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 $160, while return flights cost around $144.

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 (22 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).

$771+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	$1,436
One-way from	$771
Popular in	April
Cheapest in	February
Average price	$2,202

American Airlines
25/9-25/10
2 total stops
59h 33m total
Auckland to Chicago

Search Deals

Air Canada
18/9
2 total stops
27h 07m total
Auckland to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price ($155 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 30 June 2025.

Thu 25/915:50AKL - ORD

1 stop37h 25mAmerican Airlines

Sat 25/1017:17ORD - AKL

1 stop22h 08mAmerican Airlines

Deal found 30/6$1,436

Thu 25/906:35AKL - ORD

2 stops27h 07mAir Canada

Sat 25/1015:40ORD - AKL

2 stops31h 10mAir Canada

Deal found 30/6$1,527

Wed 13/813:55AKL - ORD

2 stops32h 45mMultiple Airlines

Wed 20/807:05ORD - AKL

2 stops36h 35mMultiple Airlines

Deal found 28/6$1,529

Mon 14/713:50AKL - ORD

2 stops20h 15mUnited Airlines

Tue 29/716:20ORD - AKL

2 stops21h 50mUnited Airlines

Deal found 29/6$1,954

Wed 29/1020:10AKL - ORD

1 stop18h 15mAir New Zealand

Tue 11/1113:00ORD - AKL

1 stop21h 00mAir New Zealand

Deal found 28/6$1,956

Mon 11/806:00AKL - ORD

2 stops28h 08mQantas Airways

Tue 9/918:47ORD - AKL

2 stops26h 18mQantas Airways

Deal found 30/6$2,096

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 30 June 2025.

Thu 25/915:50AKL - ORD

1 stop37h 25mAmerican Airlines

Sat 25/1017:17ORD - AKL

1 stop22h 08mAmerican Airlines

Deal found 30/6$1,436

Thu 25/906:35AKL - ORD

2 stops27h 07mAir Canada

Sat 25/1015:40ORD - AKL

2 stops31h 10mAir Canada

Deal found 30/6$1,527

Wed 13/813:55AKL - ORD

2 stops32h 45mMultiple Airlines

Wed 20/807:05ORD - AKL

2 stops36h 35mMultiple Airlines

Deal found 28/6$1,529

Mon 14/713:50AKL - ORD

2 stops20h 15mUnited Airlines

Tue 29/716:20ORD - AKL

2 stops21h 50mUnited Airlines

Deal found 29/6$1,954

Fri 26/920:15AKL - ORD

1 stop20h 00mAir New Zealand

Fri 10/1007:10ORD - AKL

1 stop28h 20mAir New Zealand

Deal found 28/6$2,037

Mon 11/806:00AKL - ORD

2 stops28h 08mQantas Airways

Tue 9/918:47ORD - AKL

2 stops26h 18mQantas Airways

Deal found 30/6$2,096

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 30 June 2025 and is based on user searches.

Tue 1/713:25AKL - ORD

1 stop42h 00mMultiple Airlines

Sun 20/716:00ORD - AKL

2 stops39h 10mMultiple Airlines

Deal found 29/6$2,729

Tue 1/713:25AKL - ORD

2 stops27h 10mQantas Airways

Sun 20/719:03ORD - AKL

2 stops26h 02mQantas Airways

Deal found 29/6$2,918

Tue 1/713:25AKL - ORD

1 stop42h 00mCathay Pacific

Sun 20/716:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 29/6$3,476

Tue 1/709:40AKL - ORD

1 stop28h 30mEVA Air

Sun 20/700:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 29/6$4,533

Mon 14/716:25AKL - ORD

1 stop31h 58mAmerican Airlines

Tue 29/719:03ORD - AKL

2 stops26h 02mAmerican Airlines

Deal found 29/6$1,641

Mon 14/713:50AKL - ORD

2 stops20h 15mUnited Airlines

Tue 29/716:20ORD - AKL

2 stops21h 50mUnited Airlines

Deal found 29/6$1,954

Mon 14/723:55AKL - ORD

2 stops34h 04mSingapore Airlines

Tue 29/712:06ORD - AKL

3 stops41h 04mSingapore Airlines

Deal found 29/6$6,939

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 30 June 2025.

Thu 18/906:35AKL - ORD

2 stops27h 07mAir Canada

Deal found 28/6$771

Tue 12/806:00AKL - ORD

2 stops25h 54mMultiple Airlines

Deal found 29/6$791

Thu 18/913:50AKL - ORD

1 stop18h 13mUnited Airlines

Deal found 28/6$1,018

Wed 13/806:45AKL - ORD

2 stops29h 27mQantas Airways

Deal found 29/6$1,032

Fri 1/815:50AKL - ORD

1 stop37h 34mAmerican Airlines

Deal found 29/6$1,089

Tue 12/810:00AKL - ORD

3 stops53h 28mSingapore Airlines

Deal found 30/6$2,785

Tue 12/800:25AKL - ORD

2 stops38h 35mTurkish Airlines

Deal found 29/6$5,432

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

Thu 25/9

15:50-12:15

1 stop37h 25m

Chicago O'Hare Intl

Sat 25/10

17:17-09:25

1 stop22h 08m

$1,436

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 25/9

06:35-16:42

2 stops27h 07m

Chicago O'Hare Intl

Sat 25/10

15:40-16:50

2 stops31h 10m

$1,527

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 13/8

13:55-05:40

2 stops32h 45m

Chicago O'Hare Intl

Wed 20/8

07:05-12:40

2 stops36h 35m

$1,529

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 14/7

13:50-17:05

2 stops20h 15m

Chicago O'Hare Intl

Tue 29/7

16:20-07:10

2 stops21h 50m

$1,954

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 29/10

20:10-20:25

1 stop18h 15m

Chicago O'Hare Intl

Tue 11/11

13:00-05:00

1 stop21h 00m

$1,956

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 11/8

06:00-17:08

2 stops28h 08m

Chicago O'Hare Intl

Tue 9/9

18:47-14:05

2 stops26h 18m

$2,096

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 18/9

06:35-16:42

2 stops27h 07m

$771

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 8/11

07:00-21:59

3 stops33h 59m

$782

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 18/9

13:50-15:03

1 stop18h 13m

$1,018

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 13/8

06:45-19:12

2 stops29h 27m

$1,032

Flights are sorted by cheapest return flights first.

Deals found on 30/6

Showing 1-10 of 13 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 22 hours 54 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, Air New Zealand and United Airlines.

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

Read reviews from past customers who have flown Singapore Airlines, Air New Zealand, andQantas Airways 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.

Singapore Airlines

8.1

Very Good

1,319 reviews

Check prices

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Singapore Airlines

8.1

Very Good

1,319 reviews

Singapore Airlines

8.1

Very Good

1,319 reviews

Check prices

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Air New Zealand

8.0

Very Good

486 reviews

Singapore Airlines

8.1

Very Good

1,319 reviews

Check prices

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Qantas Airways

7.5

Good

869 reviews

Singapore Airlines

8.1

Very Good

1,319 reviews

Check prices

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

United Airlines

7.4

Good

8,852 reviews

Singapore Airlines

8.1

Very Good

1,319 reviews

Check prices

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Turkish Airlines

7.3

Good

3,884 reviews

Singapore Airlines

8.1

Very Good

1,319 reviews

Check prices

Reviews

1 / 20

6.0

Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

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 $160, while return flights cost around $144.
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 (22 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

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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$771+ 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 18/9. 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 30 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 30 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 30 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 30 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 27 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

Read reviews from past customers who have flown Singapore Airlines, Air New Zealand, andQantas Airways 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.

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 30 June 2025.