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$1,044+ Cheap flights to Chicago

— CHI
29 Nov — 6 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

Fri 25/1215:50 -
1 stop32h 54m
Thu 28/113:44 -
1 stop24h 26m
Deal found 25/10$1,928
Wed 9/1214:00 -
1 stop19h 37m
Fri 25/1215:30 -
1 stop24h 30m
Deal found 29/10$2,194
Fri 25/1214:50 -
3 stops33h 59m
Thu 28/106:21 -
3 stops46h 54m
Deal found 25/10$2,241
Thu 29/1014:50 -
2 stops35h 06m
Wed 4/1121:57 -
1 stop40h 13m
Deal found 26/10$2,294
Mon 2/1114:55 -
1 stop40h 35m
Sun 15/1114:10 -
1 stop28h 15m
Deal found 27/10$2,308
Tue 3/1116:05 -
2 stops22h 59m
Tue 10/1110:32 -
2 stops32h 08m
Deal found 25/10$2,369
Tue 3/1119:50 -
1 stop19h 05m
Tue 10/1112:42 -
1 stop25h 28m
Deal found 27/10$2,379
Mon 2/1114:55 -
1 stop40h 35m
Sun 15/1106:44 -
2 stops35h 41m
Deal found 27/10$2,388
Thu 10/1215:50 -
1 stop22h 15m
Thu 24/1205:30 -
1 stop29h 15m
Deal found 29/10$2,404

Find flight deals to Chicago

Return from

$1,928

One-way from

$891

Popular in

October

Cheapest in

April

Average price

$3,544
Qantas Airways
  • Qantas Airways
  • 25/12-28/1
  • 2 total stops
  • 57h 20m total
  • Auckland to Chicago
Search Deals
1/3-31/12
  • 1/3-31/12
  • 2 total stops
  • 35h 15m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($323 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($91 potential savings vs. average return price).
Search Deals
Average for return flights in October 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

Tue 24/11

07:30-06:14

2 stops41h 44m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,190

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

14:45-23:54

2 stops28h 09m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,247
Fastest return journey

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

$1,250

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

06:10-15:24

2 stops28h 14m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,261

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

07:30-17:11

2 stops28h 41m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,261

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

15:50-18:38

2 stops21h 48m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,279

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 29/12

14:45-00:02

2 stops28h 17m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,327

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

16:20-21:45

3 stops48h 25m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$2,052

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 9/12

14:00-14:37

1 stop19h 37m

Chicago O'Hare Intl

Fri 25/12

15:45-11:00

2 stops24h 15m

$2,258

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 3/11

14:55-12:30

1 stop40h 35m

Chicago O'Hare Intl

Tue 10/11

14:10-00:25

2 stops39h 15m

$2,413

Flights are sorted by cheapest return flights first.

Deals found on 29/10

Showing 1-10 of 17 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 22 hours 15 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 $1,977

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
679 reviews
Check prices

Boarding

8.2

Entertainment

7.4

Overall

8.0

Food

7.4

Comfort

7.9

Crew

8.5

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

Boarding

8.2

Entertainment

7.4

Overall

8.0

Food

7.4

Comfort

7.9

Crew

8.5

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
1,121 reviews
Air New Zealand
8.0
Very Good
679 reviews
Check prices

Boarding

8.2

Entertainment

7.4

Overall

8.0

Food

7.4

Comfort

7.9

Crew

8.5

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
10,451 reviews
Air New Zealand
8.0
Very Good
679 reviews
Check prices

Boarding

8.2

Entertainment

7.4

Overall

8.0

Food

7.4

Comfort

7.9

Crew

8.5

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 $307, while return flights cost around $313.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $315, however they can be found for as little as $313.

  • 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 15 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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