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$890+ Cheap flights to Chicago

— CHI
10 Dec — 17 Dec1
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 7/1219:00 -
1 stop18h 56m
Wed 9/1210:25 -
1 stop23h 35m
Deal found 8/11$2,242
Mon 7/1207:30 -
3 stops40h 31m
Wed 9/1207:25 -
3 stops35h 40m
Deal found 8/11$2,260
Mon 7/1214:00 -
1 stop19h 37m
Wed 9/1215:47 -
2 stops24h 13m
Deal found 8/11$2,285
Thu 24/1215:50 -
1 stop22h 11m
Thu 31/1217:45 -
1 stop41h 05m
Deal found 9/11$2,304
Sun 20/1215:50 -
1 stop32h 11m
Mon 4/118:20 -
1 stop19h 50m
Deal found 8/11$2,308
Thu 24/1215:50 -
1 stop26h 43m
Tue 29/1207:00 -
1 stop27h 45m
Deal found 8/11$2,365
Wed 23/1215:50 -
1 stop26h 43m
Wed 30/1221:43 -
1 stop37h 02m
Deal found 7/11$2,388
Wed 23/1214:00 -
1 stop19h 37m
Wed 30/1213:55 -
2 stops26h 05m
Deal found 7/11$2,408
Wed 23/1215:50 -
2 stops25h 11m
Wed 30/1218:14 -
1 stop19h 56m
Deal found 8/11$2,441
Thu 24/1215:50 -
2 stops22h 15m
Thu 31/1216:35 -
1 stop21h 35m
Deal found 9/11$2,470

Find flight deals to Chicago

Return from

$1,780

One-way from

$890

Popular in

October

Cheapest in

April

Average price

$2,347
American Airlines
  • American Airlines
  • 4/2-8/2
  • 2 total stops
  • 52h 28m total
  • Auckland to Chicago
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19/2-31/12
  • 19/2-31/12
  • 2 total stops
  • 35h 15m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($329 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($92 potential savings vs. average return price).
Search Deals
Average for return flights in November 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

Fri 19/2

14:50-00:26

3 stops52h 36m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$938

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

14:00-14:32

1 stop19h 32m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,150

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

15:50-22:29

1 stop25h 39m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,227

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

14:45-16:41

2 stops20h 56m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,236
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

14:45-13:37

1 stop17h 52m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,236

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 15/12

15:50-19:54

2 stops23h 04m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,238

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 16/1

14:45-22:08

2 stops26h 23m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,238

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

06:00-22:31

2 stops35h 31m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,239

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 4/2

13:20-15:52

2 stops21h 32m

Chicago O'Hare Intl

Mon 8/2

08:15-09:55

1 stop30h 40m

$1,782

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 4/2

15:50-17:05

2 stops20h 15m

Chicago O'Hare Intl

Mon 8/2

15:43-09:10

2 stops22h 27m

$2,441

Flights are sorted by cheapest return flights first.

Deals found on 7/11

Showing 1-10 of 14 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 18 hours 56 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 $1,983
Qantas Airways
Qantas Airways
From $1,757

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
683 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.5

Overall

8.0

Food

7.5

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

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.5

Overall

8.0

Food

7.5

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
1,123 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.5

Overall

8.0

Food

7.5

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
7.3
Good
10,471 reviews
Air New Zealand
8.0
Very Good
683 reviews
Check prices

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.5

Overall

8.0

Food

7.5

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 $208, 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, Auckland Intl offers the quickest one-way flight (18 hours 56 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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