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$1,080+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
7 Jun — 14 Jun1
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 8 May 2026.

Tue 2/615:15
AKL
-
ORD
1 stop21h 35m
Air Tahiti Nui
Tue 16/608:05
ORD
-
AKL
2 stops35h 05m
Air Tahiti Nui
Deal found 7/5$2,145
Fri 23/1006:00
AKL
-
ORD
2 stops42h 01m
American Airlines
Tue 27/1018:35
ORD
-
AKL
2 stops43h 50m
American Airlines
Deal found 5/5$2,187
Tue 2/613:25
AKL
-
ORD
2 stops27h 34m
Qantas Airways
Tue 16/618:59
ORD
-
AKL
2 stops26h 06m
Qantas Airways
Deal found 7/5$2,256
Fri 24/716:25
AKL
-
ORD
1 stop34h 37m
American Airlines
Thu 30/719:08
ORD
-
AKL
2 stops26h 02m
American Airlines
Deal found 4/5$2,313
Mon 11/513:50
AKL
-
ORD
1 stop32h 50m
United Airlines
Wed 13/505:30
ORD
-
AKL
1 stop31h 00m
United Airlines
Deal found 7/5$2,336
Fri 17/706:45
AKL
-
ORD
2 stops34h 22m
Qantas Airways
Fri 24/719:08
ORD
-
AKL
2 stops26h 02m
Qantas Airways
Deal found 8/5$2,380
Tue 1/906:10
AKL
-
ORD
2 stops27h 34m
Qantas Airways
Sun 1/1114:54
ORD
-
AKL
1 stop23h 31m
Qantas Airways
Deal found 5/5$2,415

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 8 May 2026.

Return from

$2,145

One-way from

$1,080

Popular in

July

Cheapest in

February

Average price

$2,110
Air Tahiti Nui
  • Air Tahiti Nui
  • 2/6-16/6
  • 3 total stops
  • 56h 40m total
  • Auckland to Chicago
Search Deals
12/8
  • 12/8
  • 3 total stops
  • 32h 28m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($235 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($31 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 8 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

Mon 15/6

13:25-23:58

2 stops27h 33m

Chicago O'Hare Intl

Sun 21/6

18:59-14:05

2 stops26h 06m

$2,424

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 1/6

06:10-15:52

2 stops26h 42m

Chicago O'Hare Intl

Mon 8/6

15:50-12:15

2 stops27h 25m

$2,427

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 1/9

06:10-16:44

2 stops27h 34m

Chicago O'Hare Intl

Sun 1/11

14:54-14:05

2 stops28h 11m

$2,430

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 7/6

16:25-10:30

1 stop35h 05m

Chicago O'Hare Intl

Thu 18/6

15:23-14:10

2 stops29h 47m

$2,435

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 19/6

08:20-19:28

2 stops28h 08m

Chicago O'Hare Intl

Fri 26/6

18:59-14:10

2 stops26h 11m

$2,491

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 26/6

06:00-23:58

2 stops34h 58m

Chicago O'Hare Intl

Sun 12/7

19:08-14:05

2 stops25h 57m

$2,705

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 1/6

13:50-22:49

2 stops25h 59m

Chicago O'Hare Intl

Mon 8/6

15:47-06:00

1 stop21h 13m

$2,833

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 7/6

19:50-11:29

1 stop32h 39m

Chicago O'Hare Intl

Thu 18/6

18:20-07:10

1 stop19h 50m

$2,838

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 17/7

19:00-06:17

1 stop28h 17m

Chicago O'Hare Intl

Fri 24/7

21:13-13:20

2 stops47h 07m

$2,910
Fastest return journey

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 18/6

20:15-04:51

1 stop25h 36m

Chicago O'Hare Intl

Thu 25/6

18:20-07:10

1 stop19h 50m

$3,370

Flights are sorted by cheapest return flights first.

Deals found on 3/5

Showing 1-10 of 22 resultsSorted by cheapest first
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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?

The best time to book flights to Chicago is 73 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 21 hours 35 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 $1,586
Qantas Airways
Qantas Airways
From $1,384
United Airlines
United Airlines
From $1,383
American Airlines
American Airlines
From $1,477

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 8 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
240 reviews
Check prices

Crew

8.6

Entertainment

7.5

Boarding

8.2

Food

7.5

Comfort

8.1

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
240 reviews
Fiji Airways
8.1
Very Good
240 reviews
Check prices

Crew

8.6

Entertainment

7.5

Boarding

8.2

Food

7.5

Comfort

8.1

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
640 reviews
Fiji Airways
8.1
Very Good
240 reviews
Check prices

Crew

8.6

Entertainment

7.5

Boarding

8.2

Food

7.5

Comfort

8.1

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
1,033 reviews
Fiji Airways
8.1
Very Good
240 reviews
Check prices

Crew

8.6

Entertainment

7.5

Boarding

8.2

Food

7.5

Comfort

8.1

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
9,694 reviews
Fiji Airways
8.1
Very Good
240 reviews
Check prices

Crew

8.6

Entertainment

7.5

Boarding

8.2

Food

7.5

Comfort

8.1

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
11,003 reviews
Fiji Airways
8.1
Very Good
240 reviews
Check prices

Crew

8.6

Entertainment

7.5

Boarding

8.2

Food

7.5

Comfort

8.1

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 $219, while return flights cost around $295.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $297, however they can be found for as little as $295.

  • 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 (21 hours 35 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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