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 Canada is rated the highest out of the airlines that fly to Chicago.

What is the cheapest airport to fly to in Chicago?

Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost $161, while return flights cost around $145.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around $105, however they can be found for as little as $87.

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 (25 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).

$943+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	$1,988
One-way from	$960
Popular in	April
Cheapest in	February
Average price	$2,208

17/7-31/7
4 total stops
74h 05m total
Auckland to Chicago

Search Deals

12/8
2 total stops
25h 19m total
Auckland to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price ($164 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($68 potential savings vs. average return price).

Search Deals

Average for return flights in June 2025

Search Deals

Find flight deals to Chicago

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 June 2025.

Fri 26/915:50AKL - ORD

1 stop37h 25mAmerican Airlines

Sat 25/1019:03ORD - AKL

1 stop20h 22mAmerican Airlines

Deal found 13/6$1,884

Thu 25/913:25AKL - ORD

1 stop42h 00mCathay Pacific

Sat 25/1016:00ORD - AKL

1 stop47h 40mCathay Pacific

Deal found 14/6$1,922

Thu 17/715:55AKL - ORD

2 stops39h 30mMultiple Airlines

Thu 31/716:00ORD - AKL

2 stops34h 35mMultiple Airlines

Deal found 12/6$1,988

Thu 25/906:35AKL - ORD

2 stops27h 07mAir Canada

Sat 25/1008:51ORD - AKL

2 stops37h 59mAir Canada

Deal found 14/6$2,018

Mon 11/806:10AKL - ORD

2 stops26h 45mQantas Airways

Tue 9/918:47ORD - AKL

2 stops26h 18mQantas Airways

Deal found 13/6$2,103

Thu 17/719:40AKL - ORD

1 stop21h 35mAir New Zealand

Thu 31/721:07ORD - AKL

1 stop39h 23mAir New Zealand

Deal found 12/6$2,447

Mon 28/713:50AKL - ORD

2 stops20h 15mUnited Airlines

Mon 4/821:07ORD - AKL

1 stop39h 23mUnited Airlines

Deal found 13/6$2,468

Mon 14/706:35AKL - ORD

2 stops55h 35mEVA Air

Sun 27/700:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 13/6$3,674

Tue 15/706:00AKL - ORD

2 stops50h 45mEmirates

Fri 1/820:35ORD - AKL

2 stops48h 10mEmirates

Deal found 13/6$3,749

Sun 13/723:55AKL - ORD

3 stops63h 33mSingapore Airlines

Sat 26/712:20ORD - AKL

3 stops55h 00mSingapore Airlines

Deal found 13/6$5,413

Best flights to Chicago
Discover carefully curated flight deals to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 14 June 2025.

Thu 17/715:55AKL - ORD

2 stops39h 30mMultiple Airlines

Thu 31/716:00ORD - AKL

2 stops34h 35mMultiple Airlines

Deal found 12/6$1,988

Sat 12/714:55AKL - ORD

2 stops32h 10mAmerican Airlines

Wed 23/705:00ORD - AKL

2 stops36h 25mAmerican Airlines

Deal found 13/6$2,040

Mon 14/713:25AKL - ORD

1 stop42h 00mCathay Pacific

Mon 28/716:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 13/6$2,041

Mon 11/806:10AKL - ORD

2 stops26h 45mQantas Airways

Tue 9/918:47ORD - AKL

2 stops26h 18mQantas Airways

Deal found 13/6$2,103

Thu 17/719:40AKL - ORD

1 stop21h 35mAir New Zealand

Thu 31/721:07ORD - AKL

1 stop39h 23mAir New Zealand

Deal found 12/6$2,447

Mon 28/713:50AKL - ORD

2 stops20h 15mUnited Airlines

Mon 4/821:07ORD - AKL

1 stop39h 23mUnited Airlines

Deal found 13/6$2,468

Mon 11/819:55AKL - ORD

3 stops43h 10mAir Canada

Wed 27/815:40ORD - AKL

2 stops32h 10mAir Canada

Deal found 12/6$2,850

Mon 14/706:35AKL - ORD

2 stops55h 35mEVA Air

Sun 27/700:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 13/6$3,674

Tue 15/707:30AKL - ORD

2 stops49h 15mEmirates

Sun 27/720:35ORD - AKL

2 stops58h 20mEmirates

Deal found 13/6$3,749

Sun 13/723:55AKL - ORD

3 stops63h 33mSingapore Airlines

Sat 26/712:20ORD - AKL

3 stops55h 00mSingapore Airlines

Deal found 13/6$5,413

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 14 June 2025 and is based on user searches.

Tue 17/606:10AKL - ORD

2 stops31h 44mQantas Airways

Sat 12/718:45ORD - AKL

2 stops26h 20mQantas Airways

Deal found 13/6$2,208

Tue 1/715:50AKL - ORD

2 stops31h 20mAmerican Airlines

Sun 20/707:22ORD - AKL

2 stops34h 03mAmerican Airlines

Deal found 14/6$2,000

Sun 13/723:55AKL - ORD

3 stops63h 33mSingapore Airlines

Sat 26/712:20ORD - AKL

3 stops55h 00mSingapore Airlines

Deal found 13/6$5,413

Mon 14/713:25AKL - ORD

1 stop42h 00mCathay Pacific

Mon 28/716:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 13/6$2,041

Mon 14/719:55AKL - ORD

3 stops43h 10mAir Canada

Tue 29/715:40ORD - AKL

2 stops30h 15mAir Canada

Deal found 13/6$3,551

Mon 14/706:35AKL - ORD

2 stops55h 35mEVA Air

Sun 27/700:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 13/6$3,674

Tue 15/707:30AKL - ORD

2 stops49h 15mEmirates

Sun 27/720:35ORD - AKL

2 stops58h 20mEmirates

Deal found 13/6$3,749

Thu 17/715:55AKL - ORD

2 stops39h 30mMultiple Airlines

Thu 31/716:00ORD - AKL

2 stops34h 35mMultiple Airlines

Deal found 12/6$1,988

Thu 17/719:40AKL - ORD

1 stop21h 35mAir New Zealand

Thu 31/721:07ORD - AKL

1 stop39h 23mAir New Zealand

Deal found 12/6$2,447

Mon 28/713:50AKL - ORD

2 stops20h 15mUnited Airlines

Mon 4/821:07ORD - AKL

1 stop39h 23mUnited Airlines

Deal found 13/6$2,468

One-way flights to Chicago
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 14 June 2025.

Tue 12/806:35AKL - ORD

2 stops25h 19mMultiple Airlines

Deal found 13/6$960

Tue 12/806:35AKL - ORD

2 stops40h 03mAir Canada

Deal found 14/6$962

Tue 5/806:00AKL - ORD

2 stops25h 17mQantas Airways

Deal found 13/6$1,061

Fri 1/815:50AKL - ORD

1 stop32h 12mAmerican Airlines

Deal found 12/6$1,093

Sun 27/720:15AKL - ORD

3 stops36h 42mUnited Airlines

Deal found 12/6$1,424

Wed 18/613:25AKL - ORD

1 stop42h 00mCathay Pacific

Deal found 13/6$1,696

Sat 28/621:00AKL - ORD

2 stops41h 41mChina Eastern

Deal found 12/6$5,923

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

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 26/9

15:50-12:15

1 stop37h 25m

Chicago O'Hare Intl

Sat 25/10

19:03-09:25

1 stop20h 22m

$1,884

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 25/9

13:25-14:25

1 stop42h 00m

Chicago O'Hare Intl

Sat 25/10

16:00-09:40

1 stop47h 40m

$1,922

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 17/7

15:55-14:25

2 stops39h 30m

Chicago O'Hare Intl

Thu 31/7

16:00-19:35

2 stops34h 35m

$1,988

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 25/9

06:35-16:42

2 stops27h 07m

Chicago O'Hare Intl

Sat 25/10

08:51-16:50

2 stops37h 59m

$2,018

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 11/8

06:10-15:55

2 stops26h 45m

Chicago O'Hare Intl

Tue 9/9

18:47-14:05

2 stops26h 18m

$2,103

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 17/7

19:40-00:15

1 stop21h 35m

Chicago O'Hare Intl

Thu 31/7

21:07-05:30

1 stop39h 23m

$2,447

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 28/7

13:50-17:05

2 stops20h 15m

Chicago O'Hare Intl

Mon 4/8

21:07-05:30

1 stop39h 23m

$2,468

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 14/7

06:35-21:10

2 stops55h 35m

Chicago O'Hare Intl

Sun 27/7

00:30-09:15

1 stop39h 45m

$3,674

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 15/7

06:00-15:45

2 stops50h 45m

Chicago O'Hare Intl

Fri 1/8

20:35-13:45

2 stops48h 10m

$3,749

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 13/7

23:55-22:28

3 stops63h 33m

Chicago O'Hare Intl

Sat 26/7

12:20-12:20

3 stops55h 00m

$5,413

Flights are sorted by cheapest return flights first.

Deals found on 13/6

Showing 1-10 of 20 results

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

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

The best time to book flights to Chicago is 88 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

How long is the flight to Chicago?

On average, a flight from Auckland to Chicago takes 25 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.

When is the cheapest time to fly to Chicago?

Users looking for the lowest fares to Chicago should consider flying on Saturday afternoons, when prices are typically cheapest. Budget-minded travellers will want to avoid Saturday evenings, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Auckland to Chicago are Qantas Airways, United Airlines and Air New Zealand.

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Auckland to Chicago are Air Canada, Qantas Airways and United 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

EVA Air

8.4

Very Good

1,204 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

EVA Air

8.4

Very Good

1,204 reviews

EVA Air

8.4

Very Good

1,204 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

Emirates

8.1

Very Good

3,266 reviews

EVA Air

8.4

Very Good

1,204 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

Singapore Airlines

8.1

Very Good

1,304 reviews

EVA Air

8.4

Very Good

1,204 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

Air New Zealand

8.0

Very Good

483 reviews

EVA Air

8.4

Very Good

1,204 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

Cathay Pacific

7.6

Good

892 reviews

EVA Air

8.4

Very Good

1,204 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

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 Canada is rated the highest out of the airlines that fly to Chicago.
What is the cheapest airport to fly to in Chicago?
Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost $161, while return flights cost around $145.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around $105, however they can be found for as little as $87.
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 (25 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

Popular United States flight routes

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Flights from Auckland to George Bush Intcntl

Flights from Auckland to John F Kennedy Intl

Flights from Los Angeles to Las Vegas

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Flights from Los Angeles to Seattle

Fly with Cheapflights

How does Cheapflights help users find flights to Chicago?

When you search for this flight to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

Why should you use Cheapflights to find cheap flight tickets to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights to Chicago with no change fees?

Yes, we can. To see specific flights to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alerts, which notifies users when flight prices change. Track prices for your flight to Chicago today and book when you’re ready!

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$943+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/11. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 134,765 searches and data was last updated on 14 June 2025.

Return from

One-way from

Popular in

Cheapest in

Average price

Find flight deals to Chicago

Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 June 2025.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 June 2025.

Cheapflights Fare Finder

Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 134,765 searches and data was last updated on 14 June 2025.

Use the filters below to find and compare flights to Chicago that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight to Chicago

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight from Auckland to Chicago. Price data was last updated on 9 June 2025.

How long is the flight to Chicago?

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly return from Auckland to Chicago. Price data was last updated on 1 September 2024.

What are the most popular airlines that fly to Chicago?

What are the cheapest airlines that fly to Chicago?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

FAQs about flying to Chicago

Can I find cheaper flights to Chicago if I am willing to have stopovers?

What is the best airline to fly to Chicago?

What is the cheapest airport to fly to in Chicago?

How much is a return flight to Chicago?

Where does the fastest flight to Chicago depart from?

Does Chicago O'Hare Intl have rental cars?

Are there hotels close to Chicago O'Hare Intl?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Airports serving Chicago

Book a flight to or from one of these Chicago airports.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights to Chicago?

Why should you use Cheapflights to find cheap flight tickets to Chicago?

Can Cheapflights find flights to Chicago with no change fees?

Can Cheapflights notify me if prices for flights to Chicago become cheaper?

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Travel Smart

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 June 2025.