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$1,045+ Cheap flights to Chicago

— CHI
22 Nov — 29 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 7/1214:00 -
1 stop19h 37m
Mon 14/1215:00 -
2 stops25h 00m
Deal found 22/10$2,110
Thu 10/1215:50 -
1 stop32h 12m
Fri 25/1213:44 -
1 stop24h 26m
Deal found 21/10$2,161
Tue 17/1106:20 -
2 stops32h 39m
Tue 24/1112:50 -
3 stops32h 15m
Deal found 20/10$2,195
Thu 10/1213:20 -
2 stops25h 43m
Fri 25/1221:05 -
1 stop41h 50m
Deal found 21/10$2,267
Sun 13/1215:50 -
1 stop22h 15m
Mon 28/1205:30 -
1 stop29h 15m
Deal found 19/10$2,290
Wed 18/1120:20 -
2 stops32h 07m
Wed 25/1122:00 -
1 stop36h 50m
Deal found 21/10$2,295
Tue 10/1115:50 -
1 stop24h 55m
Wed 18/1107:35 -
1 stop30h 35m
Deal found 18/10$2,316
Mon 2/1114:55 -
1 stop40h 35m
Sun 8/1114:10 -
1 stop28h 15m
Deal found 22/10$2,320
Tue 10/1116:05 -
1 stop22h 59m
Wed 18/1113:24 -
2 stops29h 41m
Deal found 18/10$2,321
Sun 1/1115:50 -
2 stops35h 06m
Wed 4/1107:35 -
1 stop30h 35m
Deal found 18/10$2,362

Find flight deals to Chicago

Return from

$2,110

One-way from

$1,045

Popular in

October

Cheapest in

March

Average price

$3,505
Air Canada
  • Air Canada
  • 7/12-14/12
  • 3 total stops
  • 44h 37m total
  • Auckland to Chicago
Search Deals
23/11-31/12
  • 23/11-31/12
  • 2 total stops
  • 34h 24m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($331 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
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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
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 17/12

13:20-14:12

1 stop19h 52m

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

Tue 24/11

15:50-22:29

1 stop25h 39m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,219

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 2/12

06:40-18:30

2 stops30h 50m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,235

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 27/10

13:45-20:38

2 stops24h 53m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,242

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 17/12

15:50-20:00

2 stops23h 10m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,243

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

14:45-20:17

2 stops24h 32m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,243

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 28/12

15:50-19:30

2 stops22h 40m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,247

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

14:45-18:05

2 stops22h 20m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,247

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

15:50-23:59

2 stops27h 09m

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

06:00-16:42

2 stops29h 42m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,256

Flights are sorted by cheapest return flights first.

Deals found on 18/10

Showing 1-10 of 21 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 27 hours 21 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 $1,956

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
675 reviews
Check prices

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.4

Comfort

7.9

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

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.4

Comfort

7.9

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
1,116 reviews
Air New Zealand
8.0
Very Good
675 reviews
Check prices

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.4

Comfort

7.9

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
7.3
Good
10,423 reviews
Air New Zealand
8.0
Very Good
675 reviews
Check prices

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.4

Comfort

7.9

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, 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 $304, while return flights cost around $310.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $312, however they can be found for as little as $310.

  • 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 (24 hours 54 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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