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$146+ 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 17/8. 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
22 Jul — 29 Jul1
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 17 July 2025.

Good round-trip deal

$507 or less

Good one-way deal

$281 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 17 July 2025.

Mon 1/907:25ORD - MIA
Nonstop3h 17mUnited Airlines
Mon 8/912:27MIA - ORD
Nonstop3h 28mUnited Airlines
Deal found 16/7$230
Tue 5/821:10ORD - MIA
1 stop12h 39mSpirit Airlines
Wed 6/813:35MIA - ORD
Nonstop3h 36mSpirit Airlines
Deal found 17/7$235
Thu 4/914:55ORD - MIA
1 stop4h 50mSouthwest
Sun 7/908:05MIA - ORD
1 stop5h 40mSouthwest
Deal found 15/7$264
Thu 21/815:10ORD - PHX
Nonstop3h 45mSouthwest
Sat 30/808:35PHX - ORD
Nonstop3h 30mSouthwest
Deal found 17/7$318
Sat 30/820:25ORD - PHX
Nonstop3h 46mAmerican Airlines
Fri 5/900:25PHX - ORD
Nonstop3h 36mAmerican Airlines
Deal found 16/7$320
Sun 31/814:13ORD - PHX
Nonstop4h 06mFrontier
Sun 7/917:06PHX - ORD
Nonstop3h 34mFrontier
Deal found 17/7$323
Sun 31/806:00ORD - PHX
1 stop7h 06mUnited Airlines
Tue 2/907:04PHX - ORD
Nonstop3h 39mUnited Airlines
Deal found 15/7$328
Fri 29/813:15ORD - MIA
1 stop24h 15mMultiple Airlines
Fri 5/907:00MIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 15/7$331
Sat 16/815:30ORD - MIA
1 stop4h 58mDelta
Tue 19/810:28MIA - ORD
1 stop7h 00mDelta
Deal found 15/7$365
Sat 4/1010:00ORD - PHX
1 stop7h 17mHawaiian Airlines
Sat 11/1011:10PHX - ORD
1 stop10h 49mHawaiian Airlines
Deal found 15/7$367
Sun 3/818:23ORD - SJU
Nonstop4h 43mSpirit Airlines
Fri 8/815:50SJU - ORD
1 stop16h 14mSpirit Airlines
Deal found 15/7$367
Thu 9/1008:20ORD - PHX
1 stop8h 57mAlaska Airlines
Sun 12/1011:57PHX - ORD
1 stop10h 02mAlaska Airlines
Deal found 15/7$390

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 17 July 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

Tue 29/7

08:09-12:23

Nonstop3h 14m

Miami

Sun 10/8

13:35-16:11

Nonstop3h 36m

$358

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 15/8

15:10-16:55

Nonstop3h 45m

Phoenix Sky Harbor Intl

Sun 17/8

16:50-22:20

Nonstop3h 30m

$358

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 18/12

15:45-22:05

1 stop5h 20m

Miami

Tue 23/12

07:00-11:10

1 stop5h 10m

$360

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 8/8

07:30-09:20

Nonstop3h 50m

Phoenix Sky Harbor Intl

Tue 12/8

06:00-14:42

1 stop6h 42m

$362

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 16/8

15:30-21:28

1 stop4h 58m

Miami

Tue 19/8

10:28-16:28

1 stop7h 00m

$365

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 3/9

08:00-14:58

1 stop8h 58m

Phoenix Sky Harbor Intl

Thu 4/9

18:10-05:00

1 stop8h 50m

$365

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/8

18:23-00:06

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Fri 8/8

15:50-07:04

1 stop16h 14m

$367

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 17/10

19:59-09:44

1 stop15h 45m

Phoenix Sky Harbor Intl

Mon 20/10

11:57-23:59

1 stop10h 02m

$378

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 1/1

06:00-10:08

Nonstop3h 08m

Miami

Wed 7/1

17:20-23:42

1 stop7h 22m

$378

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 7/8

06:00-10:35

1 stop6h 35m

Phoenix Sky Harbor Intl

Mon 11/8

23:59-08:37

1 stop6h 38m

$399

Flights are sorted by cheapest return flights first.

Deals found on 15/7

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 $738). Flying from Chicago in September will prove the most costly (average of $2,028). 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: Detroit (1,250 flights per day), New York (1,086 flights per day), and Los Angeles (773 flights per day).

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

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 $221. 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 Tahiti Nui, Fiji Airways, andDelta. 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 Tahiti Nui
8.6
Very Good
65 reviews
Check prices

Crew

9.0

Boarding

8.7

Overall

8.6

Comfort

8.0

Food

7.7

Entertainment

7.2

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Air Tahiti Nui
8.6
Very Good
65 reviews
Air Tahiti Nui
8.6
Very Good
65 reviews
Check prices

Crew

9.0

Boarding

8.7

Overall

8.6

Comfort

8.0

Food

7.7

Entertainment

7.2

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Fiji Airways
8.0
Very Good
201 reviews
Air Tahiti Nui
8.6
Very Good
65 reviews
Check prices

Crew

9.0

Boarding

8.7

Overall

8.6

Comfort

8.0

Food

7.7

Entertainment

7.2

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Delta
8.0
Very Good
7,959 reviews
Air Tahiti Nui
8.6
Very Good
65 reviews
Check prices

Crew

9.0

Boarding

8.7

Overall

8.6

Comfort

8.0

Food

7.7

Entertainment

7.2

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Air New Zealand
8.0
Very Good
496 reviews
Air Tahiti Nui
8.6
Very Good
65 reviews
Check prices

Crew

9.0

Boarding

8.7

Overall

8.6

Comfort

8.0

Food

7.7

Entertainment

7.2

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
United Airlines
7.4
Good
8,864 reviews
Air Tahiti Nui
8.6
Very Good
65 reviews
Check prices

Crew

9.0

Boarding

8.7

Overall

8.6

Comfort

8.0

Food

7.7

Entertainment

7.2

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

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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 17 July 2025.

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

    The most popular destinations from Chicago this month are Athens, Boston, Amman. 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 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 $1,961 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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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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