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$875+ Cheap flights to Chicago

— CHI
16 Oct — 23 Oct1
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

Wed 21/1020:15 -
1 stop28h 19m
Sat 24/1020:01 -
1 stop39h 49m
Deal found 15/9$1,876
Tue 3/1113:20 -
1 stop18h 04m
Fri 25/1206:00 -
1 stop32h 55m
Deal found 16/9$1,923
Tue 3/1113:20 -
1 stop19h 52m
Thu 24/1206:00 -
1 stop32h 55m
Deal found 16/9$1,937
Sat 31/1019:00 -
1 stop19h 37m
Sat 7/1121:57 -
1 stop36h 48m
Deal found 15/9$1,995
Sat 31/1014:50 -
2 stops20h 15m
Sat 7/1121:35 -
1 stop37h 10m
Deal found 16/9$2,113
Thu 12/1114:50 -
3 stops33h 23m
Sun 22/1106:40 -
3 stops46h 35m
Deal found 14/9$2,129
Fri 6/1119:50 -
1 stop19h 09m
Fri 25/1219:34 -
2 stops51h 21m
Deal found 16/9$2,149
Mon 2/1119:50 -
1 stop19h 09m
Fri 25/1219:34 -
2 stops51h 21m
Deal found 16/9$2,172
Mon 2/1114:55 -
1 stop40h 35m
Sun 15/1114:10 -
1 stop28h 15m
Deal found 14/9$2,193
Sat 31/1006:50 -
3 stops35h 31m
Sat 7/1114:11 -
3 stops44h 39m
Deal found 16/9$2,200
Thu 12/1114:55 -
1 stop40h 35m
Sun 22/1114:10 -
1 stop28h 15m
Deal found 14/9$2,205

Find flight deals to Chicago

Return from

$1,876

One-way from

$875

Popular in

May

Cheapest in

November

Average price

$2,679
21/10-24/10
  • 21/10-24/10
  • 2 total stops
  • 68h 08m total
  • Auckland to Chicago
Search Deals
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. 10% potential increase in price ($248 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($56 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 21/10

15:00-06:34

2 stops33h 34m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$875

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 23/2

14:50-07:05

2 stops35h 15m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$969

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 2/2

19:55-13:04

1 stop36h 09m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,056

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Fri 29/1

15:50-05:01

1 stop32h 11m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,086

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Tue 3/11

20:20-00:21

2 stops47h 01m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,096
Fastest return journey

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

$1,237

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

14:45-21:53

2 stops26h 08m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,253

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

06:50-16:16

2 stops28h 26m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,257

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Sat 14/11

14:45-20:55

1 stop25h 10m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,260

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 2/11

20:20-22:46

2 stops21h 26m

Chicago O'Hare Intl

Thu 24/12

06:00-05:50

1 stop28h 50m

$2,275

Flights are sorted by cheapest return flights first.

Deals found on 15/9

Showing 1-10 of 19 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 21 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, Qantas Airways and American Airlines.

Air New Zealand
Air New Zealand
From $1,788
Qantas Airways
Qantas Airways
From $1,436
American Airlines
American Airlines
From $1,928

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Qantas Airways, Air New Zealand and American Airlines.

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
669 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.5

Overall

8.0

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

Food

7.5

Boarding

8.2

Crew

8.5

Overall

8.0

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
1,099 reviews
Air New Zealand
8.0
Very Good
669 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.5

Overall

8.0

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
7.4
Good
10,214 reviews
Air New Zealand
8.0
Very Good
669 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.5

Overall

8.0

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 Canada
7.1
Good
11,639 reviews
Air New Zealand
8.0
Very Good
669 reviews
Check prices

Food

7.5

Boarding

8.2

Crew

8.5

Overall

8.0

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, 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 $301, while return flights cost around $307.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $309, however they can be found for as little as $307.

  • 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 (21 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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