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$897+ Cheap flights to Chicago

— CHI
6 Oct — 13 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

Thu 5/1107:30 -
2 stops27h 35m
Mon 9/1120:00 -
2 stops66h 10m
Deal found 2/9$2,166
Fri 16/1019:50 -
1 stop36h 35m
Fri 23/1020:01 -
2 stops48h 04m
Deal found 1/9$2,174
Mon 19/1020:15 -
1 stop27h 30m
Mon 26/1005:59 -
1 stop29h 51m
Deal found 4/9$2,254
Sat 17/1020:15 -
1 stop28h 19m
Sat 24/1020:01 -
2 stops48h 44m
Deal found 2/9$2,266
Sat 17/1014:50 -
1 stop38h 35m
Sat 24/1022:15 -
1 stop37h 30m
Deal found 2/9$2,318
Fri 16/1013:25 -
2 stops28h 05m
Fri 23/1021:42 -
2 stops41h 28m
Deal found 6/9$2,322
Thu 5/1120:20 -
1 stop20h 40m
Mon 9/1118:20 -
1 stop19h 50m
Deal found 2/9$2,344

Find flight deals to Chicago

Return from

$2,166

One-way from

$823

Popular in

May

Cheapest in

November

Average price

$2,616
American Airlines
  • American Airlines
  • 5/11-9/11
  • 4 total stops
  • 93h 45m 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. 8% potential increase in price ($215 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($52 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

Thu 11/2

16:05-20:00

2 stops22h 55m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,144

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 2/11

19:00-22:00

1 stop22h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,192
Fastest return journey

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 17/2

19:55-21:38

1 stop20h 43m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,226

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Mon 1/3

19:00-23:02

1 stop23h 02m

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

Wed 17/2

14:45-21:53

2 stops26h 08m

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

Wed 17/2

06:00-18:35

2 stops31h 35m

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

Mon 14/9

06:00-00:30

2 stops35h 30m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,246

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Thu 24/12

15:50-05:56

1 stop33h 06m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,248

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

$1,248

AucklandChicago

AKL Auckland Intl - ORD Chicago O'Hare Intl

AKLORD

Auckland Intl

Wed 23/12

15:50-22:29

1 stop25h 39m

Chicago O'Hare Intl

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,248

Flights are sorted by cheapest return flights first.

Deals found on 6/9

Showing 1-10 of 15 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 19 hours 46 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 $1,746
Qantas Airways
Qantas Airways
From $1,403
American Airlines
American Airlines
From $1,497

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Qantas Airways, American Airlines and 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
668 reviews
Check prices

Comfort

7.9

Crew

8.5

Food

7.4

Overall

8.0

Entertainment

7.4

Boarding

8.2

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

Comfort

7.9

Crew

8.5

Food

7.4

Overall

8.0

Entertainment

7.4

Boarding

8.2

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
1,090 reviews
Air New Zealand
8.0
Very Good
668 reviews
Check prices

Comfort

7.9

Crew

8.5

Food

7.4

Overall

8.0

Entertainment

7.4

Boarding

8.2

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
10,173 reviews
Air New Zealand
8.0
Very Good
668 reviews
Check prices

Comfort

7.9

Crew

8.5

Food

7.4

Overall

8.0

Entertainment

7.4

Boarding

8.2

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
11,595 reviews
Air New Zealand
8.0
Very Good
668 reviews
Check prices

Comfort

7.9

Crew

8.5

Food

7.4

Overall

8.0

Entertainment

7.4

Boarding

8.2

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 $294, while return flights cost around $299.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $301, however they can be found for as little as $299.

  • 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 (19 hours 46 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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