$138+ 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 24/3. 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
15 Apr — 22 Apr1
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 16 March 2026.

Good round-trip deal

$951 or less

Good one-way deal

$90 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 16 March 2026.

Sat 4/416:51
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Wed 8/416:06
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 14/3$208
Tue 14/410:55
ORD
-
MIA
Nonstop3h 05m
Spirit Airlines
Tue 21/406:30
MIA
-
ORD
1 stop11h 41m
Spirit Airlines
Deal found 15/3$218
Sat 4/416:51
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Tue 7/407:20
MIA
-
ORD
Nonstop3h 30m
Spirit Airlines
Deal found 14/3$329
Fri 17/407:50
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Tue 21/406:30
MIA
-
ORD
1 stop11h 41m
Spirit Airlines
Deal found 15/3$356
Sat 18/412:55
ORD
-
PHX
Nonstop4h 03m
United Airlines
Sat 18/418:00
PHX
-
ORD
Nonstop3h 30m
United Airlines
Deal found 12/3$367
Wed 8/407:17
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Wed 15/412:57
SJU
-
ORD
1 stop12h 27m
Spirit Airlines
Deal found 15/3$370
Sat 18/408:50
ORD
-
MIA
Nonstop3h 18m
United Airlines
Sat 25/408:55
MIA
-
ORD
Nonstop3h 36m
United Airlines
Deal found 16/3$376
Sat 25/416:15
ORD
-
PHX
Nonstop4h 00m
Southwest
Sat 2/516:55
PHX
-
ORD
Nonstop3h 25m
Southwest
Deal found 12/3$376
Sun 12/706:30
ORD
-
MIA
Nonstop3h 00m
Spirit Airlines
Wed 15/718:54
MIA
-
ORD
Nonstop3h 10m
Spirit Airlines
Deal found 15/3$381
Thu 26/310:55
ORD
-
MIA
Nonstop3h 05m
Spirit Airlines
Sat 28/306:00
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 16/3$389
Tue 14/416:10
ORD
-
PHX
1 stop9h 17m
Alaska Airlines
Sat 18/407:00
PHX
-
ORD
1 stop10h 02m
Alaska Airlines
Deal found 12/3$391
Tue 14/409:10
ORD
-
PHX
Nonstop4h 10m
United Airlines
Sat 18/418:00
PHX
-
ORD
Nonstop3h 30m
United Airlines
Deal found 12/3$393

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

Fly to

Route

Departure

Return

Price

Cheapest return flight

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 14/4

09:10-11:20

Nonstop4h 10m

Phoenix Sky Harbor Intl

Sat 18/4

18:00-23:30

Nonstop3h 30m

$393

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sun 26/4

19:15-21:10

Nonstop3h 55m

Phoenix Sky Harbor Intl

Tue 28/4

18:30-23:55

Nonstop3h 25m

$433

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 30/4

15:45-21:00

1 stop7h 15m

Phoenix Sky Harbor Intl

Sat 2/5

09:15-23:25

2 stops12h 10m

$471

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 28/4

10:30-16:30

2 stops8h 00m

Phoenix Sky Harbor Intl

Wed 29/4

10:55-22:55

2 stops10h 00m

$472

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 18/4

14:05-21:10

2 stops9h 05m

Phoenix Sky Harbor Intl

Mon 20/4

23:55-09:45

1 stop7h 50m

$486

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sun 7/6

20:13-22:10

Nonstop3h 57m

Phoenix Sky Harbor Intl

Sat 13/6

17:49-23:31

Nonstop3h 42m

$495

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 6/4

16:15-20:55

1 stop6h 40m

Phoenix Sky Harbor Intl

Mon 6/4

22:00-12:50

2 stops12h 50m

$516

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 29/4

05:15-10:46

1 stop4h 31m

Miami

Mon 11/5

08:05-13:01

1 stop5h 56m

$550

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 18/5

14:40-23:35

1 stop10h 55m

Phoenix Sky Harbor Intl

Tue 26/5

11:35-22:55

2 stops9h 20m

$555

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/6

13:15-22:48

1 stop8h 33m

San Juan Luis Munoz Marin Intl

Tue 16/6

06:15-16:44

1 stop11h 29m

$564

Flights are sorted by cheapest return flights first.

Deals found on 16/3

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.

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

Use this chart to determine the optimal time to book a return flight from Chicago to Auckland. Price data was last updated on 13 March 2026.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 15 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.

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

Currently, November is the cheapest month in which you can book a flight from Chicago (average of $735). Flying from Chicago in September will prove the most costly (average of $2,490). 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 (1,684 flights per day), Detroit (1,060 flights per day), and Orlando (959 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $659
Madrid Barajas
Madrid Barajas
From $936
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 $659
Madrid Barajas
Madrid Barajas
From $936

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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 16 March 2026.

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

    The most popular destinations from Chicago this month are Atlanta, Boston, Austin. 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 November; with September being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • 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

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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