$93+ 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 30/3. 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
17 Mar — 24 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 15 February 2026.

Good round-trip deal

$909 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 15 February 2026.

Sun 1/319:23
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Sun 8/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 15/2$166
Mon 23/318:08
ORD
-
MIA
Nonstop3h 16m
United Airlines
Thu 26/309:00
MIA
-
ORD
Nonstop3h 38m
United Airlines
Deal found 14/2$184
Fri 6/309:18
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Sun 8/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 15/2$199
Tue 21/410:45
ORD
-
MIA
Nonstop3h 20m
United Airlines
Sat 25/408:55
MIA
-
ORD
Nonstop3h 36m
United Airlines
Deal found 14/2$200
Tue 3/309:18
ORD
-
MIA
1 stop10h 33m
Spirit Airlines
Sun 8/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 15/2$228
Sun 8/319:23
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Sun 15/306:00
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 13/2$232
Fri 24/418:25
ORD
-
MIA
Nonstop3h 20m
United Airlines
Wed 29/412:24
MIA
-
ORD
Nonstop3h 39m
United Airlines
Deal found 15/2$255
Wed 13/510:35
ORD
-
MIA
Nonstop3h 22m
United Airlines
Wed 20/512:10
MIA
-
ORD
Nonstop3h 40m
United Airlines
Deal found 12/2$260
Sat 25/409:10
ORD
-
PHX
Nonstop4h 10m
United Airlines
Sat 2/515:30
PHX
-
ORD
1 stop5h 28m
United Airlines
Deal found 15/2$263
Sat 25/409:10
ORD
-
PHX
Nonstop4h 10m
United Airlines
Sun 26/423:59
PHX
-
ORD
Nonstop3h 30m
United Airlines
Deal found 15/2$265
Tue 24/308:52
ORD
-
MIA
Nonstop3h 23m
United Airlines
Tue 24/318:34
MIA
-
ORD
1 stop6h 10m
United Airlines
Deal found 14/2$270
Wed 29/410:45
ORD
-
MIA
Nonstop3h 20m
United Airlines
Sat 2/516:15
MIA
-
ORD
Nonstop3h 40m
United Airlines
Deal found 14/2$271

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 15 February 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

Mon 23/3

18:08-22:24

Nonstop3h 16m

Miami

Thu 26/3

09:00-11:38

Nonstop3h 38m

$184

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 12/3

16:51-20:57

Nonstop3h 06m

Miami

Sat 14/3

06:00-08:25

Nonstop3h 25m

$232

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 2/5

11:05-13:10

Nonstop4h 05m

Phoenix Sky Harbor Intl

Tue 5/5

12:43-18:21

Nonstop3h 38m

$265

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 11/5

10:35-14:57

Nonstop3h 22m

Miami

Wed 13/5

12:10-14:50

Nonstop3h 40m

$293

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 10/5

07:14-11:37

Nonstop3h 23m

Miami

Wed 13/5

12:10-14:50

Nonstop3h 40m

$316

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 14/4

07:20-09:22

Nonstop4h 02m

Phoenix Sky Harbor Intl

Sat 18/4

18:00-23:30

Nonstop3h 30m

$326

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 7/4

20:10-22:15

Nonstop4h 05m

Phoenix Sky Harbor Intl

Sat 11/4

16:34-00:29

1 stop5h 55m

$357

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/3

14:38-20:50

1 stop5h 12m

Miami

Wed 18/3

06:00-10:00

1 stop5h 00m

$359

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 17/4

19:20-21:15

Nonstop3h 55m

Phoenix Sky Harbor Intl

Tue 21/4

18:30-23:55

Nonstop3h 25m

$359

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 1/5

21:15-23:23

Nonstop4h 08m

Phoenix Sky Harbor Intl

Wed 13/5

23:30-05:01

Nonstop3h 31m

$359

Flights are sorted by cheapest return flights first.

Deals found on 15/2

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, November is the cheapest month in which you can book a flight from Chicago (average of $703). Flying from Chicago in September will prove the most costly (average of $2,396). 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 (1,167 flights per day), Detroit (834 flights per day), and Toronto (804 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $630
Madrid Barajas
Madrid Barajas
From $895
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 $630
Madrid Barajas
Madrid Barajas
From $895

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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 15 February 2026.

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

    The most popular destinations from Chicago this month are Atlanta, Ahmedabad, Boston. 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 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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