$181+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — AKL
11 Jul — 18 Jul1
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 11 June 2026. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Route

Departure

Return

Price

Cheapest return flight

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 14/9

07:30-11:54

Nonstop3h 24m

Miami

Wed 16/9

08:45-14:47

1 stop7h 02m

$413

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 24/8

08:48-13:50

1 stop7h 02m

Phoenix Sky Harbor Intl

Wed 26/8

23:05-07:56

1 stop6h 51m

$415

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 15/10

14:55-21:52

1 stop8h 57m

Phoenix Sky Harbor Intl

Mon 19/10

23:10-08:00

1 stop6h 50m

$415

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 18/9

19:37-21:29

Nonstop3h 52m

Phoenix Sky Harbor Intl

Mon 21/9

16:49-23:59

1 stop5h 10m

$423

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 29/6

20:02-05:29

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Thu 2/7

01:00-09:00

1 stop9h 00m

$442

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 26/9

15:00-23:44

1 stop7h 44m

Miami

Thu 1/10

16:01-18:32

Nonstop3h 31m

$452

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 2/12

17:55-00:52

1 stop5h 57m

Miami

Mon 7/12

07:00-12:06

1 stop6h 06m

$468

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/9

08:55-14:44

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Sat 19/9

16:55-23:40

1 stop7h 45m

$468

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 15/9

07:20-14:33

1 stop9h 13m

Phoenix Sky Harbor Intl

Sun 20/9

07:08-19:21

1 stop10h 13m

$475

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 24/9

07:20-14:33

1 stop9h 13m

Phoenix Sky Harbor Intl

Wed 7/10

10:12-18:53

1 stop6h 41m

$475

Flights are sorted by cheapest return flights first.

Deals found on 10/6

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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, May is the cheapest month in which you can book a flight from Chicago (average of $244). Flying from Chicago in September will prove the most costly (average of $2,211). 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: Detroit (1,298 flights per day), New York (1,260 flights per day), and Los Angeles (881 flights per day).

Los Angeles
Los Angeles
From $184
Kastrup Copenhagen
Kastrup Copenhagen
From $655
Madrid Barajas
Madrid Barajas
From $930

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 $65. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $65
Los Angeles
Los Angeles
From $184
Toronto
Toronto
From $191

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 74 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

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 11 June 2026.

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

    The most popular destinations from Chicago this month are Boston, Amman Queen Alia Intl Airport, Atlanta. The top year-round destinations include Boston, Atlanta, Ahmedabad.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently May; with September 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 $1,397 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!

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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