$83+ 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 17/2. 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
28 Feb — 7 Mar1
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 29 January 2026.

Good round-trip deal

$911 or less

Good one-way deal

$86 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 29 January 2026.

Sat 14/316:51
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Wed 18/316:05
MIA
-
ORD
Nonstop3h 30m
Spirit Airlines
Deal found 27/1$143
Thu 26/208:59
ORD
-
MIA
1 stop10h 52m
Spirit Airlines
Thu 5/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 27/1$166
Sun 8/209:23
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Sun 15/207:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 27/1$172
Mon 9/218:57
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Sun 15/207:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 27/1$199
Sun 1/319:23
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Thu 5/321:53
MIA
-
ORD
1 stop11h 01m
Spirit Airlines
Deal found 29/1$204
Wed 11/307:30
ORD
-
MIA
Nonstop3h 17m
United Airlines
Wed 11/314:21
MIA
-
ORD
Nonstop3h 44m
United Airlines
Deal found 28/1$252
Tue 17/209:18
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Sun 22/221:53
MIA
-
ORD
1 stop11h 01m
Spirit Airlines
Deal found 27/1$255
Sun 22/219:23
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Sun 1/321:53
MIA
-
ORD
1 stop11h 01m
Spirit Airlines
Deal found 27/1$257
Tue 3/310:35
ORD
-
MIA
Nonstop3h 23m
United Airlines
Wed 11/309:00
MIA
-
ORD
Nonstop3h 38m
United Airlines
Deal found 27/1$260
Fri 17/418:34
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Sun 19/420:35
MIA
-
ORD
1 stop13h 37m
Spirit Airlines
Deal found 28/1$262
Fri 8/518:34
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Sun 10/515:47
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 26/1$265
Sat 7/320:10
ORD
-
PHX
Nonstop4h 08m
United Airlines
Tue 10/307:26
PHX
-
ORD
Nonstop3h 28m
United Airlines
Deal found 28/1$293

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 29 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 4/3

10:35-14:58

Nonstop3h 23m

Miami

Fri 6/3

16:10-18:55

Nonstop3h 45m

$293

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 9/5

15:15-02:07

1 stop9h 52m

San Juan Luis Munoz Marin Intl

Fri 15/5

23:59-09:48

1 stop10h 49m

$318

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 9/3

12:41-23:29

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Mon 16/3

03:26-11:25

1 stop8h 59m

$318

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/5

15:15-00:07

1 stop7h 52m

San Juan Luis Munoz Marin Intl

Fri 15/5

23:59-09:48

1 stop10h 49m

$318

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 21/2

06:04-16:56

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sat 28/2

05:10-12:04

1 stop8h 54m

$356

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 9/4

10:00-22:01

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 17/4

23:59-07:41

1 stop8h 42m

$356

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 18/3

13:57-21:18

1 stop6h 21m

Miami

Wed 25/3

16:44-21:10

1 stop5h 26m

$360

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 24/2

15:07-23:42

1 stop9h 35m

Phoenix Sky Harbor Intl

Fri 27/2

16:12-23:59

1 stop6h 47m

$360

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 31/3

20:10-22:15

Nonstop4h 05m

Phoenix Sky Harbor Intl

Tue 7/4

18:00-23:30

Nonstop3h 30m

$360

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/3

18:08-22:24

Nonstop3h 16m

Miami

Mon 9/3

17:36-20:20

Nonstop3h 44m

$378

Flights are sorted by cheapest return flights first.

Deals found on 28/1

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 $1,162). Flying from Chicago in September will prove the most costly (average of $2,409). 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 (1,287 flights per day), Detroit (870 flights per day), and Toronto (822 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $631
Madrid Barajas
Madrid Barajas
From $896
San Francisco
San Francisco
From $1,501
Houston Hobby
Houston Hobby
From $62

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 $62. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $62
Kastrup Copenhagen
Kastrup Copenhagen
From $631
Madrid Barajas
Madrid Barajas
From $896
San Francisco
San Francisco
From $1,501

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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 29 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 $1,392 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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