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$765+ Cheap flights to Chicago

— CHI
13 Nov — 20 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 26/1120:20 -
1 stop28h 54m
Thu 3/1207:00 -
2 stops27h 50m
Deal found 12/10$2,096
Sat 14/1108:00 -
2 stops25h 37m
Sat 28/1115:30 -
2 stops29h 35m
Deal found 11/10$2,194
Wed 4/1106:50 -
2 stops32h 09m
Sat 21/1115:30 -
2 stops34h 00m
Deal found 10/10$2,221
Wed 4/1119:55 -
1 stop22h 32m
Sat 21/1120:29 -
1 stop38h 16m
Deal found 10/10$2,239
Tue 10/1115:50 -
1 stop21h 59m
Tue 24/1115:00 -
1 stop19h 50m
Deal found 14/10$2,258
Tue 10/1116:05 -
1 stop22h 59m
Tue 24/1111:45 -
2 stops30h 55m
Deal found 13/10$2,282
Wed 23/1220:20 -
1 stop29h 07m
Wed 13/120:15 -
1 stop38h 30m
Deal found 11/10$2,289
Wed 25/1119:55 -
1 stop20h 50m
Wed 2/1212:55 -
1 stop21h 05m
Deal found 11/10$2,292
Fri 23/1014:25 -
1 stop41h 30m
Sun 8/1114:10 -
1 stop28h 15m
Deal found 13/10$2,321

Find flight deals to Chicago

Return from

$2,096

One-way from

$765

Popular in

October

Cheapest in

March

Average price

$3,555
26/11-3/12
  • 26/11-3/12
  • 3 total stops
  • 56h 44m total
  • Auckland to Chicago
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16/2-31/12
  • 16/2-31/12
  • 2 total stops
  • 35h 15m total
  • Auckland to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($336 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease ($93 potential savings vs. average return price).
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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

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 19/2

14:00-20:02

1 stop25h 02m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,074

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

06:50-14:32

2 stops26h 42m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,110

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

06:50-16:57

2 stops29h 07m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,249

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

14:45-22:20

2 stops26h 35m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,249

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 24/11

07:30-16:42

2 stops28h 12m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,249
Fastest return journey

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

$1,249

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 23/11

07:30-17:59

2 stops29h 29m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,249

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 26/11

20:20-00:53

2 stops23h 33m

Chicago O'Hare Intl

Thu 3/12

07:00-05:50

2 stops27h 50m

$2,151

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 4/11

06:50-19:59

2 stops32h 09m

Chicago O'Hare Intl

Sat 21/11

15:30-20:30

2 stops34h 00m

$2,221

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 4/11

19:55-23:27

1 stop22h 32m

Chicago O'Hare Intl

Sat 21/11

20:29-05:45

1 stop38h 16m

$2,239

Flights are sorted by cheapest return flights first.

Deals found on 12/10

Showing 1-10 of 18 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 20 hours 31 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 $1,984

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
674 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Food

7.4

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

Overall

8.0

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Food

7.4

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
1,110 reviews
Air New Zealand
8.0
Very Good
674 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Food

7.4

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
7.4
Good
10,364 reviews
Air New Zealand
8.0
Very Good
674 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.4

Boarding

8.2

Food

7.4

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 $308, 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 (20 hours 31 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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