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$1,105+ 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 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
27 Jun — 4 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 28 May 2026.

Fri 13/1120:10
AKL
-
ORD
1 stop19h 12m
Air New Zealand
Wed 25/1115:51
ORD
-
AKL
1 stop19h 14m
Air New Zealand
Deal found 26/5$2,315
Thu 11/613:50
AKL
-
ORD
1 stop33h 03m
United Airlines
Sat 13/605:30
ORD
-
AKL
1 stop31h 00m
United Airlines
Deal found 26/5$2,362
Tue 16/606:10
AKL
-
ORD
2 stops26h 39m
Qantas Airways
Fri 26/618:59
ORD
-
AKL
2 stops26h 11m
Qantas Airways
Deal found 26/5$2,376
Fri 13/1108:20
AKL
-
ORD
2 stops26h 35m
Qantas Airways
Wed 25/1115:00
ORD
-
AKL
2 stops28h 05m
Qantas Airways
Deal found 26/5$2,384
Tue 23/613:25
AKL
-
ORD
2 stops43h 24m
Qantas Airways
Tue 30/618:59
ORD
-
AKL
2 stops28h 51m
Qantas Airways
Deal found 25/5$2,447
Sun 14/615:35
AKL
-
ORD
2 stops32h 40m
Air Tahiti Nui
Tue 17/1118:03
ORD
-
AKL
2 stops24h 37m
Air Tahiti Nui
Deal found 27/5$2,449
Thu 17/906:10
AKL
-
ORD
2 stops26h 40m
Qantas Airways
Mon 21/918:02
ORD
-
AKL
2 stops27h 03m
Qantas Airways
Deal found 24/5$2,452
Mon 22/608:20
AKL
-
ORD
2 stops28h 08m
Qantas Airways
Wed 1/718:20
ORD
-
AKL
2 stops26h 50m
Qantas Airways
Deal found 26/5$2,454
Sun 14/615:35
AKL
-
ORD
2 stops32h 40m
Air Tahiti Nui
Mon 16/1120:40
ORD
-
AKL
2 stops46h 00m
Air Tahiti Nui
Deal found 27/5$2,457
Wed 26/813:25
AKL
-
ORD
2 stops27h 05m
American Airlines
Sun 30/815:21
ORD
-
AKL
2 stops29h 44m
American Airlines
Deal found 27/5$2,461
Thu 3/913:25
AKL
-
ORD
2 stops45h 22m
Qantas Airways
Thu 10/915:52
ORD
-
AKL
2 stops29h 13m
Qantas Airways
Deal found 24/5$2,464
Thu 16/714:00
AKL
-
ORD
2 stops24h 22m
Multiple Airlines
Thu 30/718:19
ORD
-
AKL
2 stops25h 26m
Multiple Airlines
Deal found 24/5$2,481

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 28 May 2026.

Return from

$2,315

One-way from

$1,154

Popular in

May

Cheapest in

February

Average price

$2,731
Air New Zealand
  • Air New Zealand
  • 13/11-25/11
  • 2 total stops
  • 38h 26m total
  • Auckland to Chicago
Search Deals
14/7
  • 14/7
  • 2 total stops
  • 43h 08m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($239 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($61 potential savings vs. average return price).
Search Deals
Average for return flights in May 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 28 May 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

Thu 16/7

14:00-21:22

2 stops24h 22m

Chicago O'Hare Intl

Thu 30/7

18:19-12:45

2 stops25h 26m

$2,481

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 17/7

13:25-00:07

2 stops27h 42m

Chicago O'Hare Intl

Fri 31/7

19:08-14:10

2 stops26h 02m

$2,512

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 17/9

10:15-13:55

1 stop44h 40m

Chicago O'Hare Intl

Mon 21/9

16:15-19:10

2 stops33h 55m

$2,515

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 11/6

13:50-16:38

1 stop19h 48m

Chicago O'Hare Intl

Sat 14/11

21:30-06:05

1 stop37h 35m

$2,639

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 11/6

13:50-14:50

1 stop18h 00m

Chicago O'Hare Intl

Wed 11/11

12:45-09:10

2 stops25h 25m

$2,639

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 26/6

08:20-19:28

2 stops28h 08m

Chicago O'Hare Intl

Sun 12/7

18:18-14:05

2 stops26h 47m

$2,641

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 15/6

13:50-00:59

1 stop28h 09m

Chicago O'Hare Intl

Thu 12/11

15:51-06:05

1 stop19h 14m

$2,670
Fastest return journey

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 10/7

19:00-00:45

2 stops22h 45m

Chicago O'Hare Intl

Fri 17/7

17:45-05:30

1 stop18h 45m

$2,806

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 23/6

07:00-14:50

2 stops24h 50m

Chicago O'Hare Intl

Tue 30/6

07:00-05:00

1 stop29h 00m

$3,021

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 3/9

15:15-12:09

3 stops37h 54m

Chicago O'Hare Intl

Thu 10/9

15:40-12:45

2 stops28h 05m

$3,028

Flights are sorted by cheapest return flights first.

Deals found on 28/5

Showing 1-10 of 22 resultsSorted by cheapest first
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2
3

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 19 hours 12 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 American Airlines.

Air New Zealand
Air New Zealand
From $1,906
Qantas Airways
Qantas Airways
From $1,305
American Airlines
American Airlines
From $1,496
United Airlines
United Airlines
From $1,401

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Qantas Airways, United Airlines 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 28 May 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
243 reviews
Check prices

Overall

8.1

Boarding

8.2

Food

7.5

Comfort

8.1

Entertainment

7.5

Crew

8.6

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
243 reviews
Fiji Airways
8.1
Very Good
243 reviews
Check prices

Overall

8.1

Boarding

8.2

Food

7.5

Comfort

8.1

Entertainment

7.5

Crew

8.6

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
648 reviews
Fiji Airways
8.1
Very Good
243 reviews
Check prices

Overall

8.1

Boarding

8.2

Food

7.5

Comfort

8.1

Entertainment

7.5

Crew

8.6

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
1,043 reviews
Fiji Airways
8.1
Very Good
243 reviews
Check prices

Overall

8.1

Boarding

8.2

Food

7.5

Comfort

8.1

Entertainment

7.5

Crew

8.6

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
9,751 reviews
Fiji Airways
8.1
Very Good
243 reviews
Check prices

Overall

8.1

Boarding

8.2

Food

7.5

Comfort

8.1

Entertainment

7.5

Crew

8.6

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
11,095 reviews
Fiji Airways
8.1
Very Good
243 reviews
Check prices

Overall

8.1

Boarding

8.2

Food

7.5

Comfort

8.1

Entertainment

7.5

Crew

8.6

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, Qantas Airways 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 $419, while return flights cost around $299.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $301, however they can be found for as little as $299.

  • 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 12 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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Yes, we can. To see specific flights to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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