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$790+ 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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
24 Nov — 1 Dec1
1 adult
1 adult, Economy, 0 bags

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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 25 October 2025.

Mon 8/1208:00AKL - ORD
2 stops35h 13mMultiple Airlines
Mon 15/1206:50ORD - AKL
2 stops35h 45mMultiple Airlines
Deal found 24/10$1,612
Sun 7/1214:50AKL - ORD
2 stops28h 23mMultiple Airlines
Sun 14/1206:50ORD - AKL
2 stops35h 45mMultiple Airlines
Deal found 23/10$1,621
Mon 24/1113:20AKL - ORD
2 stops22h 48mAmerican Airlines
Mon 8/1208:50ORD - AKL
1 stop30h 05mAmerican Airlines
Deal found 24/10$1,626
Mon 8/1213:20AKL - ORD
1 stop20h 59mBritish Airways
Mon 15/1207:00ORD - AKL
1 stop31h 55mBritish Airways
Deal found 24/10$1,637
Tue 9/1214:00AKL - ORD
2 stops43h 55mAir Canada
Tue 16/1212:50ORD - AKL
2 stops51h 10mAir Canada
Deal found 25/10$1,978
Thu 13/1120:10AKL - ORD
1 stop21h 50mMultiple Airlines
Sun 8/205:20ORD - AKL
2 stops28h 40mMultiple Airlines
Deal found 23/10$2,040
Thu 13/1120:10AKL - ORD
1 stop21h 50mMultiple Airlines
Wed 18/207:45ORD - AKL
2 stops27h 20mMultiple Airlines
Deal found 23/10$2,047
Mon 10/1106:50AKL - ORD
2 stops26h 51mMultiple Airlines
Tue 10/215:40ORD - AKL
2 stops30h 40mMultiple Airlines
Deal found 23/10$2,068
Sun 9/1106:15AKL - ORD
2 stops27h 26mAir Canada
Wed 11/215:40ORD - AKL
1 stop24h 20mAir Canada
Deal found 23/10$2,072
Wed 12/1107:00AKL - ORD
2 stops26h 41mAir Canada
Wed 18/208:45ORD - AKL
2 stops31h 15mAir Canada
Deal found 24/10$2,075
Sun 9/1107:00AKL - ORD
2 stops26h 41mAir Canada
Sat 7/215:59ORD - AKL
2 stops24h 01mAir Canada
Deal found 23/10$2,079

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 25 October 2025.

Return from

$1,567

One-way from

$863

Popular in

April

Cheapest in

February

Average price

$1,880
Air Canada
  • Air Canada
  • 3/2-24/2
  • 4 total stops
  • 59h 01m total
  • Auckland to Chicago
Search Deals
Air Canada
  • Air Canada
  • 7/2
  • 2 total stops
  • 27h 26m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($82 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($37 potential savings vs. average return price).
Search Deals
Average for return flights in October 2025
Search Deals

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 25 October 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

Tue 3/2

06:15-16:42

2 stops29h 27m

Chicago O'Hare Intl

Tue 24/2

15:40-16:50

2 stops30h 10m

$1,569

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 3/2

13:20-15:37

1 stop21h 17m

Chicago O'Hare Intl

Tue 24/2

07:18-10:05

1 stop31h 47m

$1,628

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 10/3

19:55-06:19

1 stop28h 24m

Chicago O'Hare Intl

Wed 11/3

08:53-05:55

1 stop27h 02m

$1,974

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 5/2

23:30-23:37

2 stops43h 07m

Chicago O'Hare Intl

Thu 26/2

09:00-21:20

2 stops41h 20m

$1,997

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 12/11

07:35-15:55

2 stops27h 20m

Chicago O'Hare Intl

Tue 17/2

16:45-09:10

1 stop21h 25m

$2,099

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 9/12

15:50-16:02

1 stop19h 12m

Chicago O'Hare Intl

Tue 16/12

13:15-12:20

2 stops28h 05m

$2,105

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 10/3

13:20-17:31

1 stop22h 11m

Chicago O'Hare Intl

Wed 11/3

13:10-08:10

2 stops25h 00m

$2,105

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 1/2

07:00-14:41

2 stops26h 41m

$790

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 2/2

14:00-14:41

1 stop19h 41m

$863

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 2/2

14:50-19:16

3 stops47h 26m

$903

Flights are sorted by cheapest return flights first.

Deals found on 25/10

Showing 1-10 of 17 results
1
2

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 24 October 2025.

The best time to book flights to Chicago is 63 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 19 hours 59 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 16 December 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 Wednesday 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, Air New Zealand and United Airlines.

Qantas Airways
Qantas Airways
From $1,436
Air New Zealand
Air New Zealand
From $1,644
United Airlines
United Airlines
From $1,434
Air Canada
Air Canada
From $1,452

What are the cheapest airlines that fly to Chicago?

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

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 25 October 2025.
Read reviews from past customers who have flown Air New Zealand, Qantas Airways, andUnited Airlines to the United States. 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 New Zealand
8.0
Very Good
517 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.0

Food

7.4

Comfort

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.
Air New Zealand
8.0
Very Good
517 reviews
Air New Zealand
8.0
Very Good
517 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.0

Food

7.4

Comfort

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.
Qantas Airways
7.5
Good
922 reviews
Air New Zealand
8.0
Very Good
517 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.0

Food

7.4

Comfort

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.
United Airlines
7.4
Good
8,997 reviews
Air New Zealand
8.0
Very Good
517 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.0

Food

7.4

Comfort

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.
American Airlines
7.2
Good
11,031 reviews
Air New Zealand
8.0
Very Good
517 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.0

Food

7.4

Comfort

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.
Air Canada
7.1
Good
10,357 reviews
Air New Zealand
8.0
Very Good
517 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.0

Food

7.4

Comfort

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

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, United Airlines is rated the highest out of the airlines that fly to Chicago.

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

    Chicago O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost $320, while return flights cost around $151.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $183, however they can be found for as little as $151.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Auckland Intl offers the quickest one-way flight (19 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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