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$872+ Cheap flights to Chicago

— CHI
30 Sep — 7 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 22/1019:50 -
1 stop31h 19m
Sat 24/1008:50 -
1 stop27h 10m
Deal found 28/8$1,896
Thu 8/1016:15 -
2 stops32h 19m
Thu 22/1020:01 -
2 stops51h 54m
Deal found 27/8$2,000
Tue 13/1006:15 -
2 stops26h 28m
Tue 20/1008:49 -
2 stops36h 01m
Deal found 28/8$2,096
Mon 12/1007:45 -
2 stops34h 45m
Tue 27/1016:25 -
1 stop42h 30m
Deal found 29/8$2,128
Tue 13/1020:15 -
1 stop28h 19m
Tue 20/1020:01 -
2 stops48h 04m
Deal found 28/8$2,135
Mon 19/1006:15 -
2 stops26h 28m
Wed 4/1108:49 -
2 stops37h 36m
Deal found 30/8$2,152
Mon 19/1017:25 -
1 stop33h 40m
Wed 4/1115:22 -
2 stops22h 48m
Deal found 27/8$2,158
Mon 19/1017:25 -
1 stop33h 40m
Wed 4/1113:22 -
2 stops24h 48m
Deal found 30/8$2,179

Find flight deals to Chicago

Return from

$1,896

One-way from

$872

Popular in

May

Cheapest in

November

Average price

$2,566
United Airlines
  • United Airlines
  • 22/10-24/10
  • 3 total stops
  • 58h 40m total
  • Auckland to Chicago
Search Deals
2/11
  • 2/11
  • 3 total stops
  • 33h 23m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($287 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($59 potential savings vs. average return price).
Search Deals
Average for return flights in August 2026
Search Deals

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 22/10

19:50-09:09

1 stop31h 19m

Chicago O'Hare Intl

Sat 24/10

08:50-06:00

1 stop27h 10m

$1,896

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 19/10

17:25-09:05

1 stop33h 40m

Chicago O'Hare Intl

Wed 4/11

15:22-09:10

2 stops22h 48m

$2,158

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

07:30-16:05

2 stops27h 35m

Chicago O'Hare Intl

Mon 9/11

20:00-09:10

2 stops66h 10m

$2,179
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

19:50-23:26

1 stop22h 36m

Chicago O'Hare Intl

Mon 9/11

16:01-09:10

1 stop22h 09m

$2,358

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 13/10

20:15-05:15

1 stop27h 00m

Chicago O'Hare Intl

Tue 20/10

15:50-06:00

1 stop20h 10m

$2,371

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 21/10

20:15-22:46

2 stops20h 31m

Chicago O'Hare Intl

Thu 5/11

13:30-09:10

2 stops24h 40m

$2,402
Cheapest one-way

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 2/11

14:50-05:13

3 stops33h 23m

$872

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 25/11

14:50-23:59

3 stops28h 09m

$1,107

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 15/9

15:15-20:00

2 stops21h 45m

$1,127

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 20/11

14:45-23:54

2 stops28h 09m

$1,193

Flights are sorted by cheapest return flights first.

Deals found on 27/8

Showing 1-10 of 17 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

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 22 hours 39 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 $1,736
Qantas Airways
Qantas Airways
From $1,395
American Airlines
American Airlines
From $1,488

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
665 reviews
Check prices

Food

7.5

Overall

8.0

Entertainment

7.4

Crew

8.5

Comfort

7.9

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
665 reviews
Air New Zealand
8.0
Very Good
665 reviews
Check prices

Food

7.5

Overall

8.0

Entertainment

7.4

Crew

8.5

Comfort

7.9

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
1,087 reviews
Air New Zealand
8.0
Very Good
665 reviews
Check prices

Food

7.5

Overall

8.0

Entertainment

7.4

Crew

8.5

Comfort

7.9

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
10,148 reviews
Air New Zealand
8.0
Very Good
665 reviews
Check prices

Food

7.5

Overall

8.0

Entertainment

7.4

Crew

8.5

Comfort

7.9

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
11,559 reviews
Air New Zealand
8.0
Very Good
665 reviews
Check prices

Food

7.5

Overall

8.0

Entertainment

7.4

Crew

8.5

Comfort

7.9

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 $292, while return flights cost around $298.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $300, however they can be found for as little as $298.

  • 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 (22 hours 39 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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