$211+ Cheap flights from Chicago

CHI — AKL
23 Oct — 30 Oct1
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

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Route

Departure

Return

Price

Cheapest return flight

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Tue 27/10

17:46-10:43

1 stop17h 57m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$211

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Tue 15/12

08:40-13:35

Nonstop4h 55m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$213

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Wed 21/10

08:40-11:28

Nonstop3h 48m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$213

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Tue 20/10

14:03-23:10

1 stop10h 07m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$230

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Sun 18/10

06:00-21:48

1 stop16h 48m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$230

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Fri 2/10

15:50-21:48

1 stop6h 58m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$230

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Sat 3/10

08:55-20:43

2 stops12h 48m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$239

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Sat 31/10

07:00-20:40

2 stops14h 40m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$239

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Sat 24/10

11:19-20:40

2 stops10h 21m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$239

ChicagoCalgary

ORD Chicago O'Hare Intl - YYC Calgary

ORDYYC

Chicago O'Hare Intl

Wed 18/11

12:38-01:17

2 stops12h 39m

Calgary

Wed 31/12

00:00-01:00

Nonstop0h 00m

$239

Flights are sorted by cheapest return flights first.

Deals found on 18/9

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago

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

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Chicago (average of $1,912). Flying from Chicago in August will prove the most costly (average of $3,200). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: New York (1,254 flights per day), Detroit (890 flights per day), and Los Angeles (626 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $665
Madrid Barajas
Madrid Barajas
From $944
San Francisco
San Francisco
From $397

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Houston Hobby, with prices starting at $66. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $66
Toronto
Toronto
From $194
San Francisco
San Francisco
From $397

When is the best time to book a flight from Chicago?

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 73 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.

Browse thousands of different options on Cheapflights for your next trip

Related info for your journey

  • What are the most popular destinations to fly to from Chicago?

    The most popular destinations from Chicago this month are Boston, Atlanta, Athens. The top year-round destinations include Atlanta, Boston, Mumbai.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently January; with August being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago?

    Here are some of the cheapest flight destinations from Chicago:
    Fly from Chicago to Auckland from $1,573 round trip

  • How does Cheapflights help users find flights from Chicago?

    900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    Cheapflights simply makes it quick and affordable to book flights from Chicago by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

  • Can Cheapflights find flights from Chicago with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

See more FAQs

Fly with Cheapflights

How does Cheapflights help users find flights from Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Chicago?

Cheapflights simply makes it quick and affordable to book flights from Chicago by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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Book with flexibility

Our users can plan ahead with confidence and find flights with no change fees

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