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$896+ Cheap flights to Chicago

— CHI
28 Oct — 4 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

Thu 5/1106:00 -
2 stops43h 05m
Mon 9/1121:06 -
2 stops65h 04m
Deal found 24/9$1,592
Sat 7/1116:55 -
1 stop38h 40m
Sat 14/1116:43 -
2 stops45h 27m
Deal found 23/9$1,772
Mon 2/1114:50 -
3 stops33h 23m
Mon 9/1106:30 -
3 stops36h 05m
Deal found 27/9$1,821
Mon 9/1114:50 -
3 stops33h 23m
Mon 16/1110:26 -
3 stops42h 49m
Deal found 25/9$1,837
Wed 11/1108:00 -
3 stops35h 21m
Wed 18/1106:30 -
3 stops40h 30m
Deal found 27/9$1,895
Tue 15/1213:20 -
1 stop25h 40m
Tue 5/108:10 -
1 stop30h 45m
Deal found 25/9$1,908
Tue 10/1108:00 -
3 stops35h 21m
Wed 18/1106:30 -
3 stops40h 30m
Deal found 27/9$1,950
Tue 10/1120:20 -
1 stop19h 15m
Wed 18/1106:00 -
1 stop28h 50m
Deal found 27/9$1,962
Mon 9/1120:20 -
1 stop28h 38m
Mon 16/1110:25 -
1 stop24h 25m
Deal found 25/9$1,964

Find flight deals to Chicago

Return from

$1,592

One-way from

$896

Popular in

May

Cheapest in

November

Average price

$2,716
American Airlines
  • American Airlines
  • 5/11-9/11
  • 4 total stops
  • 108h 09m total
  • Auckland to Chicago
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21/10-31/12
  • 21/10-31/12
  • 2 total stops
  • 33h 34m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($199 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($52 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

Wed 17/2

14:45-17:21

1 stop21h 36m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,054

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 2/11

06:50-17:00

2 stops29h 10m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,055

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

15:50-18:38

1 stop21h 48m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,064

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 21/11

09:25-20:25

2 stops30h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,085
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 21/12

15:50-16:59

1 stop20h 09m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,091

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 23/12

06:00-23:05

2 stops36h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,108

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 5/11

06:00-06:05

2 stops43h 05m

Chicago O'Hare Intl

Mon 9/11

20:00-09:10

2 stops66h 10m

$1,624

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 10/11

14:45-13:37

1 stop17h 52m

Chicago O'Hare Intl

Tue 17/11

07:30-08:55

2 stops30h 25m

$2,077

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 30/10

13:45-17:50

1 stop22h 05m

Chicago O'Hare Intl

Sun 8/11

18:59-08:55

1 stop18h 56m

$2,077

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sun 1/11

14:45-17:40

2 stops20h 55m

Chicago O'Hare Intl

Sat 7/11

15:30-08:55

2 stops22h 25m

$2,077

Flights are sorted by cheapest return flights first.

Deals found on 27/9

Showing 1-10 of 14 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 20 hours 45 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 $1,813
Qantas Airways
Qantas Airways
From $1,457

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
670 reviews
Check prices

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Crew

8.5

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

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Crew

8.5

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
1,102 reviews
Air New Zealand
8.0
Very Good
670 reviews
Check prices

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Crew

8.5

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
10,246 reviews
Air New Zealand
8.0
Very Good
670 reviews
Check prices

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Crew

8.5

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, 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 $305, while return flights cost around $311.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $313, however they can be found for as little as $311.

  • 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 (20 hours 45 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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