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$1,025+ 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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
11 May — 18 May1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

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 11 April 2026.

Mon 11/516:25
AKL
-
ORD
1 stop35h 33m
American Airlines
Tue 26/518:02
ORD
-
AKL
2 stops27h 03m
American Airlines
Deal found 8/4$1,671
Mon 25/516:25
AKL
-
ORD
1 stop36h 24m
American Airlines
Mon 1/618:59
ORD
-
AKL
2 stops26h 06m
American Airlines
Deal found 9/4$1,709
Mon 11/516:25
AKL
-
ORD
1 stop38h 54m
American Airlines
Fri 22/517:10
ORD
-
AKL
2 stops27h 10m
American Airlines
Deal found 9/4$1,740
Tue 12/506:00
AKL
-
ORD
2 stops34h 59m
Qantas Airways
Fri 22/516:29
ORD
-
AKL
1 stop43h 26m
Qantas Airways
Deal found 10/4$1,748
Mon 11/516:25
AKL
-
ORD
1 stop33h 06m
American Airlines
Mon 25/518:59
ORD
-
AKL
2 stops26h 06m
American Airlines
Deal found 11/4$1,885
Fri 1/514:00
AKL
-
ORD
2 stops32h 50m
Multiple Airlines
Fri 15/508:30
ORD
-
AKL
3 stops35h 15m
Multiple Airlines
Deal found 6/4$1,892
Sun 16/816:25
AKL
-
ORD
1 stop33h 45m
American Airlines
Sun 23/818:03
ORD
-
AKL
2 stops27h 07m
American Airlines
Deal found 8/4$1,900
Sun 24/514:00
AKL
-
ORD
2 stops32h 59m
Multiple Airlines
Sun 31/507:15
ORD
-
AKL
2 stops36h 30m
Multiple Airlines
Deal found 9/4$1,954
Mon 11/514:00
AKL
-
ORD
2 stops33h 39m
Multiple Airlines
Wed 20/520:56
ORD
-
AKL
1 stop40h 04m
Multiple Airlines
Deal found 7/4$2,015
Fri 22/516:25
AKL
-
ORD
1 stop34h 23m
American Airlines
Fri 29/518:59
ORD
-
AKL
2 stops26h 11m
American Airlines
Deal found 7/4$2,097

Find flight deals to Chicago

Find the latest flights to Chicago in 2026, 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 11 April 2026.

Return from

$1,671

One-way from

$929

Popular in

August

Cheapest in

February

Average price

$1,986
American Airlines
  • American Airlines
  • 11/5-26/5
  • 3 total stops
  • 62h 36m total
  • Auckland to Chicago
Search Deals
15/5
  • 15/5
  • 2 total stops
  • 32h 59m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($315 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($33 potential savings vs. average return price).
Search Deals
Average for return flights in April 2026
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 11 April 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Departure

Return

Price

Cheapest return flight

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 11/5

08:20-19:57

2 stops28h 37m

Chicago O'Hare Intl

Fri 22/5

17:10-14:05

2 stops27h 55m

$2,479

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 12/5

15:55-14:16

2 stops39h 21m

Chicago O'Hare Intl

Mon 25/5

18:59-14:10

2 stops26h 11m

$2,563

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 12/5

08:20-19:57

2 stops28h 37m

Chicago O'Hare Intl

Wed 20/5

19:21-14:10

2 stops25h 49m

$2,563

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 12/5

08:20-19:57

2 stops28h 37m

Chicago O'Hare Intl

Sun 24/5

11:45-14:05

2 stops33h 20m

$2,563

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 12/5

08:20-17:44

2 stops26h 24m

Chicago O'Hare Intl

Thu 21/5

18:59-14:05

2 stops26h 06m

$2,593

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 13/5

08:20-17:44

2 stops26h 24m

Chicago O'Hare Intl

Fri 22/5

18:59-14:05

2 stops26h 06m

$2,593

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 17/5

20:15-01:18

1 stop22h 03m

Chicago O'Hare Intl

Sun 24/5

14:21-06:00

1 stop22h 39m

$2,735

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 3/6

19:50-00:45

1 stop21h 55m

Chicago O'Hare Intl

Sun 7/6

07:00-06:00

1 stop30h 00m

$2,758
Fastest return journey

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 19/8

19:50-21:37

1 stop18h 47m

Chicago O'Hare Intl

Tue 25/8

13:58-06:00

1 stop23h 02m

$2,759

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 31/8

20:15-23:10

1 stop19h 55m

Chicago O'Hare Intl

Sat 5/9

21:40-06:00

2 stops39h 20m

$2,761

Flights are sorted by cheapest return flights first.

Deals found on 8/4

Showing 1-10 of 18 resultsSorted by cheapest first
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 10 April 2026.

The best time to book flights to Chicago is 86 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 34 hours 14 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.

What are the most popular airlines that fly to Chicago?

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

Air New Zealand
Air New Zealand
From $1,617
Qantas Airways
Qantas Airways
From $1,412
United Airlines
United Airlines
From $1,411

What are the cheapest airlines that fly to Chicago?

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

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 11 April 2026.
Read reviews from past customers who have flown Fiji Airways,Air New Zealand, andQantas Airways 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.
Fiji Airways
8.1
Very Good
239 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Comfort

8.1

Entertainment

7.5

Reviews

1 / 19
8.0
Excellent

Paul,Mar 2026

YVR - NAN

Flown with Fiji Airways before they have always been good. The crew are very friendly and attentive. The seats in economy are in the small side but good. Another happy flight with them.
Fiji Airways
8.1
Very Good
239 reviews
Fiji Airways
8.1
Very Good
239 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Comfort

8.1

Entertainment

7.5

Reviews

1 / 19
8.0
Excellent

Paul,Mar 2026

YVR - NAN

Flown with Fiji Airways before they have always been good. The crew are very friendly and attentive. The seats in economy are in the small side but good. Another happy flight with them.
Air New Zealand
8.0
Very Good
627 reviews
Fiji Airways
8.1
Very Good
239 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Comfort

8.1

Entertainment

7.5

Reviews

1 / 19
8.0
Excellent

Paul,Mar 2026

YVR - NAN

Flown with Fiji Airways before they have always been good. The crew are very friendly and attentive. The seats in economy are in the small side but good. Another happy flight with them.
Qantas Airways
7.5
Good
1,018 reviews
Fiji Airways
8.1
Very Good
239 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Comfort

8.1

Entertainment

7.5

Reviews

1 / 19
8.0
Excellent

Paul,Mar 2026

YVR - NAN

Flown with Fiji Airways before they have always been good. The crew are very friendly and attentive. The seats in economy are in the small side but good. Another happy flight with them.
United Airlines
7.4
Good
9,571 reviews
Fiji Airways
8.1
Very Good
239 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Comfort

8.1

Entertainment

7.5

Reviews

1 / 19
8.0
Excellent

Paul,Mar 2026

YVR - NAN

Flown with Fiji Airways before they have always been good. The crew are very friendly and attentive. The seats in economy are in the small side but good. Another happy flight with them.
Air Canada
7.1
Good
10,916 reviews
Fiji Airways
8.1
Very Good
239 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Comfort

8.1

Entertainment

7.5

Reviews

1 / 19
8.0
Excellent

Paul,Mar 2026

YVR - NAN

Flown with Fiji Airways before they have always been good. The crew are very friendly and attentive. The seats in economy are in the small side but good. Another happy flight with them.

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 $384, while return flights cost around $690.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $733, however they can be found for as little as $690.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Wellington offers the quickest one-way flight (29 hours 6 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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