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$1,028+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
20 Jul — 27 Jul1
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 20 June 2026.

Mon 27/716:25
AKL
-
ORD
1 stop34h 37m
American Airlines
Mon 10/819:00
ORD
-
AKL
2 stops28h 50m
American Airlines
Deal found 15/6$1,799
Wed 22/716:25
AKL
-
ORD
1 stop34h 37m
American Airlines
Fri 31/719:08
ORD
-
AKL
2 stops25h 57m
American Airlines
Deal found 15/6$1,855
Mon 3/820:15
AKL
-
ORD
1 stop25h 36m
Air New Zealand
Mon 10/806:00
ORD
-
AKL
1 stop31h 00m
Air New Zealand
Deal found 19/6$2,006
Mon 7/919:50
AKL
-
ORD
1 stop28h 06m
Air New Zealand
Mon 14/916:40
ORD
-
AKL
1 stop20h 20m
Air New Zealand
Deal found 15/6$2,027
Mon 3/820:15
AKL
-
ORD
1 stop27h 02m
Multiple Airlines
Mon 10/821:13
ORD
-
AKL
2 stops46h 32m
Multiple Airlines
Deal found 19/6$2,072
Mon 13/713:25
AKL
-
ORD
2 stops27h 42m
American Airlines
Mon 27/719:08
ORD
-
AKL
2 stops26h 02m
American Airlines
Deal found 19/6$2,090
Sun 22/1114:35
AKL
-
ORD
1 stop27h 55m
Delta
Sun 29/1107:10
ORD
-
AKL
2 stops30h 05m
Delta
Deal found 17/6$2,107
Tue 8/920:15
AKL
-
ORD
2 stops20h 44m
United Airlines
Sun 13/905:55
ORD
-
AKL
1 stop31h 05m
United Airlines
Deal found 15/6$2,111
Wed 22/720:15
AKL
-
ORD
1 stop22h 00m
United Airlines
Fri 31/721:30
ORD
-
AKL
1 stop39h 30m
United Airlines
Deal found 18/6$2,132
Mon 7/919:50
AKL
-
ORD
1 stop21h 52m
Multiple Airlines
Thu 17/914:46
ORD
-
AKL
1 stop21h 44m
Multiple Airlines
Deal found 15/6$2,137
Sat 5/920:15
AKL
-
ORD
2 stops20h 44m
United Airlines
Mon 14/915:48
ORD
-
AKL
1 stop21h 12m
United Airlines
Deal found 15/6$2,142

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 20 June 2026.

Return from

$1,799

One-way from

$1,028

Popular in

June

Cheapest in

February

Average price

$2,705
American Airlines
  • American Airlines
  • 27/7-10/8
  • 3 total stops
  • 63h 27m total
  • Auckland to Chicago
Search Deals
9/9
  • 9/9
  • 3 total stops
  • 39h 02m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($331 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($48 potential savings vs. average return price).
Search Deals
Average for return flights in June 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 20 June 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 3/8

20:15-04:51

1 stop25h 36m

Chicago O'Hare Intl

Mon 10/8

06:00-06:00

1 stop31h 00m

$2,006

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 22/11

14:35-23:30

1 stop27h 55m

Chicago O'Hare Intl

Sun 29/11

07:10-08:15

2 stops30h 05m

$2,107

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 9/9

19:50-00:59

1 stop22h 09m

Chicago O'Hare Intl

Wed 16/9

17:53-05:30

1 stop18h 37m

$2,111

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 8/9

20:15-23:59

2 stops20h 44m

Chicago O'Hare Intl

Thu 17/9

16:40-06:00

1 stop20h 20m

$2,142

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 6/9

19:50-21:30

1 stop18h 40m

Chicago O'Hare Intl

Tue 15/9

16:20-07:10

1 stop21h 50m

$2,142

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 5/9

20:15-23:59

2 stops20h 44m

Chicago O'Hare Intl

Mon 14/9

15:48-06:00

1 stop21h 12m

$2,142
Fastest return journey

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 6/9

19:50-21:30

1 stop18h 40m

Chicago O'Hare Intl

Thu 17/9

15:48-06:00

1 stop21h 12m

$2,172

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 13/7

20:15-06:17

1 stop27h 02m

Chicago O'Hare Intl

Mon 27/7

21:13-12:45

2 stops46h 32m

$2,360

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 13/7

13:25-14:27

2 stops42h 02m

Chicago O'Hare Intl

Mon 27/7

15:21-14:05

2 stops29h 44m

$2,360

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 22/11

08:00-10:36

3 stops45h 36m

Chicago O'Hare Intl

Sun 29/11

09:18-13:35

3 stops33h 17m

$2,631

Flights are sorted by cheapest return flights first.

Deals found on 15/6

Showing 1-10 of 17 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

How long is the flight to Chicago?

On average, a flight from Auckland to Chicago takes 25 hours 36 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, American Airlines and Qantas Airways.

Air New Zealand
Air New Zealand
From $1,646
American Airlines
American Airlines
From $1,534
Qantas Airways
Qantas Airways
From $1,437
United Airlines
United Airlines
From $1,436

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are United Airlines, Qantas Airways and American 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 20 June 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
244 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.1

Comfort

8.1

Food

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
244 reviews
Fiji Airways
8.1
Very Good
244 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.1

Comfort

8.1

Food

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
645 reviews
Fiji Airways
8.1
Very Good
244 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.1

Comfort

8.1

Food

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
1,047 reviews
Fiji Airways
8.1
Very Good
244 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.1

Comfort

8.1

Food

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.
American Airlines
7.1
Good
11,716 reviews
Fiji Airways
8.1
Very Good
244 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.1

Comfort

8.1

Food

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
11,227 reviews
Fiji Airways
8.1
Very Good
244 reviews
Check prices

Boarding

8.2

Entertainment

7.5

Crew

8.5

Overall

8.1

Comfort

8.1

Food

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 $429, while return flights cost around $307.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $309, however they can be found for as little as $307.

  • 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 (23 hours 34 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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