$185+ Cheap flights from Chicago

CHI — AKL
7 Oct — 14 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

ChicagoPhoenix

ORD Chicago O'Hare Intl - PHX Phoenix Sky Harbor Intl

ORDPHX

Chicago O'Hare Intl

Thu 10/12

14:20-21:25

1 stop8h 05m

Phoenix Sky Harbor Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$236

ChicagoSan Juan

ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl

ORDSJU

Chicago O'Hare Intl

Thu 31/12

17:58-06:15

1 stop10h 17m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$238

ChicagoSan Juan

ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl

ORDSJU

Chicago O'Hare Intl

Wed 3/3

09:25-21:26

1 stop10h 01m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$246

ChicagoSan Juan

ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl

ORDSJU

Chicago O'Hare Intl

Sun 10/1

10:30-21:24

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$246

ChicagoSan Juan

ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl

ORDSJU

Chicago O'Hare Intl

Tue 6/10

08:55-14:44

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$262

ChicagoSan Juan

ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl

ORDSJU

Chicago O'Hare Intl

Mon 5/10

08:55-14:44

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$262

ChicagoSan Juan

ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl

ORDSJU

Chicago O'Hare Intl

Tue 8/12

14:16-21:00

Nonstop4h 44m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$262

ChicagoPhoenix

ORD Chicago O'Hare Intl - PHX Phoenix Sky Harbor Intl

ORDPHX

Chicago O'Hare Intl

Fri 27/11

06:23-11:35

1 stop6h 12m

Phoenix Sky Harbor Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$274

ChicagoPhoenix

ORD Chicago O'Hare Intl - PHX Phoenix Sky Harbor Intl

ORDPHX

Chicago O'Hare Intl

Mon 15/2

16:05-18:55

Nonstop3h 50m

Phoenix Sky Harbor Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$275

ChicagoPhoenix

ORD Chicago O'Hare Intl - PHX Phoenix Sky Harbor Intl

ORDPHX

Chicago O'Hare Intl

Sun 6/12

06:00-15:44

1 stop10h 44m

Phoenix Sky Harbor Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$279

Flights are sorted by cheapest return flights first.

Deals found on 2/9

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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, February is the cheapest month in which you can book a flight from Chicago (average of $1,849). Flying from Chicago in August will prove the most costly (average of $3,116). 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 (1,082 flights per day), Detroit (962 flights per day), and Los Angeles (805 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $647
Madrid Barajas
Madrid Barajas
From $919
San Francisco
San Francisco
From $387

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 $64. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $64
Toronto
Toronto
From $189
San Francisco
San Francisco
From $387

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 February; 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 $1,480 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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