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$932+ Cheap flights to Chicago

— CHI
24 Sep — 1 Oct1
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

Thu 5/1106:00 -
2 stops42h 02m
Mon 9/1121:06 -
2 stops65h 19m
Deal found 20/8$1,716
Sun 20/1215:50 -
1 stop39h 31m
Wed 30/1219:01 -
1 stop19h 24m
Deal found 24/8$2,018
Thu 8/1016:15 -
2 stops32h 19m
Thu 15/1020:01 -
2 stops50h 49m
Deal found 24/8$2,065
Thu 12/1116:05 -
2 stops26h 56m
Mon 23/1121:03 -
2 stops45h 37m
Deal found 23/8$2,273
Thu 12/1119:50 -
1 stop22h 36m
Mon 23/1111:59 -
1 stop24h 31m
Deal found 23/8$2,326
Mon 12/1006:00 -
2 stops27h 59m
Mon 26/1017:53 -
2 stops26h 52m
Deal found 24/8$2,341
Mon 12/1014:25 -
1 stop41h 30m
Mon 26/1015:35 -
1 stop27h 50m
Deal found 24/8$2,360
Sun 20/1216:05 -
2 stops39h 16m
Wed 30/1218:45 -
2 stops47h 55m
Deal found 24/8$2,365

Find flight deals to Chicago

Return from

$1,716

One-way from

$932

Popular in

June

Cheapest in

February

Average price

$2,330
American Airlines
  • American Airlines
  • 5/11-9/11
  • 4 total stops
  • 107h 21m total
  • Auckland to Chicago
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19/11
  • 19/11
  • 3 total stops
  • 25h 46m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($308 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease ($43 potential savings vs. average return price).
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Average for return flights in August 2026
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Cheapflights Fare Finder

 
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 Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

06:00-05:02

2 stops42h 02m

Chicago O'Hare Intl

Mon 9/11

21:06-09:25

2 stops65h 19m

$2,286

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 20/2

16:05-18:38

2 stops21h 33m

Chicago O'Hare Intl

Tue 2/3

13:50-13:40

2 stops28h 50m

$2,301

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sun 20/12

16:05-12:21

2 stops39h 16m

Chicago O'Hare Intl

Wed 30/12

18:45-13:40

2 stops47h 55m

$2,365

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 21/9

13:25-14:20

2 stops41h 55m

Chicago O'Hare Intl

Mon 28/9

19:03-15:05

2 stops26h 02m

$2,418
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 20/2

14:45-13:47

1 stop18h 02m

Chicago O'Hare Intl

Sun 28/2

18:30-08:55

1 stop19h 25m

$2,447

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

20:20-23:59

2 stops22h 39m

Chicago O'Hare Intl

Mon 9/11

16:01-09:10

1 stop22h 09m

$2,452

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 19/2

14:45-21:53

2 stops26h 08m

Chicago O'Hare Intl

Sat 27/2

18:30-08:55

1 stop19h 25m

$2,452

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 19/2

14:45-13:47

1 stop18h 02m

Chicago O'Hare Intl

Wed 3/3

18:59-08:55

2 stops42h 56m

$2,452

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 12/11

15:50-21:30

2 stops24h 40m

Chicago O'Hare Intl

Mon 23/11

18:20-09:10

1 stop19h 50m

$2,464
Cheapest one-way

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 21/10

21:10-06:34

3 stops51h 24m

$1,078

Flights are sorted by cheapest return flights first.

Deals found on 23/8

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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

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 2 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 $1,722
Qantas Airways
Qantas Airways
From $1,407
American Airlines
American Airlines
From $1,476

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Qantas Airways, American Airlines and Air New Zealand.

Rainfall in Chicago 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

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

Read reviews from past customers who have flown Air New Zealand,Qantas Airways, andUnited Airlines 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.
Air New Zealand
8.0
Very Good
664 reviews
Check prices

Comfort

7.9

Food

7.5

Crew

8.5

Entertainment

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Viren,Jun 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
Air New Zealand
8.0
Very Good
664 reviews
Air New Zealand
8.0
Very Good
664 reviews
Check prices

Comfort

7.9

Food

7.5

Crew

8.5

Entertainment

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Viren,Jun 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
Qantas Airways
7.5
Good
1,085 reviews
Air New Zealand
8.0
Very Good
664 reviews
Check prices

Comfort

7.9

Food

7.5

Crew

8.5

Entertainment

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Viren,Jun 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
United Airlines
7.4
Good
10,116 reviews
Air New Zealand
8.0
Very Good
664 reviews
Check prices

Comfort

7.9

Food

7.5

Crew

8.5

Entertainment

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Viren,Jun 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.
Air Canada
7.1
Good
11,526 reviews
Air New Zealand
8.0
Very Good
664 reviews
Check prices

Comfort

7.9

Food

7.5

Crew

8.5

Entertainment

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Viren,Jun 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

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 $289, 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 (19 hours 2 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

Browse thousands of different options on Cheapflights for your next trip

Airports serving Chicago

Flights to Midway
Flights to O'Hare Intl
Flights from Midway
Flights from O'Hare Intl

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