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$784+ Cheap flights to 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 19/5. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
26 Mar — 2 Apr1
1 adult

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 134,765 searches and data was last updated on 21 March 2025.

Return from

$1,542

One-way from

$784

Popular in

April

Cheapest in

February

Average price

$2,006
American Airlines
  • American Airlines
  • 29/5-9/6
  • 4 total stops
  • 55h 44m total
  • Auckland to Chicago
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Air Canada
  • Air Canada
  • 19/5
  • 2 total stops
  • 25h 08m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($142 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease ($71 potential savings vs. average return price).
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Average for return flights in March 2025
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Find flight deals to Chicago

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 21 March 2025.

Thu 29/515:50AKL - ORD
2 stops31h 16mAmerican Airlines
Mon 9/616:57ORD - AKL
2 stops24h 28mAmerican Airlines
Deal found 19/3$1,542
Thu 29/506:00AKL - ORD
2 stops25h 43mMultiple Airlines
Mon 9/615:35ORD - AKL
2 stops32h 15mMultiple Airlines
Deal found 20/3$1,615
Sun 18/506:35AKL - ORD
2 stops46h 57mAir Canada
Sun 25/515:35ORD - AKL
2 stops30h 20mAir Canada
Deal found 20/3$1,844
Mon 28/720:15AKL - ORD
1 stop25h 46mAir New Zealand
Mon 4/822:00ORD - AKL
1 stop38h 30mAir New Zealand
Deal found 19/3$1,943
Sat 3/513:00AKL - ORD
2 stops25h 31mDelta
Sat 10/507:10ORD - AKL
2 stops30h 40mDelta
Deal found 19/3$1,985
Mon 8/913:50AKL - ORD
1 stop23h 13mUnited Airlines
Mon 22/914:00ORD - AKL
2 stops23h 00mUnited Airlines
Deal found 20/3$1,999
Wed 30/413:25AKL - ORD
2 stops27h 34mQantas Airways
Tue 20/519:13ORD - AKL
2 stops25h 52mQantas Airways
Deal found 19/3$2,091
Tue 1/709:40AKL - ORD
1 stop28h 30mEVA Air
Sun 20/700:30ORD - AKL
1 stop39h 45mEVA Air
Deal found 19/3$2,485
Thu 17/413:15AKL - ORD
1 stop42h 50mQatar Airways
Thu 24/419:20ORD - AKL
1 stop38h 25mQatar Airways
Deal found 19/3$3,626
Tue 1/710:00AKL - ORD
3 stops54h 25mSingapore Airlines
Tue 29/711:35ORD - AKL
3 stops51h 50mSingapore Airlines
Deal found 19/3$5,483
Mon 4/821:25AKL - ORD
2 stops49h 45mChina Southern
Thu 14/816:45ORD - AKL
3 stops53h 50mChina Southern
Deal found 20/3$10,948

Cheapflights Fare Finder

Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 134,765 searches and data was last updated on 21 March 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Auckland

Route

Departure

Return

Price

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

15:50-06:06

2 stops31h 16m

Chicago O'Hare Intl

Mon 9/6

16:57-10:25

2 stops24h 28m

$1,542

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

06:00-14:43

2 stops25h 43m

Chicago O'Hare Intl

Mon 9/6

15:35-16:50

2 stops32h 15m

$1,615

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 18/5

06:35-12:32

2 stops46h 57m

Chicago O'Hare Intl

Sun 25/5

15:35-14:55

2 stops30h 20m

$1,844

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 28/7

20:15-05:01

1 stop25h 46m

Chicago O'Hare Intl

Mon 4/8

22:00-05:30

1 stop38h 30m

$1,943

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 3/5

13:00-21:31

2 stops25h 31m

Chicago O'Hare Intl

Sat 10/5

07:10-06:50

2 stops30h 40m

$1,985

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 8/9

13:50-21:32

2 stops24h 42m

Chicago O'Hare Intl

Mon 22/9

14:00-06:00

2 stops23h 00m

$1,999

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 30/4

13:25-23:59

2 stops27h 34m

Chicago O'Hare Intl

Tue 20/5

19:13-14:05

2 stops25h 52m

$2,091

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 1/7

09:40-21:10

1 stop28h 30m

Chicago O'Hare Intl

Sun 20/7

00:30-09:15

1 stop39h 45m

$2,485

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 17/4

13:15-15:05

1 stop42h 50m

Chicago O'Hare Intl

Thu 24/4

19:20-02:45

1 stop38h 25m

$3,626

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 1/7

10:00-23:25

3 stops54h 25m

Chicago O'Hare Intl

Tue 29/7

11:35-08:25

3 stops51h 50m

$5,483

Flights are sorted by cheapest return flights first.

Deals found on 18/3

Showing 1-10 of 21 results
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Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to 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.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight from Auckland to Chicago. Price data was last updated on 14 March 2025.

The best time to book flights to Chicago is 41 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

How long is the flight to Chicago?

On average, a flight from Auckland to Chicago takes 24 hours 50 minutes. Flights to Chicago from other popular cities in New Zealand will vary in length. Below are a few examples of popular routes and their flight times.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly return from Auckland to Chicago. Price data was last updated on 1 September 2024.

Users looking for the lowest fares to Chicago should consider flying on Saturday afternoons, when prices are typically cheapest. Budget-minded travellers will want to avoid Saturday evenings, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Auckland to Chicago are Qantas Airways, United Airlines and Air New Zealand.

Qantas Airways

Qantas Airways

From $894

United Airlines

United Airlines

From $929

Air New Zealand

Air New Zealand

From $1,106

Air Canada

Air Canada

From $890

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Air Canada, Qantas Airways and United Airlines.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 21 March 2025.
See what other customers who have flown with Air Tahiti Nui, EVA Air and Singapore Airlines to Chicago have to say. 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
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Crew

9.1

Overall

8.7

Entertainment

7.2

Boarding

8.7

Food

7.8

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
8.7
Very Good
61 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Crew

9.1

Overall

8.7

Entertainment

7.2

Boarding

8.7

Food

7.8

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
1,170 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Crew

9.1

Overall

8.7

Entertainment

7.2

Boarding

8.7

Food

7.8

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.
Singapore Airlines
8.1
Very Good
1,282 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Crew

9.1

Overall

8.7

Entertainment

7.2

Boarding

8.7

Food

7.8

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
7,895 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Crew

9.1

Overall

8.7

Entertainment

7.2

Boarding

8.7

Food

7.8

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
7.9
Good
452 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Crew

9.1

Overall

8.7

Entertainment

7.2

Boarding

8.7

Food

7.8

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.

FAQs about flying to Chicago

  • Can I find cheaper flights to Chicago if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Chicago?

    Based on reviews from Cheapflights users, Air Canada is rated the highest out of the airlines that fly to Chicago.

  • What is the cheapest airport to fly to in Chicago?

    Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost $169, while return flights cost around $173.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $108, however they can be found for as little as $100.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Christchurch offers the quickest one-way flight (22 hours 59 minutes).

  • Does Chicago O'Hare Intl have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl?

    Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).

See more FAQs

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Airports serving Chicago

Book a flight to or from one of these Chicago airports.
Flights to Midway
Flights to O'Hare Intl
Flights from Midway
Flights from O'Hare Intl

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When you search for this flight to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

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Can Cheapflights notify me if prices for flights to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alerts, which notifies users when flight prices change. Track prices for your flight to Chicago today and book when you’re ready!

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