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 $166, while return flights cost around $170.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around $108, however they can be found for as little as $100.

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 (24 hours 43 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).

$793+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	$1,709
One-way from	$793
Popular in	April
Cheapest in	February
Average price	$2,509

29/5-5/6
2 total stops
60h 44m total
Auckland to Chicago

Search Deals

6/5
3 total stops
38h 41m total
Auckland to Chicago

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($143 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($70 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 15 April 2025.

Thu 29/520:15AKL - ORD

1 stop32h 21mMultiple Airlines

Thu 5/608:37ORD - AKL

1 stop28h 23mMultiple Airlines

Deal found 14/4$1,709

Wed 30/415:50AKL - ORD

2 stops31h 27mAmerican Airlines

Tue 20/522:37ORD - AKL

1 stop42h 48mAmerican Airlines

Deal found 14/4$1,877

Sat 22/1119:45AKL - ORD

1 stop30h 55mUnited Airlines

Mon 24/1107:15ORD - AKL

1 stop27h 45mUnited Airlines

Deal found 13/4$2,025

Sat 14/613:25AKL - ORD

2 stops27h 10mQantas Airways

Sat 26/718:20ORD - AKL

2 stops26h 50mQantas Airways

Deal found 14/4$2,049

Wed 30/413:25AKL - ORD

1 stop42h 00mCathay Pacific

Sun 4/516:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 14/4$2,153

Thu 29/519:40AKL - ORD

1 stop21h 33mAir New Zealand

Mon 9/621:40ORD - AKL

1 stop39h 20mAir New Zealand

Deal found 14/4$2,410

Sat 22/1106:25AKL - ORD

2 stops29h 13mAir Canada

Mon 24/1114:00ORD - AKL

3 stops31h 50mAir Canada

Deal found 13/4$2,979

Thu 29/521:25AKL - ORD

2 stops48h 45mChina Southern

Thu 5/618:35ORD - AKL

3 stops52h 00mChina Southern

Deal found 14/4$3,129

Sat 22/1114:50AKL - ORD

3 stops26h 02mDelta

Mon 24/1112:17ORD - AKL

3 stops25h 38mDelta

Deal found 13/4$3,150

Thu 29/509:40AKL - ORD

1 stop28h 20mEVA Air

Sun 8/600:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 14/4$3,906

Sat 14/610:00AKL - ORD

3 stops54h 25mSingapore Airlines

Sat 26/711:05ORD - AKL

3 stops52h 20mSingapore Airlines

Deal found 14/4$6,874

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 15 April 2025.

Thu 29/520:15AKL - ORD

1 stop32h 21mMultiple Airlines

Thu 5/608:37ORD - AKL

1 stop28h 23mMultiple Airlines

Deal found 14/4$1,709

Wed 30/415:50AKL - ORD

2 stops31h 27mAmerican Airlines

Tue 20/522:37ORD - AKL

1 stop42h 48mAmerican Airlines

Deal found 14/4$1,877

Wed 30/406:45AKL - ORD

2 stops34h 14mQantas Airways

Sun 4/515:17ORD - AKL

2 stops33h 43mQantas Airways

Deal found 14/4$2,025

Wed 30/413:25AKL - ORD

1 stop42h 00mCathay Pacific

Sun 4/516:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 14/4$2,153

Thu 29/519:40AKL - ORD

1 stop21h 33mAir New Zealand

Mon 9/621:40ORD - AKL

1 stop39h 20mAir New Zealand

Deal found 14/4$2,410

Thu 29/513:50AKL - ORD

2 stops27h 35mUnited Airlines

Thu 5/616:40ORD - AKL

1 stop20h 20mUnited Airlines

Deal found 14/4$2,463

Thu 29/521:25AKL - ORD

2 stops48h 45mChina Southern

Thu 5/618:35ORD - AKL

3 stops52h 00mChina Southern

Deal found 14/4$3,129

Wed 30/419:55AKL - ORD

2 stops50h 51mAir Canada

Tue 20/514:00ORD - AKL

3 stops32h 05mAir Canada

Deal found 14/4$3,538

Thu 29/509:40AKL - ORD

1 stop28h 20mEVA Air

Sun 8/600:30ORD - AKL

1 stop39h 45mEVA Air

Deal found 14/4$3,906

Sat 14/610:00AKL - ORD

3 stops54h 25mSingapore Airlines

Sat 26/711:05ORD - AKL

3 stops52h 20mSingapore Airlines

Deal found 14/4$6,874

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 15 April 2025 and is based on user searches.

Fri 25/407:30AKL - ORD

2 stops33h 29mQantas Airways

Sat 24/515:15ORD - AKL

2 stops29h 55mQantas Airways

Deal found 15/4$2,289

Fri 25/422:00AKL - ORD

1 stop25h 25mAir New Zealand

Sat 24/520:20ORD - AKL

1 stop40h 10mAir New Zealand

Deal found 15/4$2,512

Fri 25/419:40AKL - ORD

2 stops31h 06mUnited Airlines

Sat 24/520:20ORD - AKL

1 stop40h 10mUnited Airlines

Deal found 15/4$2,577

Fri 25/422:00AKL - ORD

3 stops38h 30mMultiple Airlines

Sat 24/518:59ORD - AKL

2 stops24h 41mMultiple Airlines

Deal found 15/4$3,467

Fri 25/419:55AKL - ORD

3 stops53h 08mAir Canada

Sat 24/514:00ORD - AKL

3 stops33h 50mAir Canada

Deal found 15/4$5,529

Wed 30/415:50AKL - ORD

2 stops31h 27mAmerican Airlines

Tue 20/522:37ORD - AKL

1 stop42h 48mAmerican Airlines

Deal found 14/4$1,877

Wed 30/406:45AKL - ORD

2 stops34h 14mQantas Airways

Sun 4/515:17ORD - AKL

2 stops33h 43mQantas Airways

Deal found 14/4$2,025

Wed 30/413:25AKL - ORD

1 stop42h 00mCathay Pacific

Sun 4/516:00ORD - AKL

1 stop48h 50mCathay Pacific

Deal found 14/4$2,153

Wed 30/419:55AKL - ORD

2 stops50h 51mAir Canada

Tue 20/514:00ORD - AKL

3 stops32h 05mAir Canada

Deal found 14/4$3,538

Thu 29/520:15AKL - ORD

1 stop32h 21mMultiple Airlines

Thu 5/608:37ORD - AKL

1 stop28h 23mMultiple Airlines

Deal found 14/4$1,709

Thu 29/519:40AKL - ORD

1 stop21h 33mAir New Zealand

Mon 9/621:40ORD - AKL

1 stop39h 20mAir New Zealand

Deal found 14/4$2,410

Thu 29/513:50AKL - ORD

2 stops27h 35mUnited Airlines

Thu 5/616:40ORD - AKL

1 stop20h 20mUnited Airlines

Deal found 14/4$2,463

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 15 April 2025.

Tue 6/513:55AKL - ORD

3 stops38h 41mMultiple Airlines

Deal found 13/4$793

Wed 30/413:25AKL - ORD

2 stops27h 34mQantas Airways

Deal found 14/4$1,000

Wed 21/519:45AKL - ORD

1 stop26h 26mAir Canada

Deal found 14/4$1,033

Sat 17/514:55AKL - ORD

1 stop26h 04mAmerican Airlines

Deal found 14/4$1,072

Mon 5/513:50AKL - ORD

1 stop24h 26mAir New Zealand

Deal found 13/4$1,203

Sat 17/513:00AKL - ORD

3 stops27h 17mDelta

Deal found 14/4$2,141

Wed 30/421:25AKL - ORD

3 stops49h 52mChina Southern

Deal found 14/4$2,154

Mon 28/400:25AKL - ORD

2 stops55h 40mQatar Airways

Deal found 14/4$2,768

Tue 29/420:15AKL - ORD

3 stops26h 31mUnited Airlines

Deal found 14/4$6,577

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 29/5

20:15-11:36

1 stop32h 21m

Chicago O'Hare Intl

Thu 5/6

08:37-06:00

1 stop28h 23m

$1,709

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 30/4

15:50-06:17

2 stops31h 27m

Chicago O'Hare Intl

Tue 20/5

22:37-10:25

1 stop42h 48m

$1,877

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 30/4

06:45-23:59

2 stops34h 14m

Chicago O'Hare Intl

Sun 4/5

15:17-18:00

2 stops33h 43m

$2,025

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 30/4

13:25-14:25

1 stop42h 00m

Chicago O'Hare Intl

Sun 4/5

16:00-09:50

1 stop48h 50m

$2,153

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

19:40-00:13

1 stop21h 33m

Chicago O'Hare Intl

Mon 9/6

21:40-06:00

1 stop39h 20m

$2,410

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

13:50-00:25

2 stops27h 35m

Chicago O'Hare Intl

Thu 5/6

16:40-06:00

1 stop20h 20m

$2,463

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

21:25-05:10

2 stops48h 45m

Chicago O'Hare Intl

Thu 5/6

18:35-15:35

3 stops52h 00m

$3,129

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Wed 30/4

19:55-05:46

2 stops50h 51m

Chicago O'Hare Intl

Tue 20/5

14:00-15:05

3 stops32h 05m

$3,538

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Thu 29/5

09:40-21:00

1 stop28h 20m

Chicago O'Hare Intl

Sun 8/6

00:30-09:15

1 stop39h 45m

$3,906

AucklandChicago

AKL - ORD

AKLORD

Auckland Intl

Sat 14/6

10:00-23:25

3 stops54h 25m

Chicago O'Hare Intl

Sat 26/7

11:05-08:25

3 stops52h 20m

$6,874

Flights are sorted by cheapest return flights first.

Deals found on 13/4

Showing 1-10 of 19 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 24 hours 43 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, Singapore Airlines and Delta 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

1,176 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

EVA Air

8.4

Very Good

1,176 reviews

EVA Air

8.4

Very Good

1,176 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

Singapore Airlines

8.1

Very Good

1,288 reviews

EVA Air

8.4

Very Good

1,176 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

Delta

8.0

Very Good

7,917 reviews

EVA Air

8.4

Very Good

1,176 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

Air New Zealand

8.0

Very Good

464 reviews

EVA Air

8.4

Very Good

1,176 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

Qantas Airways

7.5

Good

818 reviews

EVA Air

8.4

Very Good

1,176 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

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 $166, while return flights cost around $170.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around $108, however they can be found for as little as $100.
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 (24 hours 43 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

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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Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$793+ 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 6/5. 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 15 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 15 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 15 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 15 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 11 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, Singapore Airlines and Delta 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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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 15 April 2025.