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$992+ Cheap flights to Chicago

— CHI
3 Nov — 10 Nov1
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

Mon 9/1108:00 -
3 stops35h 21m
Tue 17/1106:30 -
3 stops46h 55m
Deal found 29/9$1,857
Mon 9/1108:00 -
3 stops35h 21m
Wed 18/1106:30 -
3 stops46h 55m
Deal found 29/9$1,867
Tue 10/1108:00 -
3 stops35h 21m
Wed 18/1106:30 -
3 stops46h 55m
Deal found 29/9$1,942
Tue 10/1108:00 -
3 stops35h 21m
Tue 17/1106:30 -
3 stops46h 55m
Deal found 29/9$1,987
Mon 2/1114:50 -
3 stops33h 23m
Sun 15/1106:30 -
2 stops28h 20m
Deal found 29/9$2,063
Wed 11/1114:50 -
3 stops28h 31m
Wed 18/1106:30 -
3 stops46h 55m
Deal found 29/9$2,108

Find flight deals to Chicago

Return from

$1,857

One-way from

$992

Popular in

May

Cheapest in

November

Average price

$2,535
9/11-17/11
  • 9/11-17/11
  • 6 total stops
  • 82h 16m total
  • Auckland to Chicago
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15/11-31/12
  • 15/11-31/12
  • 3 total stops
  • 52h 31m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($164 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($53 potential savings vs. average return price).
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Average for return flights in October 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

Sat 31/10

06:50-00:21

3 stops35h 31m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,082

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 16/11

20:20-17:00

1 stop39h 40m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,248
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 31/10

13:45-15:45

1 stop20h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,255

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 29/12

20:20-09:08

2 stops31h 48m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,266

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 25/12

13:20-23:12

2 stops28h 52m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,285

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 26/12

15:50-19:05

2 stops22h 15m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,285

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sun 27/12

19:00-11:28

1 stop35h 28m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,285

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 30/12

13:20-16:19

2 stops21h 59m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,387

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 10/11

08:00-00:21

3 stops35h 21m

Chicago O'Hare Intl

Wed 18/11

06:30-14:05

3 stops36h 35m

$2,101

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 10/11

13:20-09:05

2 stops38h 45m

Chicago O'Hare Intl

Wed 18/11

19:04-09:10

1 stop19h 06m

$2,307

Flights are sorted by cheapest return flights first.

Deals found on 30/9

Showing 1-10 of 18 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 25 hours 37 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 airline flying from Auckland to Chicago is Air New Zealand.

Air New Zealand
Air New Zealand
From $1,997

What are the cheapest airlines that fly to Chicago?

The cheapest airline flying from Auckland to Chicago is 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
670 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.4

Food

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed
Air New Zealand
8.0
Very Good
670 reviews
Air New Zealand
8.0
Very Good
670 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.4

Food

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed
Qantas Airways
7.5
Good
1,101 reviews
Air New Zealand
8.0
Very Good
670 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.4

Food

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed
United Airlines
7.4
Good
10,283 reviews
Air New Zealand
8.0
Very Good
670 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.4

Food

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

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, Air New Zealand 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 $307, while return flights cost around $314.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $316, however they can be found for as little as $314.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Christchurch offers the quickest one-way flight (22 hours 22 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

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

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