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$931+ 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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
22 Apr — 29 Apr1
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 23 March 2026.

Mon 20/407:00
AKL
-
ORD
2 stops33h 27m
Multiple Airlines
Mon 27/414:00
ORD
-
AKL
2 stops40h 15m
Multiple Airlines
Deal found 23/3$1,654
Thu 14/514:00
AKL
-
ORD
2 stops26h 27m
Multiple Airlines
Thu 28/505:15
ORD
-
AKL
2 stops49h 00m
Multiple Airlines
Deal found 19/3$1,762
Sun 3/514:00
AKL
-
ORD
2 stops32h 35m
Multiple Airlines
Sun 10/505:15
ORD
-
AKL
2 stops38h 30m
Multiple Airlines
Deal found 18/3$1,865
Tue 5/514:00
AKL
-
ORD
2 stops25h 04m
Multiple Airlines
Tue 12/507:30
ORD
-
AKL
2 stops46h 45m
Multiple Airlines
Deal found 21/3$1,894
Fri 17/414:00
AKL
-
ORD
2 stops32h 35m
Multiple Airlines
Fri 24/405:15
ORD
-
AKL
2 stops49h 00m
Multiple Airlines
Deal found 20/3$1,937
Wed 6/514:00
AKL
-
ORD
2 stops32h 35m
Multiple Airlines
Wed 13/507:30
ORD
-
AKL
2 stops36h 15m
Multiple Airlines
Deal found 22/3$2,006

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 23 March 2026.

Return from

$1,654

One-way from

$931

Popular in

September

Cheapest in

February

Average price

$1,982
20/4-27/4
  • 20/4-27/4
  • 4 total stops
  • 73h 42m total
  • Auckland to Chicago
Search Deals
21/4
  • 21/4
  • 2 total stops
  • 39h 50m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($164 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($29 potential savings vs. average return price).
Search Deals
Average for return flights in March 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 23 March 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

Wed 6/5

14:00-05:35

2 stops32h 35m

Chicago O'Hare Intl

Wed 13/5

07:30-12:45

2 stops36h 15m

$2,006

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 14/5

15:15-21:35

2 stops23h 20m

Chicago O'Hare Intl

Thu 28/5

20:50-12:10

2 stops46h 20m

$2,043

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 1/8

06:10-18:06

2 stops28h 56m

Chicago O'Hare Intl

Wed 7/10

18:02-14:05

2 stops26h 03m

$2,491
Fastest return journey

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 11/6

19:50-00:45

1 stop21h 55m

Chicago O'Hare Intl

Tue 30/6

12:56-07:10

2 stops25h 14m

$2,633

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 12/6

06:10-15:52

2 stops26h 42m

Chicago O'Hare Intl

Wed 1/7

18:59-14:10

2 stops26h 11m

$2,657

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 1/8

13:50-21:39

2 stops24h 49m

Chicago O'Hare Intl

Wed 7/10

09:25-05:30

1 stop26h 05m

$2,661

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 12/6

19:50-11:04

2 stops32h 14m

Chicago O'Hare Intl

Wed 8/7

17:45-05:30

1 stop18h 45m

$2,722

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 12/6

19:50-11:04

2 stops32h 14m

Chicago O'Hare Intl

Sun 5/7

20:04-06:00

1 stop40h 56m

$2,722

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 26/6

19:50-23:15

1 stop20h 25m

Chicago O'Hare Intl

Sun 12/7

07:00-05:00

1 stop29h 00m

$2,724

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 12/6

19:50-11:04

2 stops32h 14m

Chicago O'Hare Intl

Thu 9/7

23:00-06:00

1 stop38h 00m

$2,752

Flights are sorted by cheapest return flights first.

Deals found on 19/3

Showing 1-10 of 16 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 13 March 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 23 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 $1,621
Qantas Airways
Qantas Airways
From $1,415
United Airlines
United Airlines
From $1,414

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 23 March 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
235 reviews
Check prices

Entertainment

7.5

Food

7.5

Crew

8.5

Comfort

8.1

Boarding

8.2

Overall

8.1

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
235 reviews
Fiji Airways
8.1
Very Good
235 reviews
Check prices

Entertainment

7.5

Food

7.5

Crew

8.5

Comfort

8.1

Boarding

8.2

Overall

8.1

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
618 reviews
Fiji Airways
8.1
Very Good
235 reviews
Check prices

Entertainment

7.5

Food

7.5

Crew

8.5

Comfort

8.1

Boarding

8.2

Overall

8.1

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
1,009 reviews
Fiji Airways
8.1
Very Good
235 reviews
Check prices

Entertainment

7.5

Food

7.5

Crew

8.5

Comfort

8.1

Boarding

8.2

Overall

8.1

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
9,463 reviews
Fiji Airways
8.1
Very Good
235 reviews
Check prices

Entertainment

7.5

Food

7.5

Crew

8.5

Comfort

8.1

Boarding

8.2

Overall

8.1

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
10,835 reviews
Fiji Airways
8.1
Very Good
235 reviews
Check prices

Entertainment

7.5

Food

7.5

Crew

8.5

Comfort

8.1

Boarding

8.2

Overall

8.1

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 $288, while return flights cost around $149.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $180, however they can be found for as little as $149.

  • 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 (23 hours 14 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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