Flights from Chicago

Flights tailored to your budget

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Cheap flight offers from Chicago

Find cheap flight tickets and last-minute flight deals from Chicago

Southwest Airlines
Mon, 12-14 (CHI) Chicago -> (NYC) New York City
Direct
Southwest Airlines
Wed, 12-16 (NYC) New York City -> (CHI) Chicago
Direct

Price found 5 days ago
from Can$371
Southwest Airlines
Mon, 01-25 (CHI) Chicago -> (NYC) New York City
Direct
Southwest Airlines
Wed, 01-27 (NYC) New York City -> (CHI) Chicago
Direct

Price found 5 days ago
from Can$371
United
Tue, 04-27 (CHI) Chicago -> (YYC) Calgary
Direct
United
Fri, 04-30 (YYC) Calgary -> (CHI) Chicago
Direct

Price found 8 days ago
from Can$390
Southwest Airlines
Thu, 12-24 (CHI) Chicago -> (NYC) New York City
Direct
Southwest Airlines
Sat, 12-26 (NYC) New York City -> (CHI) Chicago
Direct

Price found 5 days ago
from Can$390
Air Canada
Fri, 12-25 (CHI) Chicago -> (YTO) Toronto
Direct
Air Canada
Thu, 01-07 (YTO) Toronto -> (CHI) Chicago
Direct

Price found 4 days ago
from Can$422
Air Canada
Sun, 01-10 (CHI) Chicago -> (YVR) Vancouver
Direct
Air Canada
Tue, 01-19 (YVR) Vancouver -> (CHI) Chicago
Direct

Price found 12 days ago
from Can$770
Air Canada
Mon, 06-21 (CHI) Chicago -> (REK) Reykjavík
Direct
Air Canada
Mon, 08-16 (REK) Reykjavík -> (CHI) Chicago
Direct

Price found Yesterday
from Can$805
SAS
Tue, 11-10 (CHI) Chicago -> (FRA) Frankfurt
Direct
SAS
Tue, 11-17 (FRA) Frankfurt -> (CHI) Chicago
Direct

Price found Yesterday
from Can$1,143
DELTA
Fri, 11-20 (CHI) Chicago -> (LAS) Las Vegas
Direct

Price found Yesterday
from Can$229
United
Thu, 12-24 (CHI) Chicago -> (IAD) Washington
Direct

Price found 2 days ago
from Can$242
Frontier Airlines
Tue, 11-17 (CHI) Chicago -> (PBG) Plattsburgh

Price found 15 days ago
from Can$279
United
Tue, 11-10 (CHI) Chicago -> (YYZ) Toronto
Direct

Price found 2 days ago
from Can$284
Porter Airlines
Mon, 11-09 (CHI) Chicago -> (YYZ) Toronto
Direct

Price found 2 days ago
from Can$290
DELTA
Thu, 11-12 (CHI) Chicago -> (BUF) Greater Buffalo
Direct

Price found 12 days ago
from Can$295
Copa Airlines
Thu, 12-10 (CHI) Chicago -> (UIO) Quito

Price found 7 days ago
from Can$543
Copa Airlines
Wed, 12-16 (CHI) Chicago -> (UIO) Quito

Price found 2 days ago
from Can$995
Southwest Airlines
Mon, 12-14 (CHI) Chicago -> (NYC) New York City
Direct
Southwest Airlines
Wed, 12-16 (NYC) New York City -> (CHI) Chicago
Direct

Price found 5 days ago
from Can$371
Southwest Airlines
Mon, 01-25 (CHI) Chicago -> (NYC) New York City
Direct
Southwest Airlines
Wed, 01-27 (NYC) New York City -> (CHI) Chicago
Direct

Price found 5 days ago
from Can$371
United
Tue, 04-27 (CHI) Chicago -> (YYC) Calgary
Direct
United
Fri, 04-30 (YYC) Calgary -> (CHI) Chicago
Direct

Price found 8 days ago
from Can$390
Southwest Airlines
Thu, 12-24 (CHI) Chicago -> (NYC) New York City
Direct
Southwest Airlines
Sat, 12-26 (NYC) New York City -> (CHI) Chicago
Direct

Price found 5 days ago
from Can$390
Air Canada
Fri, 12-25 (CHI) Chicago -> (YTO) Toronto
Direct
Air Canada
Thu, 01-07 (YTO) Toronto -> (CHI) Chicago
Direct

Price found 4 days ago
from Can$422
Air Canada
Sun, 01-10 (CHI) Chicago -> (YVR) Vancouver
Direct
Air Canada
Tue, 01-19 (YVR) Vancouver -> (CHI) Chicago
Direct

Price found 12 days ago
from Can$770
Air Canada
Mon, 06-21 (CHI) Chicago -> (REK) Reykjavík
Direct
Air Canada
Mon, 08-16 (REK) Reykjavík -> (CHI) Chicago
Direct

Price found Yesterday
from Can$805
SAS
Tue, 11-10 (CHI) Chicago -> (FRA) Frankfurt
Direct
SAS
Tue, 11-17 (FRA) Frankfurt -> (CHI) Chicago
Direct

Price found Yesterday
from Can$1,143

Info about flights from Chicago

Some useful information about flights from Chicago to plan your next trip

Best price last 15 days Can$284
Average flight duration 2h 23m
Cheapest month April
Average number of flights per week 28
Most frequent airlines American Airlines, Air Canada, United
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

The best flight deals from Chicago

Find the cheapest flights from Chicago with the search engine of Jetcost. Book your flight ticket from Chicago in seconds: Jetcost compares for you thousands of offers from travel agencies and scheduled and low cost airlines. In just a few clicks you will have the best flight deals from Chicago.

Flight prices from Chicago

The price of flights from Chicago may be influenced by route, seasonality, weekends and any national holidays.

The cheapest flight found in the last 15 days from Chicago in Canada is available at Can$260.

The airports in Chicago

Chicago has 3 airports: Midway, O'Hare, Rockford. Choosing one of the other airports could be even more convenient: with Jetcost you can compare offers for all available airports in Chicago to see which one is the most convenient for your trip.

Flights from Chicago

Filter your flight search from Chicago as you like

Find the flight that best suits your needs more easily with Jetcost: change your search at any time with the available filters. Choose whether to see offers for flights from Chicago that do not include stopovers or compare only flights from one or more airlines. With Jetcost you have a wide choice of criteria to find the ideal flight at the best price! All in just a few clicks and in real time, without having to repeat the flight search.

Other popular destinations

If you are looking for a flight from United States, you might also be interested in other popular destinations (which might be even cheaper): the most searched cities in United States by our users are: Boston, Miami, New York City, Orlando, Washington.

Frequently Asked Questions

Frequently asked questions about flights from Chicago

How much does an airline ticket from Chicago cost?

The lowest price recorded in the last 15 days for a flight from Chicago to an airport in Canada is Can$260.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular departure cities in United States?

The most popular departure cities according to our users' searches are: Boston, Miami, New York City, Orlando, Washington.