$96+ 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 4/4. 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
17 Feb — 24 Feb1
1 adult
1 adult, Economy, 0 bags

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 18 January 2026.

Good round-trip deal

$939 or less

Good one-way deal

$91 or less
Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 18 January 2026.

Fri 30/118:57
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Sun 1/205:54
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 18/1$261
Fri 6/319:23
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Sun 8/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 18/1$278
Wed 11/307:30
ORD
-
MIA
Nonstop3h 17m
United Airlines
Wed 18/309:00
MIA
-
ORD
Nonstop3h 38m
United Airlines
Deal found 17/1$308
Sat 28/216:10
ORD
-
PHX
Nonstop4h 08m
United Airlines
Tue 3/318:31
PHX
-
ORD
Nonstop3h 28m
United Airlines
Deal found 16/1$308
Sat 7/214:15
ORD
-
PHX
Nonstop4h 05m
Southwest
Sat 21/211:40
PHX
-
ORD
Nonstop3h 35m
Southwest
Deal found 17/1$313
Wed 11/307:30
ORD
-
MIA
Nonstop3h 17m
United Airlines
Fri 13/309:00
MIA
-
ORD
Nonstop3h 38m
United Airlines
Deal found 18/1$318
Sat 7/314:08
ORD
-
PHX
Nonstop4h 11m
United Airlines
Sat 7/318:31
PHX
-
ORD
Nonstop3h 28m
United Airlines
Deal found 18/1$318
Wed 6/510:35
ORD
-
SJU
1 stop9h 26m
JetBlue
Wed 6/523:59
SJU
-
ORD
1 stop10h 49m
JetBlue
Deal found 17/1$321
Fri 1/506:00
ORD
-
SJU
1 stop9h 47m
JetBlue
Fri 1/523:59
SJU
-
ORD
1 stop10h 49m
JetBlue
Deal found 17/1$323
Sat 11/416:15
ORD
-
PHX
Nonstop4h 00m
Southwest
Sat 18/409:00
PHX
-
ORD
Nonstop3h 30m
Southwest
Deal found 16/1$327
Sat 28/212:59
ORD
-
SJU
1 stop9h 30m
JetBlue
Fri 6/313:44
SJU
-
ORD
1 stop11h 12m
JetBlue
Deal found 17/1$332
Sun 3/506:00
ORD
-
SJU
1 stop9h 47m
JetBlue
Tue 5/523:25
SJU
-
ORD
1 stop10h 26m
JetBlue
Deal found 17/1$334

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 18 January 2026. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Auckland

Route

Departure

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 11/3

07:30-11:47

Nonstop3h 17m

Miami

Fri 13/3

09:00-11:38

Nonstop3h 38m

$318

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/4

10:00-22:01

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Wed 15/4

23:59-07:41

1 stop8h 42m

$332

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 28/2

12:59-00:29

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Fri 13/3

03:26-11:25

1 stop8h 59m

$332

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 11/4

10:00-22:01

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Wed 15/4

23:59-07:41

1 stop8h 42m

$332

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 28/2

10:00-20:05

1 stop8h 05m

San Juan Luis Munoz Marin Intl

Tue 3/3

05:10-11:49

1 stop8h 39m

$332

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 7/3

12:59-23:44

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Wed 11/3

03:26-11:25

1 stop8h 59m

$334

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 4/3

15:07-23:42

1 stop9h 35m

Phoenix Sky Harbor Intl

Tue 10/3

15:27-23:59

1 stop6h 32m

$342

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 7/3

20:10-23:18

Nonstop4h 08m

Phoenix Sky Harbor Intl

Sat 14/3

17:31-22:59

Nonstop3h 28m

$342

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 17/2

19:55-23:03

Nonstop4h 08m

Phoenix Sky Harbor Intl

Thu 19/2

13:55-18:32

Nonstop3h 37m

$342

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 30/1

07:40-18:05

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Sat 7/2

09:25-19:31

1 stop12h 06m

$353

Flights are sorted by cheapest return flights first.

Deals found on 17/1

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Chicago (average of $1,218). Flying from Chicago in September will prove the most costly (average of $2,525). 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 (1,556 flights per day), Toronto (820 flights per day), and Los Angeles (540 flights per day).

Madrid Barajas
Madrid Barajas
From $935
Kastrup Copenhagen
Kastrup Copenhagen
From $662
San Francisco
San Francisco
From $1,573
Houston Hobby
Houston Hobby
From $65

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
Kastrup Copenhagen
Kastrup Copenhagen
From $662
Madrid Barajas
Madrid Barajas
From $935
San Francisco
San Francisco
From $1,573

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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 18 January 2026.

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

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

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently January; 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 $1,477 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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