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$842+ Cheap flights to Chicago

— CHI
23 Oct — 30 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

Mon 9/1115:50 -
1 stop38h 34m
Tue 10/1114:22 -
2 stops23h 48m
Deal found 21/9$1,667
Tue 3/1108:00 -
3 stops35h 21m
Sat 14/1106:30 -
3 stops46h 55m
Deal found 18/9$1,730
Thu 5/1107:30 -
2 stops28h 30m
Thu 12/1120:00 -
1 stop37h 55m
Deal found 20/9$1,807
Thu 5/1108:00 -
3 stops35h 21m
Thu 12/1106:30 -
3 stops40h 30m
Deal found 22/9$1,896
Mon 9/1114:50 -
3 stops28h 31m
Tue 10/1106:30 -
3 stops40h 25m
Deal found 21/9$1,899
Mon 2/1114:50 -
3 stops33h 23m
Mon 9/1110:26 -
3 stops32h 09m
Deal found 18/9$1,948

Find flight deals to Chicago

Return from

$1,667

One-way from

$842

Popular in

May

Cheapest in

November

Average price

$2,687
United Airlines
  • United Airlines
  • 9/11-10/11
  • 3 total stops
  • 62h 22m total
  • Auckland to Chicago
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3/11-31/12
  • 3/11-31/12
  • 3 total stops
  • 35h 21m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($231 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($54 potential savings vs. average return price).
Search Deals
Average for return flights in September 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

Tue 3/11

20:20-00:21

2 stops23h 01m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,021

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 31/10

14:50-09:56

3 stops37h 06m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,037
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 3/11

20:20-20:35

1 stop19h 15m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,051

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

15:50-23:26

2 stops26h 36m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,053

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 6/11

14:45-20:30

2 stops24h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,053

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 31/10

13:45-23:57

2 stops28h 12m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,053

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 6/11

15:05-09:35

3 stops37h 30m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,131

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 9/11

15:50-11:24

1 stop38h 34m

Chicago O'Hare Intl

Tue 10/11

14:22-09:10

2 stops23h 48m

$1,667

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

07:30-17:00

2 stops28h 30m

Chicago O'Hare Intl

Thu 12/11

20:00-04:55

1 stop37h 55m

$1,807

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 3/11

08:00-00:21

3 stops35h 21m

Chicago O'Hare Intl

Sat 14/11

06:30-05:00

2 stops27h 30m

$1,906

Flights are sorted by cheapest return flights first.

Deals found on 19/9

Showing 1-10 of 16 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

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 21 hours 7 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 and Qantas Airways.

Air New Zealand
Air New Zealand
From $1,650
Qantas Airways
Qantas Airways
From $1,441

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Qantas Airways 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
669 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.5

Entertainment

7.4

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

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.5

Entertainment

7.4

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
669 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.5

Entertainment

7.4

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
10,230 reviews
Air New Zealand
8.0
Very Good
669 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.5

Entertainment

7.4

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 Canada
7.1
Good
11,668 reviews
Air New Zealand
8.0
Very Good
669 reviews
Check prices

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.5

Entertainment

7.4

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, 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 $301, while return flights cost around $308.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $310, however they can be found for as little as $308.

  • 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 7 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

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

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