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Cheap flights from Houston Hobby Airport to Chicago from ₹ 10,538

HOU — CHI
25 Nov — 2 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Hobby to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Hobby to Chicago

Tue 8/1207:20 -
Nonstop2h 30m
Tue 15/1208:00 -
2 stops6h 00m
Deal found 23/10₹ 18,037
Sat 14/1105:00 -
Nonstop2h 25m
Sat 14/1118:20 -
Nonstop2h 50m
Deal found 23/10₹ 19,841
Fri 4/1220:40 -
Nonstop2h 30m
Mon 7/1220:50 -
Nonstop2h 40m
Deal found 21/10₹ 20,031
Thu 12/1112:55 -
1 stop4h 05m
Tue 17/1120:50 -
Nonstop2h 40m
Deal found 21/10₹ 20,601
Mon 23/1122:40 -
Nonstop2h 30m
Tue 1/1220:50 -
Nonstop2h 40m
Deal found 25/10₹ 20,791
Sat 5/1208:50 -
1 stop4h 05m
Mon 7/1216:15 -
1 stop5h 50m
Deal found 21/10₹ 21,455

Find flight deals from Hobby to Chicago

Round-trip from

₹ 18,037

One-way from

₹ 10,538

Popular in

October

Cheapest in

January

Average price

₹ 29,904
Southwest
  • Southwest
  • 8/12-15/12
  • 2 total stops
  • 8h 30m total
  • Houston to Chicago
Search Deals
Southwest
  • Southwest
  • 12/11-31/12
  • 1 total stop
  • 4h 05m total
  • Houston to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (₹ 292,829 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (₹ 50,832 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Thu 19/11

11:05-15:30

1 stop4h 25m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 11,012

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Fri 4/12

11:30-17:15

2 stops5h 45m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 11,012

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Thu 12/11

06:00-18:04

2 stops12h 04m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 11,487

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Mon 7/12

14:30-19:55

1 stop5h 25m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 14,050

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Fri 25/12

13:20-19:05

1 stop5h 45m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 14,050

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Thu 26/11

05:50-12:30

2 stops6h 40m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 14,525

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Sat 21/11

20:25-00:45

1 stop4h 20m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 15,000

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Sun 6/12

12:55-17:00

1 stop4h 05m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 17,183
Fastest return journey

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Wed 25/11

11:00-14:45

1 stop3h 45m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 17,563

HoustonChicago

HOU Houston Hobby - MDW Chicago Midway

HOUMDW

Houston Hobby

Wed 23/12

14:15-20:10

2 stops5h 55m

Chicago Midway

Wed 31/12

00:00-00:00

Nonstop0h 00m

₹ 21,455

Flights are sorted by cheapest return flights first.

Deals found on 22/10

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from Hobby to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hobby with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight from Houston Hobby Airport to Chicago

What is the cheapest month to book a flight from Houston Hobby Airport to Chicago?

Currently, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of ₹ 17,183). Flying from Houston Hobby Airport to Chicago in June is currently the most expensive (average of ₹ 31,423). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HOU to CHI?

When flying from Houston Hobby Airport to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost for a return flight from Houston Hobby Airport to Chicago?

Airfare is typical for this route at the moment.
Houston Hobby Airport to Chicago flights typically cost between ₹ 17,610 and ₹ 34,366 in December.
The cheapest return price found within the last 5 days was ₹ 18,037 on Southwest (8 Dec–15 Dec).

How often are flights from Houston to Chicago delayed?

About 24% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 113 minutes.

What is the most punctual flight time for Houston to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Houston to Chicago flights?

Over the past year, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.

How far ahead should I book a flight from Houston Hobby Airport to Chicago?

To ensure you get the cheapest price possible for a flight from Houston Hobby Airport to Chicago, you should look to book at least 78 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Reviews of airlines servicing Chicago

See what other customers who have flown with Frontier from Houston Hobby Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Frontier
5.5
Fair
2,515 reviews
Check prices

Entertainment

4.2

Comfort

5.4

Boarding

5.8

Food

4.5

Overall

5.5

Crew

6.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sept 2026

IAH - FLL

I was traveling with a lap infant and got to TSA only to be turned around saying that something was wrong with my boarding pass. I went to an agent and said nothing was wrong, printed me a board pass and I had to rejoin the line. The when I get to the ticket counter I found out they changed my family seat even though I purchased it prior. I was told I got a refund so I’ll see
Frontier
5.5
Fair
2,515 reviews
Frontier
5.5
Fair
2,515 reviews
Check prices

Entertainment

4.2

Comfort

5.4

Boarding

5.8

Food

4.5

Overall

5.5

Crew

6.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sept 2026

IAH - FLL

I was traveling with a lap infant and got to TSA only to be turned around saying that something was wrong with my boarding pass. I went to an agent and said nothing was wrong, printed me a board pass and I had to rejoin the line. The when I get to the ticket counter I found out they changed my family seat even though I purchased it prior. I was told I got a refund so I’ll see

Related info for your journey

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

    Airlines like Southwest and Delta fly from Houston Hobby Airport to Chicago in about 4h 05m. The time it takes to get you to your destination can typically vary by up to 6h 34m. Airlines will cover a distance of 1510 km. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Hobby to Chicago that include hotel bookings?

    Yes. In addition to deals on Hobby to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Hobby to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hobby to Chicago.

  • Can I find deals for business class flights from Hobby to Chicago?

    Yes. Cheapflights offers flight deals from Hobby to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Houston Hobby Airport to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of ₹ 17,183). Flying from Houston Hobby Airport to Chicago in June is currently the most expensive (average of ₹ 31,423). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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