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$668+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
29 Mar — 5 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 27 February 2026.

Thu 9/414:00
AKL
-
ORD
3 stops41h 16m
Multiple Airlines
Thu 16/407:55
ORD
-
AKL
3 stops35h 50m
Multiple Airlines
Deal found 23/2$1,716
Wed 8/414:00
AKL
-
ORD
3 stops41h 16m
Multiple Airlines
Wed 22/407:55
ORD
-
AKL
3 stops47h 35m
Multiple Airlines
Deal found 24/2$1,741
Mon 20/414:00
AKL
-
ORD
2 stops34h 00m
Multiple Airlines
Sat 25/407:55
ORD
-
AKL
3 stops35h 50m
Multiple Airlines
Deal found 24/2$1,772
Fri 20/1106:15
AKL
-
ORD
2 stops27h 26m
Air Canada
Mon 30/1115:40
ORD
-
AKL
2 stops30h 40m
Air Canada
Deal found 24/2$1,787
Thu 19/312:20
AKL
-
ORD
2 stops38h 42m
American Airlines
Mon 23/312:15
ORD
-
AKL
2 stops25h 55m
American Airlines
Deal found 23/2$1,798
Wed 18/314:50
AKL
-
ORD
1 stop24h 47m
Air New Zealand
Fri 20/319:50
ORD
-
AKL
1 stop39h 55m
Air New Zealand
Deal found 25/2$1,928
Wed 18/313:35
AKL
-
ORD
2 stops22h 30m
Delta
Fri 20/313:19
ORD
-
AKL
2 stops24h 16m
Delta
Deal found 25/2$1,930
Mon 20/413:00
AKL
-
ORD
2 stops20h 18m
Delta
Sat 25/407:35
ORD
-
AKL
2 stops30h 15m
Delta
Deal found 24/2$1,934
Sat 21/1114:35
AKL
-
ORD
2 stops24h 49m
Delta
Sun 29/1114:55
ORD
-
AKL
1 stop22h 40m
Delta
Deal found 24/2$1,937
Wed 18/319:30
AKL
-
ORD
2 stops37h 11m
Multiple Airlines
Fri 20/315:35
ORD
-
AKL
1 stop24h 25m
Multiple Airlines
Deal found 25/2$1,959
Sat 21/1120:10
AKL
-
ORD
1 stop21h 52m
Air New Zealand
Sun 6/1214:10
ORD
-
AKL
1 stop19h 50m
Air New Zealand
Deal found 24/2$1,985

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 27 February 2026.

Return from

$1,716

One-way from

$668

Popular in

July

Cheapest in

November

Average price

$1,531
9/4-16/4
  • 9/4-16/4
  • 6 total stops
  • 77h 06m total
  • Auckland to Chicago
Search Deals
6/5
  • 6/5
  • 2 total stops
  • 32h 50m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($185 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 February 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 27 February 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Departure

Return

Price

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 18/3

13:35-18:05

2 stops22h 30m

Chicago O'Hare Intl

Fri 20/3

13:19-07:35

2 stops24h 16m

$1,930

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 20/4

13:00-16:18

2 stops20h 18m

Chicago O'Hare Intl

Sat 25/4

07:35-06:50

2 stops30h 15m

$1,934

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 1/8

13:50-20:27

2 stops23h 37m

Chicago O'Hare Intl

Tue 19/1

08:55-06:05

2 stops26h 10m

$2,029

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 30/6

13:25-23:59

2 stops27h 34m

Chicago O'Hare Intl

Sun 12/7

17:10-14:05

2 stops27h 55m

$2,333

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 2/7

06:00-14:18

2 stops25h 18m

Chicago O'Hare Intl

Sun 19/7

19:00-14:05

2 stops26h 05m

$2,351

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 2/7

13:50-00:59

1 stop28h 09m

Chicago O'Hare Intl

Sun 12/7

07:00-05:00

1 stop29h 00m

$2,393

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 1/7

20:15-23:16

1 stop20h 01m

Chicago O'Hare Intl

Sun 12/7

07:00-05:00

1 stop29h 00m

$3,104

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 2/7

16:30-17:04

3 stops41h 34m

Chicago O'Hare Intl

Sat 18/7

00:30-14:45

2 stops45h 15m

$3,226

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 7/5

13:00-20:26

2 stops24h 26m

$863

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 17/3

20:40-05:18

1 stop26h 38m

$870

Flights are sorted by cheapest return flights first.

Deals found on 24/2

Showing 1-10 of 15 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 20 February 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 28 hours 13 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 $1,578
Qantas Airways
Qantas Airways
From $1,334
United Airlines
United Airlines
From $1,377

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Qantas Airways, United Airlines 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 27 February 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
8.0
Very Good
228 reviews
Check prices

Food

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.5

Reviews

1 / 18
10.0
Excellent

Anonymous,Feb 2026

SFO - NAN

Very friendly staff, warm service, well maintained aircraft, comfortable seats, and reliable on-time performance 👍👍
Fiji Airways
8.0
Very Good
228 reviews
Fiji Airways
8.0
Very Good
228 reviews
Check prices

Food

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.5

Reviews

1 / 18
10.0
Excellent

Anonymous,Feb 2026

SFO - NAN

Very friendly staff, warm service, well maintained aircraft, comfortable seats, and reliable on-time performance 👍👍
Air New Zealand
8.0
Very Good
605 reviews
Fiji Airways
8.0
Very Good
228 reviews
Check prices

Food

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.5

Reviews

1 / 18
10.0
Excellent

Anonymous,Feb 2026

SFO - NAN

Very friendly staff, warm service, well maintained aircraft, comfortable seats, and reliable on-time performance 👍👍
Qantas Airways
7.5
Good
999 reviews
Fiji Airways
8.0
Very Good
228 reviews
Check prices

Food

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.5

Reviews

1 / 18
10.0
Excellent

Anonymous,Feb 2026

SFO - NAN

Very friendly staff, warm service, well maintained aircraft, comfortable seats, and reliable on-time performance 👍👍
United Airlines
7.4
Good
9,351 reviews
Fiji Airways
8.0
Very Good
228 reviews
Check prices

Food

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.5

Reviews

1 / 18
10.0
Excellent

Anonymous,Feb 2026

SFO - NAN

Very friendly staff, warm service, well maintained aircraft, comfortable seats, and reliable on-time performance 👍👍
Air Canada
7.1
Good
10,750 reviews
Fiji Airways
8.0
Very Good
228 reviews
Check prices

Food

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.5

Reviews

1 / 18
10.0
Excellent

Anonymous,Feb 2026

SFO - NAN

Very friendly staff, warm service, well maintained aircraft, comfortable seats, and reliable on-time performance 👍👍

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 $149, while return flights cost around $145.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $175, however they can be found for as little as $145.

  • 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 (25 hours 27 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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When you search for this flight to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

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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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