6:29 pm - 9:20 pmORD  Chicago O'Hare Intl-IAH Houston George Bush Intcntl
2h 51mnonstop
$283United Airlines
Sat, Oct 24 - Sat, Oct 24
American Airlines Logo
7:34 am - 10:30 amIAH  Houston George Bush Intcntl-ORD Chicago O'Hare Intl
2h 56mnonstop
American Airlines Logo
3:13 pm - 6:07 pmORD  Chicago O'Hare Intl-IAH Houston George Bush Intcntl
2h 54mnonstop
$283American Airlines
Tue, Oct 27 - Sat, Nov 7
American Airlines Logo
7:34 am - 10:30 amIAH  Houston George Bush Intcntl-ORD Chicago O'Hare Intl
2h 56mnonstop
American Airlines Logo
9:05 pm - 11:57 pmORD  Chicago O'Hare Intl-IAH Houston George Bush Intcntl
2h 52mnonstop
$283American 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 from Houston to Chicago with more confidence.

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

Round-trip flights from Houston to Chicago start at $143. Prices are below average for this route right now, with typical round-trip fares ranging from $154 to $342. The lowest price found in the past 5 days was $143 on Frontier.

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 $175 round-trip. Other Houston to Chicago routes average $485, based on KAYAK data over the past 12 months.

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

Saturday is the cheapest day of the week to fly from Houston to Chicago, it is 7% cheaper than the average day. Monday 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 Houston to Chicago?

  • January is the cheapest month to fly from Houston to Chicago at $171 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 77% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Houston to Chicago the cheapest?

Flights from Houston to Chicago are cheapest 12 weeks before departure. Booking in this window typically costs about 43% 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

Cheapest flight

$87
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Houston George Bush Intcntl Airport to Chicago O'Hare Intl Airport

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

  • 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
    • United Airlines: offers extra legroom; offers free seat selection
    • American 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.

  • What airlines are available 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

  • 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).

  • 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
    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy 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 Houston to Chicago?

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

    • Economy Class
    • Business Class
    • First Class

  • 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 $193 round-trip via Las Vegas Harry Reid Intl (LAS), compared to $239 for nonstop.

  • 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 $32–$100 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 Houston to Chicago pass through?

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

    • Atlanta Hartsfield-Jackson (ATL) - 54% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 25% of one-stop connections
    • Raleigh-Durham (RDU) - 7% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 5% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

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

    On the Houston to Chicago route, being flexible with your departure day can save you up to 26%. Saturday is the cheapest day at $221 round-trip on average, while Monday is the most expensive at $298: a $77 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • 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 2 hours 29 minutes.

  • 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 29%, afternoon flights for 21%, and night flights for 4%.

  • What popular places can I visit in Chicago?

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

  • 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.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 31% above the route average of $236. Book 12 weeks before departure for the lowest fares.

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

    One-way fares from Houston to Chicago are currently lower than usual. Average one-way flight prices are about $118, which is 33% below the typical average for this route.

  • How does United Airlines’s on-time performance compare to other airlines on Houston to Chicago flights?

    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: 92% on time
    • American Airlines: 87% on time
    • Frontier: 81% on time

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

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

    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 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 00m via Chicago O'Hare Intl (ORD).

  • 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
    • Dollar
    • Ace

    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 $30:

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

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

    Round-trip flights from Houston to Chicago range from $154 to $342, with an average of $236 over the past 12 months. Anything below $154 counts as a good deal.

  • 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.

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 can be flexible, aim for a Saturday departure instead of Monday. On this route, Saturday flights average $221 - about $77 less than Monday (26% 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 43% 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 $171 round-trip in that month - typically $132 less than the most expensive month, which is July (based on the last 12 months).
  • If arriving on time is high on your priority list, United Airlines is the strongest pick on this route. 92% of United Airlines flights from Houston to Chicago arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 85%. When flights on this route do arrive late, the average delay is 2 hours 29 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • If you have the time, taking a 1-stop flight through Las Vegas Harry Reid Intl Airport (LAS) can be cheaper than flying direct. The cheapest layover option averages $193 round-trip on this route - about $46 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