Cheap flights from Hobby (HOU) to Chicago (CHI)

HOU — CHI
May 29 — Jun 51

The best prices from Houston Hobby to Chicago are usually found in August or July, booked 60 days in advance, depart on a Tuesday or Saturday and return on a Wednesday

How to find the cheapest flight from Hobby to Chicago

All the information you need to plan the best HOU to CHI flight in 2022: compare Hobby to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

HOU - CHI

Price

$79 - $169

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inDecemberHigh demand for flights, 23% potential price rise
Cheapest inAugustBest time to find cheap flights, 39% potential price drop
Average price$117Average for round-trip flights in May 2022
Round-trip from$79From Houston Hobby to Chicago (CHI)

What is the cheapest day to fly round-trip from Houston Hobby Airport to Chicago?

Thursday flights are found to be more expensive to fly from Houston Hobby Airport to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

To save on the cost of your flight from Houston Hobby Airport to Chicago, book at least 61 days before your planned departure. Booking around this time can save you about 15% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $135 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $154.

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

Flights from Houston Hobby Airport to Chicago lean towards being more expensive in December. Prices are generally better when you fly from Houston Hobby Airport to Chicago in August, with the cheapest ticket starting at $48.

When is the cheapest time to fly from Houston Hobby Airport to Chicago (HOU - CHI)?

A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight at noon.

Cheap flights from Hobby to Chicago in May, June 2022

The best prices found for HOU to CHI flights for May, June
Jun 3 - Jun 17
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

4h 42m
MDW

Chicago Midway

HOU

Houston Hobby

1 stop

6h 48m
$341

Allegiant Air

View Deal

Deal found 5/21/22

Jun 4 - Jun 6
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

4h 36m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

6h 53m
$397

American Airlines

View Deal

Deal found 5/22/22

Jun 24 - Jul 4
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

5h 55m
MDW

Chicago Midway

HOU

Houston Hobby

1 stop

5h 19m
$415

Allegiant Air

View Deal

Deal found 5/21/22

Hobby to Chicago 2022 flight deals

Cheap flights to Chicago from Hobby found for this year
Aug 12 - Aug 15
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

5h 51m
MDW

Chicago Midway

HOU

Houston Hobby

1 stop

5h 30m
$234

Allegiant Air

View Deal

Deal found 5/23/22

Oct 18 - Oct 24
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

5h 13m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

5h 23m
$236

Delta

View Deal

Deal found 5/23/22

Aug 5 - Aug 8
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

5h 51m
MDW

Chicago Midway

HOU

Houston Hobby

1 stop

5h 30m
$260

Allegiant Air

View Deal

Deal found 5/24/22

Cheap Delta flights from Hobby to Chicago

Oct 18 - Oct 24
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

5h 13m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

5h 23m
$236

Delta

View Deal

Deal found 5/23/22

Sep 17 - Sep 21
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

5h 42m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

5h 23m
$290

Delta

View Deal

Deal found 5/23/22

Sep 14 - Sep 21
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

7h 27m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

2 stops

8h 10m
$294

Delta

View Deal

Deal found 5/23/22

Cheap American Airlines flights from Hobby to Chicago

Oct 19 - Oct 23
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

4h 00m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

4h 35m
$340

American Airlines

View Deal

Deal found 5/21/22

Aug 17 - Aug 23
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

5h 26m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

4h 51m
$350

American Airlines

View Deal

Deal found 5/23/22

Aug 27 - Sep 3
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

4h 49m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

6h 39m
$372

American Airlines

View Deal

Deal found 5/22/22

Last minute flights from Hobby to Chicago

Late deals on return flights to Chicago from Hobby, departing today and this week
Jun 3 - Jun 17
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

4h 42m
MDW

Chicago Midway

HOU

Houston Hobby

1 stop

6h 48m
$341

Allegiant Air

View Deal

Deal found 5/21/22

Jun 1 - Jun 4
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

5h 17m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

4h 53m
$430

American Airlines

View Deal

Deal found 5/22/22

May 29 - May 30
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

6h 59m
ORD

Chicago O'Hare Intl

HOU

Houston Hobby

1 stop

4h 48m
$467

American Airlines

View Deal

Deal found 5/23/22

One-way flights to Chicago All airports from Hobby

The cheapest one-way flights from Hobby to Chicago
Aug 19
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

5h 23m
$119

Allegiant Air

View Deal

Deal found 5/22/22

Aug 19
HOU

Houston Hobby

MDW

Chicago Midway

1 stop

5h 23m
$120

Allegiant Air

View Deal

Deal found 5/22/22

Sep 22
HOU

Houston Hobby

ORD

Chicago O'Hare Intl

1 stop

7h 27m
$126

Delta

View Deal

Deal found 5/23/22

Related info for your journey

Useful info, stats and facts about Hobby to Chicago flights.

Which airlines flying from Houston Hobby to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, Spirit Airlines, and American Airlines flying from Houston Hobby to Chicago have implemented new flexible cancellation policies.

Can I find flights from Houston Hobby Airport to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Houston Hobby Airport to Chicago for under $300. The cheapest flight booked recently is on Allegiant Air for just $234, but on average you can expect to pay $303.

Are there last-minute flights available from Houston Hobby Airport to Chicago for under $400?

There are currently 20+ open flights from Houston Hobby Airport to Chicago within the next 7 days for less than $400.

What are the cheapest airlines flying from Houston Hobby Airport to Chicago round-trip?

Our cheapest airline available from Houston Hobby Airport to Chicago is Allegiant Air. Our recent data shows that you can find tickets from as low as $234 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $236 and $340 round-trip.

What are the cheapest airlines to fly from Houston Hobby Airport to Chicago one-way?

One-way options have recently been found by users for as low as $119 on Allegiant Air. Other airlines that offer cheap prices include Delta from $126 and American Airlines from $148 one-way.

What are the most popular routes from Houston Hobby Airport to Chicago?

While some choose either Houston Hobby - Chicago Midway or Houston Hobby - Chicago Greater Rockford, Houston Hobby - Chicago O'Hare Intl is the most popular route from Houston Hobby Airport to Chicago.

What are the most popular airlines that fly from Houston Hobby Airport to Chicago?

Before booking your flight from Houston Hobby Airport to Chicago check out the most popular airlines for this route: Major Airline, American Airlines or Frontier.

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

On average you can expect to pay $260 for a flight from Houston Hobby Airport to Chicago. The cheapest flight overall is $92 while the most popular route, (Houston Hobby - Chicago O'Hare Intl) is currently priced at $130.

Alternative routes for Hobby to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Hobby to Chicago

The chart below displays the airlines Cheapflights users traveling from Hobby to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Spirit AirlinesCheapest$43Average$199FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
American AirlinesCheapest$78Average$197FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$78Average$202FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$199Average$509FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from Hobby to Chicago

See what time of day planes typically take off from Hobby to Chicago
10%of flight departuresEarly morningMidnight to 6 am
50%of flight departuresMorning6 am to noon
30%of flight departuresAfternoonNoon to 6 pm
10%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Hobby to Chicago

See how many times per day planes take to the skies headed from Hobby to Chicago
Sunday10daily flights
Monday10daily flights
Tuesday10daily flights
Wednesday10daily flights
Thursday10daily flights
Friday10daily flights
Saturday0daily flights