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Cheap flight tickets from Chicago to Houston Hobby

Compare Chicago to Houston Hobby flight deals

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Flight deals from Chicago to Houston Hobby Airport

Looking for a cheap last-minute deal or the best return flight from Chicago to Houston Hobby Airport? If you want to travel next month, return fares start from RM762. Find the lowest prices on one-way and return tickets right here.
Houston.RM762 per passenger.Departing Sat, 25 Apr, returning Wed, 29 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 25 Apr, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Wed, 29 Apr, arriving in Chicago Midway.Price includes taxes and charges.From RM762, select.
Houston.RM770 per passenger.Departing Wed, 13 May, returning Sat, 16 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 13 May, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 16 May, arriving in Chicago Midway.Price includes taxes and charges.From RM770, select.
Houston.RM852 per passenger.Departing Wed, 29 Apr, returning Tue, 5 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Wed, 29 Apr, arriving in Houston Hobby.Inbound indirect flight with Southwest Airlines, departs from Houston Hobby on Tue, 5 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM852, select.
Houston.RM932 per passenger.Departing Thu, 30 Apr, returning Mon, 4 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 30 Apr, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 4 May, arriving in Chicago Midway.Price includes taxes and charges.From RM932, select.
Houston.RM1,038 per passenger.Departing Tue, 31 Mar, returning Tue, 28 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 31 Mar, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 28 Apr, arriving in Chicago Midway.Price includes taxes and charges.From RM1,038, select.
Houston.RM1,040 per passenger.Departing Fri, 14 Aug, returning Sat, 22 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 14 Aug, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 22 Aug, arriving in Chicago Midway.Price includes taxes and charges.From RM1,040, select.
Houston.RM1,046 per passenger.Departing Tue, 2 Jun, returning Sat, 6 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Jun, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Sat, 6 Jun, arriving in Chicago Midway.Price includes taxes and charges.From RM1,046, select.
Houston.RM1,079 per passenger.Departing Thu, 9 Jul, returning Tue, 14 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 9 Jul, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 14 Jul, arriving in Chicago Midway.Price includes taxes and charges.From RM1,079, select.
Houston.RM1,098 per passenger.Departing Wed, 27 May, returning Tue, 2 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 27 May, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Tue, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From RM1,098, select.
Houston.RM1,118 per passenger.Departing Fri, 31 Jul, returning Mon, 3 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 31 Jul, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Mon, 3 Aug, arriving in Chicago Midway.Price includes taxes and charges.From RM1,118, select.
Houston.RM1,288 per passenger.Departing Mon, 30 Mar, returning Tue, 31 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 30 Mar, arriving in Houston Hobby.Inbound indirect flight with Southwest Airlines, departs from Houston Hobby on Tue, 31 Mar, arriving in Chicago Midway.Price includes taxes and charges.From RM1,288, select.
Houston.RM1,341 per passenger.Departing Tue, 24 Mar, returning Wed, 25 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 24 Mar, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Wed, 25 Mar, arriving in Chicago Midway.Price includes taxes and charges.From RM1,341, select.
Houston.RM1,361 per passenger.Departing Sun, 13 Sep, returning Fri, 18 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 13 Sep, arriving in Houston Hobby.Inbound direct flight with Southwest Airlines departs from Houston Hobby on Fri, 18 Sep, arriving in Chicago Midway.Price includes taxes and charges.From RM1,361, select.
Houston.RM1,367 per passenger.Departing Sat, 12 Dec, returning Sat, 16 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 12 Dec, arriving in Houston Hobby.Inbound indirect flight with Delta, departs from Houston Hobby on Sat, 16 Jan, arriving in Chicago Midway.Price includes taxes and charges.From RM1,367, select.
Houston.RM1,387 per passenger.Departing Tue, 15 Dec, returning Sat, 19 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 15 Dec, arriving in Houston Hobby.Inbound indirect flight with Delta, departs from Houston Hobby on Sat, 19 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,387, select.
Houston.RM1,568 per passenger.Departing Thu, 15 Oct, returning Tue, 20 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 15 Oct, arriving in Houston Hobby.Inbound indirect flight with Delta, departs from Houston Hobby on Tue, 20 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM1,568, select.

Find the cheapest month to fly from Chicago to Houston Hobby

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Houston Hobby flights are currently cheapest in April.
Mar
from RM1,288
Apr
from RM762
May
from RM770
Jun
from RM1,046
Jul
from RM1,079
Aug
from RM1,040
Sep
from RM1,361
Oct
from RM1,568
Nov
from RM2,045
Dec
from RM1,387
Jan
Find prices
Feb
Find prices

Direct flights from Chicago to Houston Hobby

Chicago to Houston Hobby: Alternative routes

Compare routes from Chicago to Houston below. You may find an airport to fly into that's cheaper, faster, or easier than Houston Hobby.

Houston Hobby

16km from central Houston
Closest
from RM762
Search flights

Houston George Bush Intercntl.

25km from central Houston
Cheapest
from RM484
Search flights

Houston Ellington Field

28km from central Houston
Search flights

Galveston

74km from central Houston
Search flights

Chicago to Houston: Flight information

The things to know before you go.
Cheapest flight foundRM762
Cheapest month to flyApril
Average flight time2 hrs, 38 mins
Most popular airlineSouthwest Airlines
Average flights per week41

Check out these Houston hotels

Ready to plan your stay? Other travellers rate these Houston hotels for cleanliness, service and location.
Wanderstay Boutique Hotel
2.97 km from city centre
RM1,375
Per night
The Post Oak Hotel at Uptown Houston
8.54 km from city centre
RM4,705
Per night
La Maison in Midtown an Urban B&B
1.79 km from city centre
RM854
Per night
Wanderstay Boutique Hotel
2.97 km from city centre
RM1,375
Per night
The Post Oak Hotel at Uptown Houston
8.54 km from city centre
RM4,705
Per night
La Maison in Midtown an Urban B&B
1.79 km from city centre
RM854
Per night
Explore top-rated hotels

Finding cheap flights from Chicago to Houston Hobby: Frequently asked questions

The best price we found for a return flight from Chicago to Houston Hobby is RM762. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 38 minutes is the average flight time from Chicago to Houston Hobby.
Southwest Airlines flies direct from Chicago to Houston Hobby.
As of March 2026, there are 41 flights per week flying from Chicago to Houston Hobby.
The cheapest month to fly from Chicago to Houston Hobby is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Houston Hobby Airport on Saturday, 25 April 2026.
Yes – the average flight time is 2 hours and 38 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Houston Hobby but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Houston is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Houston Hobby is Southwest Airlines .

Travelling from Chicago to William P. Hobby Airport (HOU): What you need to know

  • Your adventure begins at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to William P. Hobby Airport (HOU) departing from either of these.

  • Houston (where William P. Hobby Airport is located) and Chicago share the UTC-5 timezone. With no time difference, coordinating plans between the cities is hassle-free.

  • Get to the airport on time so you don't miss your flight from Chicago to HOU. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.

  • In peak travel periods, allow for longer wait times and arrive earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international journeys.

Airports in Chicago

O'Hare International Airport (ORD)

  • Located around 40 kilometres from central Chicago, ORD can be reached in about 35 minutes by car, depending on traffic. The journey on public transport will take roughly 55 minutes.

  • Booked an early flight from Chicago to William P. Hobby Airport? Avoid the hassle of rushing to the terminal (and sneak in some bonus sleep) by staying at one of these hotels near O'Hare International Airport:

  • When it comes to the on-time performance of O'Hare International Airport, 74.85% of flights meet their scheduled arrival time.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Consider beginning your travels from Chicago Midway International Airport (MDW). You can book a direct Chicago to William P. Hobby Airport (HOU) plane ticket with departures from this hub.

  • From MDW, direct flights from Chicago to HOU are offered by Southwest Airlines.

  • Southwest Airlines has the largest share of bookings on the MDW to HOU route.

  • With 79.57% of services arriving as planned, Southwest Airlines is the top on-time carrier flying between Chicago Midway International Airport and William P. Hobby Airport.

  • MDW is about 19 kilometres from central Chicago. It'll take you 20 minutes or so to get to the airport by car from the city centre. Public transport takes approximately 45 minutes.

  • Want to enjoy an extra night away before your Chicago to HOU flight? Unwind in a hotel near Chicago Midway International Airport before your break officially begins. These stays have a room with your name on it:

  • When it comes to keeping flights punctual, Chicago Midway International Airport has an on-time arrival performance of 77.88%.

  • The street address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The trip to RFD from the centre of Chicago is around 4 hours 15 minutes on public transport. If you're planning to travel by car, it'll take you roughly 1 hour 25 minutes to cover the 137 kilometres or so.

  • Sleep a little longer and still make your Chicago to William P. Hobby Airport flight with time to spare. These hotels near Chicago Rockford International Airport make departure day a breeze if you're flying out first thing:

  • The on-time performance rating of RFD is 76.19%. In simpler terms, that's how often flights that depart this airport arrive as planned.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About William P. Hobby Airport (HOU)

Getting from William P. Hobby Airport (HOU) to central Houston

  • William P. Hobby Airport is about 16 kilometres from central Houston. The time it takes to get there by cab or car hire will depend on the time of day. Do a little research before you go.

  • Travelling by public transport takes about 1 hour 40 minutes.

How to find the cheapest flights from Chicago to William P. Hobby Airport (HOU)

  • Right now, RM381 is the best price we've found for a one-way ticket from Chicago to William P. Hobby Airport. The cheapest price for a return flight is RM762. Keep in mind fares can change due to demand at the time of booking.

  • Don't leave everything to the last minute. You're more likely to find cheap flights from Chicago to HOU if you book in advance. Airlines often offer some excellent early bird deals.

  • If you have some flexibility with your trip dates, use the 'Whole month' search tool. It'll give you the cheapest price across each month when searching for your Chicago to William P. Hobby Airport ticket.

  • Finding a cheap plane ticket from Chicago to HOU couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know as soon as there's a price drop.

  • Filters make it easier to land a deal on your flight from Chicago to William P. Hobby Airport. Pick the airlines, flight times and number of stops that match your plans. Then sort the results by 'Cheapest' to find the most affordable option fast.

The best time to fly from Chicago to William P. Hobby Airport (HOU)

  • April is the quietest month for flights from Chicago to William P. Hobby Airport (HOU), while July is the most popular. Pick the best time to visit Houston based on whether you want a laid-back vibe or a lively atmosphere.

  • Before locking in your Chicago to HOU plane ticket, consider the weather you're most comfortable in. August is the warmest month in Houston, with temperatures ranging from 24ºC (75ºF) to 40ºC (104ºF).

  • Search for cheap tickets from Chicago to William P. Hobby Airport in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between 5ºC (41ºF) and 19ºC (66ºF).

More about Houston

Explore more of the United States

  • You've seen Houston, now it's time to discover more of the United States. Travel around 241 kilometres west to Austin to tick off its top sights. From Texas State Capitol to Central Park and Austin Museum of Art, Downtown, your itinerary will be busy.

  • Around 290 kilometres south-west of Houston, Corpus Christi is another essential stop in the United States. No visit is complete without checking out Texas State Aquarium, Bayfront Park and Corpus Christi Cathedral.

Plan the rest of your trip from Chicago to Houston

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.