HOU - CHI

₹ 10,409 Find Cheap Flights from Houston to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
₹ 20,725
Typical prices: ₹ 25,734-₹ 41,964
Southwest
Sun 9/12Wed 12/12
HOU - MDW • Direct
Cheapest one-way flight
₹ 10,409
Typical prices: ₹ 16,212-₹ 27,366
Southwest
Sun 16/12
HOU - MDW • Direct
Direct flights
You can fly direct with Southwest. Average duration is 2h 28m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 43% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 76% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 18 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 36% price drop
Most popular
Good to know
+1
Good to know
+1
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Booking Insights
Flight Deals

Cheap Flights from Houston to Chicago (HOU-CHI)

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

Recent return flight deals from Hobby to Chicago

Wed, 9 Dec - Sat, 12 Dec
Southwest Logo
07:20 - 09:50HOU  Houston Hobby-MDW Chicago Midway
2h 30mdirect
Southwest Logo
18:20 - 21:05MDW  Chicago Midway-HOU Houston Hobby
2h 45mdirect
₹ 20,725Southwest
Sat, 12 Dec - Wed, 16 Dec
Southwest Logo
05:00 - 07:25HOU  Houston Hobby-MDW Chicago Midway
2h 25mdirect
Southwest Logo
06:40 - 09:20MDW  Chicago Midway-HOU Houston Hobby
2h 40mdirect
₹ 21,475Southwest
Sat, 12 Dec - Wed, 16 Dec
Southwest Logo
08:50 - 12:55HOU  Houston Hobby-MDW Chicago Midway
4h 05m1 stop Kansas City
Southwest Logo
06:40 - 09:20MDW  Chicago Midway-HOU Houston Hobby
2h 40mdirect
₹ 22,038Southwest
Tue, 8 Dec - Tue, 15 Dec
Southwest Logo
07:30 - 12:05HOU  Houston Hobby-MDW Chicago Midway
4h 35m1 stop Lambert-St Louis
Southwest Logo
20:50 - 23:30MDW  Chicago Midway-HOU Houston Hobby
2h 40mdirect
₹ 22,413Southwest
Wed, 9 Dec - Sat, 12 Dec
Delta Logo
06:12 - 12:04HOU  Houston Hobby-MDW Chicago Midway
5h 52m1 stop Atlanta Hartsfield-Jackson
Delta Logo
16:08 - 23:31MDW  Chicago Midway-HOU Houston Hobby
7h 23m1 stop Atlanta Hartsfield-Jackson
₹ 22,600Delta
Wed, 9 Dec - Sat, 12 Dec
Delta Logo
17:27 - 22:54HOU  Houston Hobby-MDW Chicago Midway
5h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:39 - 23:31MDW  Chicago Midway-HOU Houston Hobby
10h 52m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
₹ 23,069Delta
Sat, 12 Dec - Wed, 16 Dec
Delta Logo
17:33 - 22:54HOU  Houston Hobby-MDW Chicago Midway
5h 21m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:28 - 16:29MDW  Chicago Midway-HOU Houston Hobby
5h 01m1 stop Atlanta Hartsfield-Jackson
₹ 23,351Delta
Tue, 8 Dec - Tue, 15 Dec
Delta Logo
06:12 - 16:50HOU  Houston Hobby-MDW Chicago Midway
10h 38m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
Delta Logo
11:28 - 16:29MDW  Chicago Midway-HOU Houston Hobby
5h 01m1 stop Atlanta Hartsfield-Jackson
₹ 23,820Delta
Mon, 7 Dec - Tue, 8 Dec
Southwest Logo
20:40 - 23:10HOU  Houston Hobby-MDW Chicago Midway
2h 30mdirect
Southwest Logo
10:15 - 12:50MDW  Chicago Midway-HOU Houston Hobby
2h 35mdirect
₹ 24,288Southwest
Sat, 12 Dec - Mon, 14 Dec
Southwest Logo
08:50 - 12:55HOU  Houston Hobby-MDW Chicago Midway
4h 05m1 stop Kansas City
Southwest Logo
06:40 - 09:20MDW  Chicago Midway-HOU Houston Hobby
2h 40mdirect
₹ 24,851Southwest
Booking Insights

Price, demand, and travel trends for Houston Hobby Airport to Chicago 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 return flight from Houston Hobby Airport to Chicago?

Return flights from Houston Hobby Airport to Chicago typically range from ₹ 25,734 to ₹ 41,964. The lowest price found in the past 5 days was ₹ 20,725 on Southwest.

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

Houston Hobby Airport (HOU) to Chicago Midway Airport (MDW) is the cheapest Houston Hobby Airport to Chicago route, averaging ₹ 33,126 return. Other Houston Hobby Airport to Chicago routes average ₹ 83,368, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Houston Hobby Airport 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 Hobby Airport to Chicago. It's 19% cheaper than the average day, while Sunday is the most expensive, with prices 18% higher.

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

•December is the cheapest month to fly from Houston Hobby Airport to Chicago at ₹ 21,288 return.
•July (₹ 36,573) and March (₹ 35,917) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 71% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from Houston Hobby Airport to Chicago are cheapest 18 weeks before departure. Booking in this window typically costs about 50% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Houston Hobby Airport to Chicago flights

Low season

January

Cheapest flight

₹ 10,409
Beat the crowds with an average 62% drop in travellers.
The most popular month to fly with an average 74% increase in travellers.
One-way flight from Houston Hobby Airport to Chicago Midway Airport

When to book flights from Hobby to Chicago

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

Your Houston Hobby Airport 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 Hobby Airport to Chicago?

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

    • Earliest: departs at 05:00 and lands at 07:28
    • Latest: departs at 22:40 and lands at 01:08.

    The flight takes about 2h 28m.

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

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

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

    A direct flight from Houston Hobby Airport to Chicago takes 2h 28m, covering 2,450 km.

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

    No, a passport is not required for this domestic route, but you will need another form of identification, such as a driving licence.

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

    Return flights from Houston Hobby Airport to Chicago range from ₹ 25,734 to ₹ 41,964, with an average of ₹ 33,185 over the past 12 months. Anything below ₹ 25,734 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 40% above the ₹ 33,185 route average. Book 18 weeks before departure for the lowest fares.

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

    On this route, direct flights are cheaper than stopover options on average. Direct fares average ₹ 33,046 return, compared with ₹ 35,908 via a stopover through Atlanta Hartsfield-Jackson (ATL).

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

    Southwest is the only airline operating Houston Hobby Airport to Chicago flights. 76% of its flights are on time.

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

    There is no standard. Checked bag policies vary by airline on this route. Most carriers charge ₹ 4,220–₹ 8,450 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 Hobby Airport to Chicago spread across the day?

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

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

    Yes. Based on fares seen in the past 5 days, return flight prices on this route showed a wide range, from about ₹ 20,725 to ₹ 174,408. That means the highest observed fare was about 8x higher than the lowest one.

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

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

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

    One-way fares from Houston Hobby Airport to Chicago are currently lower than usual. Average one-way flight prices are about ₹ 12,519, which is 40% below the typical average for this route.

  • 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 ₹ 5,915:

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

    Near Chicago Midway Airport (MDW) – daily rates from around ₹ 8,022:

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

    Near Chicago Greater Rockford Airport (RFD) – daily rates from around ₹ 7,638:

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

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

    Flights from Houston Hobby Airport to Chicago usually depart from Houston Hobby (HOU) and may arrive at several airports in Chicago area, including 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 Hobby Airport to Chicago?

    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 Houston Hobby Airport 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 Hobby Airport to Chicago route, 24% of flights were delayed in the past three months, with delays averaging 1h 53m.

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

    Most connecting flights from Houston Hobby Airport to Chicago pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route.

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

    Yes. Flexible dates can save you up to 31% on flights from Houston Hobby Airport to Chicago. Saturday is the cheapest departure day at ₹ 27,102 return on average, while Sunday is the most expensive at ₹ 39,199, a difference of ₹ 12,097.

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

  • Which airlines fly from Houston Hobby Airport to Chicago?

    Only Southwest operates flights between Houston Hobby Airport and Chicago.

  • What popular places can I visit in Chicago?

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

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

    Among airlines operating Houston Hobby Airport to Chicago 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 Houston Hobby Airport to Chicago 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

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

  • Do Chicago airports have accommodation?

    Travelers can relax and unwind at some of the luxury hotels located within Midway Airport, like Residence Inn Midway Airport hotel located just 1 mile away from the terminal. You can stay at the Hilton O'Hare Airport Hotel right across T1, T2, and T3.

  • Does Houston Hobby Airport have services for passengers with limited mobility?

    Those with limited mobility can receive baggage and wheelchair assistance from Skycap Service. The airport also has wheelchair-accessible restrooms and elevators. Those with disabilities should communicate any other assistance they may require through the airline before their departure date.

  • What family-friendly facilities do Chicago airports have?

    There is a nursing room on Concourse C at Midway Airport. Most restrooms at Midway Airport have baby-changing stations. You will also find kid-friendly restaurants at the airport. There is a kids'play area in Terminal 2 of O'Hare Airport. Nursing rooms are also available at Terminals 1 to 5.

  • Does Hobby Airport have affordable parking options?

    An affordable parking lot at Hobby Airport is the Ecopark, where you can leave your car for a fee of around $9. Another option is the Terminal Parking garage, which charges around $13 for the daily parking option. Valet parking is also available for around $28 per day.

Your guide to booking Houston Hobby Airport 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 Sunday. On this route, Saturday flights average ₹ 27,102, which is about ₹ 12,097 less than Sunday fares (31% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 18 weeks before you fly. On this route, that window historically saves about 50% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Houston Hobby Airport to Chicago trip for December. Fares historically average ₹ 21,288 return in that month – typically ₹ 15,286 less than the most expensive month, which is July (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
    • Skylark Motel Chicago Midway Airport
  • If you intend to fly from Houston's Hobby Airport (HOU) to Chicago's Midway Airport (MDW) without having layovers during the trip, you can get a flight operated by Southwest Airlines. If you do not mind a layover, you can use Delta Air Lines.
  • If you’re looking for a convenient transportation means from Downtown Houston to Hobby Airport, you should book the airport shuttles, which charge a minimum fare of around $19. The shuttles will drop you off outside the baggage claim. The cheaper alternative is the 73 Bellfort Metro, which charges around $1.25.
  • Several amenities at Chicago Midway Airport make traveling through the airport easier for those with limited mobility. Elevators have raised letters and braille, family assisted care restrooms, wheelchair-accessible telephone booths, and wheelchair escorts.
  • Exploring the vibrant Chicago city in a rental car will not only be convenient but will give you maximum flexibility. Midway Airport has several car rentals, like Enterprise, located on Level 2 of the airport's parking garage. The Avis desk is located on Level 3.
  • If you have plenty of time to kill before your flight, you can explore some of Hobby Airport's famous attractions, like the museum located at the airport's terminal, or marvel at the art deco design, which reflects Houston's Aviation era.
  • If you fly in from Houston, landing at Chicago Midway Airport provides more convenience than landing at the bustling O'Hare Airport (ORD). Because Midway is relatively smaller, you can expect shorter lines and faster service. Midway Airport is also closer to Downtown Chicago than O'Hare Airport.
  • From Chicago O'Hare Airport, you can board the Blue Line L train, which takes around 45min to reach Downtown Chicago. You can find the L Train, which charges a minimum rate of approximately $5 at either Terminal 1, Terminal 2, or Terminal 3.

Prefer to fly direct from Houston Hobby to Chicago?

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

Direct departures

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

Direct returns

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

More options for your flight from Hobby to Chicago

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