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 $163, 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 (25 hours 44 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).

$1,040+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	$1,934
One-way from	$1,040
Popular in	April
Cheapest in	February
Average price	$2,473

10/6-16/6
4 total stops
69h 31m total
Auckland to Chicago

Search Deals

Air Canada
19/5
1 total stop
20h 42m total
Auckland to Chicago

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($115 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($66 potential savings vs. average return price).

Search Deals

Average for return flights in April 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 April 2025.

Fri 21/1106:25AKL - ORD

2 stops27h 14mAir Canada

Thu 15/121:15ORD - AKL

2 stops42h 45mAir Canada

Deal found 28/4$1,914

Tue 10/613:55AKL - ORD

2 stops33h 47mMultiple Airlines

Mon 16/607:56ORD - AKL

2 stops35h 44mMultiple Airlines

Deal found 30/4$1,934

Thu 29/515:50AKL - ORD

2 stops31h 16mAmerican Airlines

Mon 9/607:35ORD - AKL

2 stops33h 50mAmerican Airlines

Deal found 30/4$2,038

Thu 29/506:00AKL - ORD

2 stops26h 55mQantas Airways

Mon 9/617:51ORD - AKL

2 stops27h 14mQantas Airways

Deal found 30/4$2,068

Thu 20/1116:05AKL - ORD

2 stops25h 55mAir Tahiti Nui

Fri 16/114:14ORD - AKL

2 stops28h 26mAir Tahiti Nui

Deal found 28/4$2,228

Thu 20/1114:55AKL - ORD

1 stop41h 05mCathay Pacific

Tue 13/114:40ORD - AKL

1 stop27h 45mCathay Pacific

Deal found 28/4$2,248

Thu 20/1123:30AKL - ORD

2 stops24h 34mAlaska Airlines

Thu 15/114:05ORD - AKL

2 stops36h 15mAlaska Airlines

Deal found 28/4$2,332

Sat 11/1014:50AKL - ORD

1 stop18h 05mUnited Airlines

Sat 11/1019:55ORD - AKL

1 stop39h 35mUnited Airlines

Deal found 29/4$2,352

Thu 29/513:50AKL - ORD

1 stop32h 39mAir New Zealand

Mon 9/619:47ORD - AKL

1 stop41h 13mAir New Zealand

Deal found 29/4$2,500

Tue 10/609:40AKL - ORD

1 stop28h 20mEVA Air

Sun 15/600:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 30/4$3,098

Fri 21/1114:50AKL - ORD

2 stops20h 57mDelta

Tue 13/112:15ORD - AKL

2 stops25h 40mDelta

Deal found 28/4$3,171

Fri 21/1122:10AKL - ORD

2 stops49h 52mChina Southern

Thu 15/112:25ORD - AKL

3 stops56h 50mChina Southern

Deal found 28/4$3,251

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 April 2025.

Tue 10/613:55AKL - ORD

2 stops33h 47mMultiple Airlines

Mon 16/607:56ORD - AKL

2 stops35h 44mMultiple Airlines

Deal found 30/4$1,934

Thu 29/515:50AKL - ORD

2 stops31h 16mAmerican Airlines

Mon 9/607:35ORD - AKL

2 stops33h 50mAmerican Airlines

Deal found 30/4$2,038

Tue 10/619:45AKL - ORD

1 stop20h 28mAir Canada

Mon 16/615:35ORD - AKL

2 stops30h 20mAir Canada

Deal found 30/4$2,057

Thu 29/506:00AKL - ORD

2 stops26h 55mQantas Airways

Mon 9/617:51ORD - AKL

2 stops27h 14mQantas Airways

Deal found 30/4$2,068

Wed 4/610:15AKL - ORD

1 stop45h 10mCathay Pacific

Sat 21/616:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 30/4$2,250

Thu 29/513:50AKL - ORD

1 stop32h 39mAir New Zealand

Mon 9/619:47ORD - AKL

1 stop41h 13mAir New Zealand

Deal found 29/4$2,500

Thu 29/513:50AKL - ORD

1 stop32h 14mUnited Airlines

Mon 9/621:09ORD - AKL

1 stop41h 01mUnited Airlines

Deal found 30/4$2,594

Tue 10/609:40AKL - ORD

1 stop28h 20mEVA Air

Sun 15/600:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 30/4$3,098

Wed 25/621:25AKL - ORD

3 stops49h 45mChina Southern

Sun 6/715:21ORD - AKL

2 stops55h 14mChina Southern

Deal found 28/4$12,296

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

Wed 30/413:25AKL - ORD

1 stop42h 00mCathay Pacific

Tue 20/516:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 29/4$2,910

Tue 6/500:25AKL - ORD

2 stops37h 35mMultiple Airlines

Fri 9/517:45ORD - AKL

1 stop46h 40mMultiple Airlines

Deal found 29/4$20,840

Wed 7/507:00AKL - ORD

2 stops27h 08mUnited Airlines

Fri 9/519:56ORD - AKL

1 stop42h 14mUnited Airlines

Deal found 29/4$12,222

Wed 7/507:30AKL - ORD

2 stops33h 29mQantas Airways

Fri 9/520:00ORD - AKL

2 stops48h 45mQantas Airways

Deal found 29/4$12,422

Wed 7/513:25AKL - ORD

1 stop42h 00mCathay Pacific

Fri 9/516:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 29/4$13,171

Wed 7/520:15AKL - ORD

1 stop25h 49mAir New Zealand

Fri 9/521:14ORD - AKL

1 stop39h 46mAir New Zealand

Deal found 29/4$13,963

Wed 7/521:25AKL - ORD

3 stops49h 42mChina Southern

Fri 9/517:38ORD - AKL

2 stops52h 57mChina Southern

Deal found 29/4$14,484

Sun 11/521:25AKL - ORD

3 stops49h 42mChina Southern

Mon 19/516:51ORD - AKL

3 stops53h 44mChina Southern

Deal found 30/4$4,083

Thu 29/515:50AKL - ORD

2 stops31h 16mAmerican Airlines

Mon 9/607:35ORD - AKL

2 stops33h 50mAmerican Airlines

Deal found 30/4$2,038

Thu 29/506:00AKL - ORD

2 stops26h 55mQantas Airways

Mon 9/617:51ORD - AKL

2 stops27h 14mQantas Airways

Deal found 30/4$2,068

Thu 29/513:25AKL - ORD

1 stop42h 00mMultiple Airlines

Mon 9/609:12ORD - AKL

2 stops33h 28mMultiple Airlines

Deal found 30/4$2,119

Thu 29/513:50AKL - ORD

1 stop32h 39mAir New Zealand

Mon 9/619:47ORD - AKL

1 stop41h 13mAir New Zealand

Deal found 29/4$2,500

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 April 2025.

Mon 19/519:45AKL - ORD

1 stop20h 42mAir Canada

Deal found 29/4$1,040

Mon 19/506:10AKL - ORD

2 stops26h 45mQantas Airways

Deal found 29/4$1,043

Sat 17/513:50AKL - ORD

1 stop32h 21mUnited Airlines

Deal found 29/4$1,509

Mon 19/506:00AKL - ORD

3 stops30h 30mMultiple Airlines

Deal found 29/4$2,117

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

Tue 10/6

13:55-06:42

2 stops33h 47m

Chicago O'Hare Intl

Mon 16/6

07:56-12:40

2 stops35h 44m

$1,934

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

15:50-06:06

2 stops31h 16m

Chicago O'Hare Intl

Mon 9/6

07:35-10:25

2 stops33h 50m

$2,038

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 10/6

19:45-23:13

1 stop20h 28m

Chicago O'Hare Intl

Mon 16/6

15:35-14:55

2 stops30h 20m

$2,057

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

06:00-15:55

2 stops26h 55m

Chicago O'Hare Intl

Mon 9/6

17:51-14:05

2 stops27h 14m

$2,068

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 4/6

10:15-14:25

1 stop45h 10m

Chicago O'Hare Intl

Sat 21/6

16:00-09:50

1 stop48h 50m

$2,250

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 9/10

16:20-23:43

2 stops25h 23m

Chicago O'Hare Intl

Tue 21/10

17:51-13:10

2 stops25h 19m

$2,275

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 11/10

14:50-14:55

1 stop18h 05m

Chicago O'Hare Intl

Sat 11/10

19:55-05:30

1 stop39h 35m

$2,352

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

13:50-05:29

1 stop32h 39m

Chicago O'Hare Intl

Mon 9/6

19:47-06:00

1 stop41h 13m

$2,500

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Tue 10/6

09:40-21:00

1 stop28h 20m

Chicago O'Hare Intl

Sun 15/6

00:30-09:15

1 stop39h 45m

$3,098

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sun 12/10

14:15-15:05

1 stop42h 50m

Chicago O'Hare Intl

Tue 21/10

13:35-03:45

2 stops44h 10m

$4,046

Flights are sorted by cheapest return flights first.

Deals found on 29/4

Showing 1-10 of 17 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 77 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 44 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.

Qantas Airways

From $894

United Airlines

From $929

Air New Zealand

From $1,106

Air Canada

From $890

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

See what other customers who have flown with EVA Air, Air New Zealand and Qantas Airways to Chicago have to say. 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.

EVA Air

8.4

Very Good

1,186 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,Apr 2025

SFO - TPE

Great experience. Check in process was excellent - both online and bag drop

EVA Air

8.4

Very Good

1,186 reviews

EVA Air

8.4

Very Good

1,186 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,Apr 2025

SFO - TPE

Great experience. Check in process was excellent - both online and bag drop

Air New Zealand

8.0

Very Good

472 reviews

EVA Air

8.4

Very Good

1,186 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,Apr 2025

SFO - TPE

Great experience. Check in process was excellent - both online and bag drop

Qantas Airways

7.5

Good

829 reviews

EVA Air

8.4

Very Good

1,186 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,Apr 2025

SFO - TPE

Great experience. Check in process was excellent - both online and bag drop

Cathay Pacific

7.5

Good

852 reviews

EVA Air

8.4

Very Good

1,186 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,Apr 2025

SFO - TPE

Great experience. Check in process was excellent - both online and bag drop

China Southern

7.5

Good

96 reviews

EVA Air

8.4

Very Good

1,186 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Dale,Apr 2025

SFO - TPE

Great experience. Check in process was excellent - both online and bag drop

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 $163, 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 (25 hours 44 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

Flights from Auckland to Honolulu

Flights from Auckland to San Francisco

Flights from Auckland to Los Angeles

Flights from Auckland to John F Kennedy Intl

Flights from Christchurch to San Francisco

Flights from Auckland to George Bush Intcntl

Flights from Los Angeles to Las Vegas

Flights from Los Angeles to Denver

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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$1,040+ 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 19/5. 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 April 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 April 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 April 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 April 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 25 April 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

See what other customers who have flown with EVA Air, Air New Zealand and Qantas Airways to Chicago have to say. 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 30 April 2025.