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$159+ 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 1/7. 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
2 May — 9 May1
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 27 April 2025.

Good round-trip deal

$506 or less

Good one-way deal

$280 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 27 April 2025.

Wed 4/609:55ORD - MIA
Nonstop3h 15mSpirit Airlines
Sat 7/615:15MIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 27/4$231
Tue 20/513:10ORD - PHX
Nonstop4h 03mUnited Airlines
Sat 24/523:20PHX - ORD
Nonstop3h 33mUnited Airlines
Deal found 27/4$362
Wed 11/611:00ORD - MIA
1 stop5h 10mDelta
Sat 14/605:30MIA - ORD
1 stop8h 00mDelta
Deal found 26/4$364
Tue 20/507:05ORD - PHX
1 stop7h 10mDelta
Tue 20/500:45PHX - ORD
1 stop5h 39mDelta
Deal found 27/4$397
Sat 31/507:00ORD - PHX
1 stop8h 05mAlaska Airlines
Tue 3/607:00PHX - ORD
1 stop14h 56mAlaska Airlines
Deal found 27/4$412
Wed 21/506:15ORD - PHX
1 stop7h 25mSouthwest
Wed 21/513:30PHX - ORD
1 stop8h 10mSouthwest
Deal found 27/4$432
Fri 27/618:17ORD - PHX
1 stop6h 27mSun Country Air
Sun 29/616:26PHX - ORD
1 stop22h 49mSun Country Air
Deal found 27/4$461
Tue 3/607:00ORD - MIA
Nonstop3h 17mUnited Airlines
Tue 3/616:16MIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 27/4$464
Tue 20/507:30ORD - MIA
2 stops8h 55mSouthwest
Wed 21/507:15MIA - ORD
1 stop5h 35mSouthwest
Deal found 27/4$478
Wed 4/607:37ORD - MIA
2 stops28h 39mMultiple Airlines
Sat 7/622:00MIA - ORD
2 stops20h 41mMultiple Airlines
Deal found 27/4$513
Tue 27/519:51ORD - MIA
1 stop20h 30mAlaska Airlines
Fri 30/518:21MIA - ORD
2 stops19h 47mAlaska Airlines
Deal found 27/4$687
Wed 14/516:03ORD - MIA
1 stop7h 10mJetBlue
Sun 18/511:11MIA - ORD
1 stop8h 25mJetBlue
Deal found 27/4$759

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 27 April 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 4/6

05:51-13:06

1 stop6h 15m

Miami

Sat 7/6

14:29-20:07

1 stop6h 38m

$275

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 20/5

13:10-15:13

Nonstop4h 03m

Phoenix Sky Harbor Intl

Sat 24/5

23:20-04:53

Nonstop3h 33m

$362

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 11/6

11:00-17:10

1 stop5h 10m

Miami

Sat 14/6

05:30-12:30

1 stop8h 00m

$364

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 20/5

07:05-12:15

1 stop7h 10m

Phoenix Sky Harbor Intl

Tue 20/5

00:45-08:24

1 stop5h 39m

$397

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 31/5

07:00-13:05

1 stop8h 05m

Phoenix Sky Harbor Intl

Tue 3/6

07:00-23:56

1 stop14h 56m

$412

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 21/5

06:15-11:40

1 stop7h 25m

Phoenix Sky Harbor Intl

Wed 21/5

13:30-23:40

1 stop8h 10m

$432

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 27/6

18:17-22:44

1 stop6h 27m

Phoenix Sky Harbor Intl

Sun 29/6

16:26-17:15

1 stop22h 49m

$461

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/6

07:00-11:17

Nonstop3h 17m

Miami

Tue 3/6

16:16-18:50

Nonstop3h 34m

$464

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 20/5

07:30-17:25

2 stops8h 55m

Miami

Wed 21/5

07:15-11:50

1 stop5h 35m

$478

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 4/6

07:37-13:16

2 stops28h 39m

Miami

Sat 7/6

22:00-17:41

2 stops20h 41m

$513

Flights are sorted by cheapest return flights first.

Deals found on 27/4

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, August is the cheapest month in which you can book a flight from Chicago (average of $365). Flying from Chicago in September will prove the most costly (average of $2,065). 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 (1,717 flights per day), Detroit (1,278 flights per day), and Los Angeles (719 flights per day).

Los Angeles

Los Angeles

From $1,661

Miami

Miami

From $182

Toronto

Toronto

From $302

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

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 $220. Explore other affordable destinations below.

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

Miami

Miami

From $182

Philadelphia

Philadelphia

From $188

Minneapolis St Paul

Minneapolis St Paul

From $293

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.
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Food

7.8

Comfort

8.1

Entertainment

7.3

Overall

8.8

Boarding

8.7

Crew

9.1

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
8.8
Very Good
62 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Food

7.8

Comfort

8.1

Entertainment

7.3

Overall

8.8

Boarding

8.7

Crew

9.1

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.
EVA Air
8.4
Very Good
1,182 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Food

7.8

Comfort

8.1

Entertainment

7.3

Overall

8.8

Boarding

8.7

Crew

9.1

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
8.1
Very Good
190 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Food

7.8

Comfort

8.1

Entertainment

7.3

Overall

8.8

Boarding

8.7

Crew

9.1

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
7,927 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Food

7.8

Comfort

8.1

Entertainment

7.3

Overall

8.8

Boarding

8.7

Crew

9.1

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
471 reviews
Air Tahiti Nui
8.8
Very Good
62 reviews
Check prices

Food

7.8

Comfort

8.1

Entertainment

7.3

Overall

8.8

Boarding

8.7

Crew

9.1

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 27 April 2025.

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

    The most popular destinations from Chicago this month are Atlanta, Boston, Barcelona-El Prat Airport. 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 August; 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!

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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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