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$117+ 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 17/12. 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
5 Sep — 12 Sep1
1 adult

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 31 August 2025.

Good round-trip deal

$511 or less

Good one-way deal

$283 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

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 31 August 2025.

Wed 5/1107:35ORD - MIA
Nonstop3h 14mUnited Airlines
Wed 12/1112:23MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 28/8$232
Sat 27/910:54ORD - MIA
Nonstop3h 17mUnited Airlines
Sat 4/1012:27MIA - ORD
Nonstop3h 28mUnited Airlines
Deal found 29/8$283
Tue 9/910:27ORD - MIA
Nonstop3h 12mSpirit Airlines
Wed 10/907:00MIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 30/8$285
Thu 25/907:30ORD - MIA
Nonstop3h 17mUnited Airlines
Sat 27/916:17MIA - ORD
Nonstop3h 30mUnited Airlines
Deal found 30/8$300
Tue 9/910:27ORD - MIA
Nonstop3h 12mSpirit Airlines
Thu 11/907:00MIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 30/8$319
Wed 24/919:50ORD - PHX
Nonstop3h 57mUnited Airlines
Sat 27/912:35PHX - ORD
Nonstop3h 37mUnited Airlines
Deal found 28/8$334
Thu 1/121:15ORD - PHX
Nonstop4h 02mUnited Airlines
Sun 11/113:57PHX - ORD
Nonstop3h 34mUnited Airlines
Deal found 29/8$336
Wed 19/1119:39ORD - PHX
Nonstop4h 02mUnited Airlines
Sun 23/1119:03PHX - ORD
Nonstop3h 27mUnited Airlines
Deal found 29/8$351
Thu 27/1107:35ORD - MIA
Nonstop3h 14mUnited Airlines
Tue 2/1212:23MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 28/8$353
Sun 28/920:03ORD - PHX
Nonstop3h 57mUnited Airlines
Sun 5/1007:00PHX - ORD
Nonstop3h 39mUnited Airlines
Deal found 29/8$361
Wed 24/919:50ORD - PHX
Nonstop3h 57mUnited Airlines
Sun 28/918:30PHX - ORD
Nonstop3h 29mUnited Airlines
Deal found 29/8$364
Tue 14/1015:50ORD - PHX
1 stop8h 49mAlaska Airlines
Sat 18/1006:00PHX - ORD
1 stop6h 50mAlaska Airlines
Deal found 29/8$366

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 31 August 2025. 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 5/11

07:35-11:49

Nonstop3h 14m

Miami

Wed 12/11

12:23-14:52

Nonstop3h 29m

$232

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 27/9

10:54-15:11

Nonstop3h 17m

Miami

Sat 4/10

12:27-14:55

Nonstop3h 28m

$283

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 9/9

10:27-14:39

Nonstop3h 12m

Miami

Thu 11/9

07:00-09:18

Nonstop3h 18m

$319

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 19/11

15:55-18:53

Nonstop3h 58m

Phoenix Sky Harbor Intl

Fri 21/11

13:55-18:28

Nonstop3h 33m

$351

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 19/11

14:40-19:49

1 stop6h 09m

Phoenix Sky Harbor Intl

Sat 22/11

15:30-19:59

Nonstop3h 29m

$351

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 22/10

18:28-21:57

1 stop5h 29m

Phoenix Sky Harbor Intl

Sat 25/10

07:00-12:39

Nonstop3h 39m

$351

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 27/11

07:35-11:49

Nonstop3h 14m

Miami

Tue 2/12

12:23-14:52

Nonstop3h 29m

$353

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sun 28/9

20:03-22:00

Nonstop3h 57m

Phoenix Sky Harbor Intl

Mon 29/9

07:00-12:39

Nonstop3h 39m

$361

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 4/10

11:10-12:59

Nonstop3h 49m

Phoenix Sky Harbor Intl

Tue 14/10

18:30-23:59

Nonstop3h 29m

$361

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 2/10

12:50-14:39

Nonstop3h 49m

Phoenix Sky Harbor Intl

Sat 4/10

10:50-16:29

Nonstop3h 39m

$361

Flights are sorted by cheapest return flights first.

Deals found on 29/8

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 $788). Flying from Chicago in September will prove the most costly (average of $2,044). 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 (1,328 flights per day), Detroit (930 flights per day), and Los Angeles (588 flights per day).

Miami
Miami
From $182
Toronto
Toronto
From $302
Mexico City Benito Juarez
Mexico City Benito Juarez
From $131
San Francisco
San Francisco
From $906

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Mexico City Benito Juarez, with prices starting at $223. Explore other affordable destinations below.

Mexico City Benito Juarez
Mexico City Benito Juarez
From $131
Miami
Miami
From $182
Philadelphia
Philadelphia
From $188
Toronto
Toronto
From $302

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
10,000 reviews
Check prices

Food

6.3

Boarding

7.3

Overall

7.1

Crew

7.8

Comfort

7.0

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

TPA - YYZ

The pre boarding was a bit confusing but we got through it.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Food

6.3

Boarding

7.3

Overall

7.1

Crew

7.8

Comfort

7.0

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

TPA - YYZ

The pre boarding was a bit confusing but we got through it.

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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 31 August 2025.

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

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

  • 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.

  • 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 $1,763 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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