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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost $157, while return flights cost around $146.

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 (18 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).

$757+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	$1,418
One-way from	$757
Popular in	April
Cheapest in	February
Average price	$2,109

American Airlines
3/2-24/2
3 total stops
50h 30m total
Auckland to Chicago

Search Deals

17/10
3 total stops
35h 27m total
Auckland to Chicago

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($135 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($63 potential savings vs. average return price).

Search Deals

Average for return flights in September 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 September 2025.

Thu 25/915:50AKL - ORD

2 stops30h 40mAmerican Airlines

Sat 25/1016:17ORD - AKL

1 stop21h 53mAmerican Airlines

Deal found 12/9$1,448

Fri 26/915:50AKL - ORD

2 stops31h 11mAmerican Airlines

Sat 25/1017:17ORD - AKL

1 stop20h 53mAmerican Airlines

Deal found 12/9$1,478

Mon 6/1015:50AKL - ORD

2 stops31h 44mAmerican Airlines

Tue 18/1111:45ORD - AKL

1 stop27h 40mAmerican Airlines

Deal found 12/9$1,500

Sun 19/1015:50AKL - ORD

1 stop38h 31mAmerican Airlines

Tue 4/1117:40ORD - AKL

2 stops44h 30mAmerican Airlines

Deal found 13/9$1,507

Fri 26/916:25AKL - ORD

1 stop37h 16mAmerican Airlines

Fri 10/1006:03ORD - AKL

1 stop34h 22mAmerican Airlines

Deal found 12/9$1,649

Mon 22/1213:20AKL - ORD

2 stops20h 25mAmerican Airlines

Mon 12/108:40ORD - AKL

1 stop30h 25mAmerican Airlines

Deal found 12/9$1,661

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 September 2025.

Tue 3/213:20AKL - ORD

2 stops22h 40mAmerican Airlines

Tue 24/207:18ORD - AKL

1 stop31h 47mAmerican Airlines

Deal found 12/9$1,419

Tue 10/319:55AKL - ORD

1 stop18h 15mUnited Airlines

Wed 11/308:50ORD - AKL

1 stop27h 05mUnited Airlines

Deal found 12/9$1,550

Tue 3/207:00AKL - ORD

2 stops28h 38mAir Canada

Tue 24/217:50ORD - AKL

2 stops46h 10mAir Canada

Deal found 11/9$1,579

Fri 26/915:50AKL - ORD

2 stops31h 11mAmerican Airlines

Sat 25/1017:17ORD - AKL

1 stop20h 53mAmerican Airlines

Deal found 12/9$1,478

Fri 30/114:00AKL - ORD

1 stop21h 38mAir Canada

Fri 27/215:40ORD - AKL

1 stop24h 20mAir Canada

Deal found 11/9$1,579

Mon 6/1015:50AKL - ORD

2 stops31h 44mAmerican Airlines

Tue 18/1111:45ORD - AKL

1 stop27h 40mAmerican Airlines

Deal found 13/9$1,502

Fri 30/114:00AKL - ORD

1 stop19h 41mAir Canada

Wed 25/215:40ORD - AKL

1 stop24h 20mAir Canada

Deal found 11/9$1,579

Sun 19/1015:50AKL - ORD

1 stop38h 31mAmerican Airlines

Tue 4/1117:40ORD - AKL

2 stops44h 30mAmerican Airlines

Deal found 13/9$1,507

Sun 1/207:00AKL - ORD

2 stops26h 41mAir Canada

Sun 22/215:40ORD - AKL

1 stop24h 20mAir Canada

Deal found 11/9$1,579

Wed 18/206:15AKL - ORD

2 stops27h 26mAir Canada

Wed 25/208:45ORD - AKL

2 stops31h 15mAir Canada

Deal found 14/9$1,584

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

Thu 25/915:50AKL - ORD

2 stops30h 40mAmerican Airlines

Sat 25/1016:17ORD - AKL

1 stop21h 53mAmerican Airlines

Deal found 12/9$1,448

Fri 26/915:50AKL - ORD

2 stops31h 11mAmerican Airlines

Sat 25/1017:17ORD - AKL

1 stop20h 53mAmerican Airlines

Deal found 12/9$1,478

Fri 26/916:25AKL - ORD

1 stop37h 16mAmerican Airlines

Fri 10/1006:03ORD - AKL

1 stop34h 22mAmerican Airlines

Deal found 12/9$1,649

Mon 6/1015:50AKL - ORD

2 stops31h 44mAmerican Airlines

Tue 18/1111:45ORD - AKL

1 stop27h 40mAmerican Airlines

Deal found 12/9$1,500

Sun 19/1015:50AKL - ORD

1 stop38h 31mAmerican Airlines

Tue 4/1117:40ORD - AKL

2 stops44h 30mAmerican Airlines

Deal found 13/9$1,507

Tue 28/1010:10AKL - ORD

1 stop45h 50mCathay Pacific

Tue 4/1114:40ORD - AKL

1 stop27h 45mCathay Pacific

Deal found 13/9$1,830

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 September 2025.

Fri 17/1006:50AKL - ORD

3 stops35h 27mMultiple Airlines

Deal found 12/9$757

Sat 18/1020:15AKL - ORD

1 stop21h 44mMultiple Airlines

Deal found 12/9$871

Fri 14/1115:10AKL - ORD

2 stops26h 50mMultiple Airlines

Deal found 12/9$888

Mon 27/1015:10AKL - ORD

2 stops26h 49mMultiple Airlines

Deal found 12/9$899

Thu 13/1116:05AKL - ORD

3 stops27h 10mMultiple Airlines

Deal found 12/9$904

Thu 16/1019:40AKL - ORD

1 stop22h 46mMultiple Airlines

Deal found 12/9$911

Sun 19/1015:10AKL - ORD

3 stops51h 49mMultiple Airlines

Deal found 12/9$919

Fly from

Route

Departure

Return

Price

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 3/2

13:20-17:00

2 stops22h 40m

Chicago O'Hare Intl

Tue 24/2

07:18-10:05

1 stop31h 47m

$1,419

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 26/9

15:50-06:01

2 stops31h 11m

Chicago O'Hare Intl

Sat 25/10

17:17-08:10

1 stop20h 53m

$1,478

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Mon 6/10

15:50-05:34

2 stops31h 44m

Chicago O'Hare Intl

Tue 18/11

11:45-10:25

1 stop27h 40m

$1,502

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 19/10

15:50-12:21

1 stop38h 31m

Chicago O'Hare Intl

Tue 4/11

17:40-09:10

2 stops44h 30m

$1,507

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 10/3

19:55-20:10

1 stop18h 15m

Chicago O'Hare Intl

Wed 11/3

08:50-05:55

1 stop27h 05m

$1,550

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 3/2

07:00-16:38

2 stops28h 38m

Chicago O'Hare Intl

Tue 24/2

17:50-11:00

2 stops46h 10m

$1,579

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 30/1

14:00-16:38

1 stop21h 38m

Chicago O'Hare Intl

Fri 27/2

15:40-11:00

1 stop24h 20m

$1,579

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Fri 30/1

14:00-14:41

1 stop19h 41m

Chicago O'Hare Intl

Wed 25/2

15:40-11:00

1 stop24h 20m

$1,579

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 1/2

07:00-14:41

2 stops26h 41m

Chicago O'Hare Intl

Sun 22/2

15:40-11:00

1 stop24h 20m

$1,579

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 18/2

06:15-14:41

2 stops27h 26m

Chicago O'Hare Intl

Wed 25/2

08:45-11:00

2 stops31h 15m

$1,584

Flights are sorted by cheapest return flights first.

Deals found on 14/9

Showing 1-10 of 16 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 24 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 18 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, 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, United Airlines and Qantas Airways.

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

505 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

Air New Zealand

8.0

Very Good

505 reviews

Air New Zealand

8.0

Very Good

505 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

Qantas Airways

7.5

Good

905 reviews

Air New Zealand

8.0

Very Good

505 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

United Airlines

7.4

Good

8,931 reviews

Air New Zealand

8.0

Very Good

505 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

American Airlines

7.2

Good

10,000 reviews

Air New Zealand

8.0

Very Good

505 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

Air Canada

7.1

Good

10,000 reviews

Air New Zealand

8.0

Very Good

505 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2025

AKL - SFO

Flight was delayed an hour. We had just flown Air NZ on a 12- hour flight from AKL so the extra delay on this connecting flight wasn’t welcomed.

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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost $157, while return flights cost around $146.
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 (18 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

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Flights from Midway

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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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$757+ 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 17/10. 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 September 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 September 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 September 2025.

Cheapflights Fare Finder

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 12 September 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 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.

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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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 September 2025.