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$106+ 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 31/12. 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
21 Nov — 28 Nov1
1 adult
1 adult, Economy

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 22 October 2025.

Good one-way deal

$664 or less
Price to beat on a one-way flight from Chicago.
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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 22 October 2025.

Tue 25/1111:40ORD - MIA
Nonstop3h 07mSpirit Airlines
Sun 7/1216:08MIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 20/10$206
Mon 12/117:55ORD - MIA
Nonstop3h 20mUnited Airlines
Thu 15/117:35MIA - ORD
Nonstop3h 42mUnited Airlines
Deal found 21/10$211
Thu 29/112:45ORD - MIA
1 stop8h 09mUnited Airlines
Thu 5/212:18MIA - ORD
Nonstop3h 37mUnited Airlines
Deal found 21/10$222
Sat 1/1109:27ORD - MIA
Nonstop3h 03mSpirit Airlines
Sat 8/1107:20MIA - ORD
Nonstop3h 27mSpirit Airlines
Deal found 20/10$228
Sat 17/113:00ORD - MIA
1 stop8h 20mUnited Airlines
Tue 20/116:19MIA - ORD
Nonstop3h 36mUnited Airlines
Deal found 20/10$239
Mon 9/215:45ORD - MIA
1 stop5h 10mSouthwest
Wed 18/206:55MIA - ORD
1 stop5h 15mSouthwest
Deal found 20/10$258
Mon 15/1212:39ORD - MIA
Nonstop3h 15mUnited Airlines
Sun 21/1207:15MIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 20/10$263
Wed 19/1107:35ORD - MIA
Nonstop3h 14mUnited Airlines
Mon 24/1107:00MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 20/10$274
Thu 11/1212:50ORD - PHX
Nonstop3h 58mUnited Airlines
Mon 15/1213:45PHX - ORD
Nonstop3h 33mUnited Airlines
Deal found 20/10$281
Sat 13/1215:05ORD - PHX
1 stop9h 54mAlaska Airlines
Tue 16/1206:02PHX - ORD
1 stop16h 48mAlaska Airlines
Deal found 22/10$284
Tue 24/215:45ORD - MIA
1 stop5h 15mSouthwest
Tue 3/306:55MIA - ORD
1 stop5h 15mSouthwest
Deal found 20/10$286
Wed 17/1220:59ORD - PHX
1 stop23h 55mAlaska Airlines
Wed 24/1206:06PHX - ORD
1 stop23h 23mAlaska Airlines
Deal found 21/10$286

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 22 October 2025. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Auckland

Route

Departure

Return

Price

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 17/12

15:05-23:59

1 stop9h 54m

Phoenix Sky Harbor Intl

Wed 24/12

08:20-20:02

1 stop10h 42m

$284

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 24/1

08:00-19:25

2 stops12h 25m

Phoenix Sky Harbor Intl

Sat 31/1

16:00-23:37

1 stop6h 37m

$340

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/3

08:50-13:13

Nonstop3h 23m

Miami

Wed 4/3

14:15-16:59

Nonstop3h 44m

$351

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 24/1

07:30-17:42

1 stop11h 12m

Phoenix Sky Harbor Intl

Fri 30/1

00:59-08:47

1 stop6h 48m

$356

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 4/12

07:50-15:45

1 stop8h 55m

Phoenix Sky Harbor Intl

Thu 4/12

00:59-08:40

1 stop6h 41m

$368

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 14/11

07:35-11:49

Nonstop3h 14m

Miami

Tue 18/11

07:00-09:29

Nonstop3h 29m

$375

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 19/11

07:35-11:49

Nonstop3h 14m

Miami

Mon 24/11

17:20-23:34

1 stop7h 14m

$375

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 6/12

16:20-00:46

1 stop7h 26m

Miami

Thu 18/12

12:36-16:54

1 stop5h 18m

$378

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 17/11

13:04-20:46

1 stop6h 42m

Miami

Wed 19/11

08:05-12:19

1 stop5h 14m

$378

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/1

17:55-00:57

1 stop6h 02m

Miami

Sat 17/1

07:00-13:23

1 stop7h 23m

$378

Flights are sorted by cheapest return flights first.

Deals found on 20/10

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 $811). Flying from Chicago in August will prove the most costly (average of $2,084). 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 (1,398 flights per day), Detroit (994 flights per day), and Atlanta (632 flights per day).

Dallas/Fort Worth
Dallas/Fort Worth
From $1,433
Kastrup Copenhagen
Kastrup Copenhagen
From $664
San Francisco
San Francisco
From $1,579

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Kastrup Copenhagen, with prices starting at $664. Explore other affordable destinations below.

Kastrup Copenhagen
Kastrup Copenhagen
From $664
Dallas/Fort Worth
Dallas/Fort Worth
From $1,433
San Francisco
San Francisco
From $1,579

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 134,765 searches.
Read through reviews of airlines serving Chicago, such as Air Canada. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,344 reviews
Check prices

Food

6.3

Entertainment

6.8

Crew

7.8

Boarding

7.3

Overall

7.1

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Shawna,Sept 2025

DCA - YYZ

Business class cabin was *freezing*. Landing was so hard it injured my back - no apology or explanation given
Air Canada
7.1
Good
10,344 reviews
Air Canada
7.1
Good
10,344 reviews
Check prices

Food

6.3

Entertainment

6.8

Crew

7.8

Boarding

7.3

Overall

7.1

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Shawna,Sept 2025

DCA - YYZ

Business class cabin was *freezing*. Landing was so hard it injured my back - no apology or explanation given

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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 22 October 2025.

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

    The most popular destinations from Chicago this month are Boston, Atlanta, Ahmedabad. 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 August 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 $1,831 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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