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, Qantas Airways 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 $50, while return flights cost around $177.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around $134, however they can be found for as little as $115.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Sydney Kingsford Smith offers the quickest one-way flight (21 hours 41 minutes).

Which airport is closest to River North?

f being close to River North is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

Does Chicago O'Hare Intl have car hire?

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).

$681+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Return from	$1,481
One-way from	$681
Popular in	December
Cheapest in	February
Average price	$1,597

Air Canada
28/9-8/10
2 total stops
45h 15m total
Sydney to Chicago

Search Deals

17/10
2 total stops
46h 39m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 22% potential increase in price ($705 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($116 potential savings vs. average return price).

Search Deals

Average for return flights in August 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 29 August 2025.

Sun 28/909:20SYD - ORD

1 stop20h 40mAir Canada

Wed 8/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Sat 4/1009:20SYD - ORD

1 stop20h 40mAir Canada

Sat 11/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,505

Sat 4/1009:20SYD - ORD

1 stop20h 40mAir Canada

Fri 10/1021:12ORD - SYD

2 stops43h 08mAir Canada

Deal found 27/8$1,516

Sat 4/1009:20SYD - ORD

1 stop22h 22mAir Canada

Wed 8/1013:27ORD - SYD

2 stops26h 53mAir Canada

Deal found 27/8$1,554

Sat 13/913:45SYD - ORD

3 stops35h 57mMultiple Airlines

Wed 17/909:00ORD - SYD

3 stops35h 45mMultiple Airlines

Deal found 28/8$1,698

Mon 15/909:10SYD - ORD

1 stop24h 55mAmerican Airlines

Mon 22/911:56ORD - SYD

1 stop28h 09mAmerican Airlines

Deal found 27/8$1,741

Mon 20/1010:20SYD - ORD

2 stops35h 15mMultiple Airlines

Mon 27/1021:00ORD - SYD

3 stops44h 50mMultiple Airlines

Deal found 27/8$1,813

Thu 16/1019:30SYD - ORD

2 stops41h 15mMultiple Airlines

Tue 21/1000:30ORD - SYD

2 stops39h 10mMultiple Airlines

Deal found 28/8$1,944

Thu 25/1216:00SYD - ORD

2 stops36h 18mAir Canada

Fri 23/115:40ORD - SYD

1 stop24h 55mAir Canada

Deal found 29/8$2,014

Mon 20/1010:25SYD - MDW

2 stops24h 00mDelta

Mon 27/1013:48MDW - SYD

2 stops25h 42mDelta

Deal found 27/8$2,063

Tue 30/909:25SYD - MDW

2 stops23h 10mDelta

Wed 12/1110:47MDW - SYD

2 stops28h 43mDelta

Deal found 27/8$2,360

Sat 11/1010:25SYD - MDW

2 stops27h 49mDelta

Sat 18/1013:11MDW - SYD

2 stops26h 24mDelta

Deal found 27/8$2,511

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 29 August 2025.

Thu 2/1009:20SYD - ORD

1 stop22h 22mAir Canada

Fri 10/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Thu 27/1110:40SYD - MDW

2 stops22h 59mDelta

Mon 8/1209:30MDW - SYD

2 stops30h 00mDelta

Deal found 26/8$2,063

Fri 3/1009:20SYD - ORD

1 stop20h 40mAir Canada

Wed 8/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Wed 1/1009:20SYD - ORD

1 stop22h 22mAir Canada

Fri 10/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Sun 28/909:20SYD - ORD

2 stops22h 31mAir Canada

Wed 8/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Mon 29/909:20SYD - ORD

1 stop20h 40mAir Canada

Fri 10/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Mon 20/1010:25SYD - MDW

2 stops24h 00mDelta

Mon 27/1013:48MDW - SYD

2 stops25h 42mDelta

Deal found 27/8$2,063

Tue 30/909:20SYD - ORD

1 stop20h 40mAir Canada

Fri 10/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Sat 4/1009:20SYD - ORD

2 stops22h 31mAir Canada

Sat 11/1013:27ORD - SYD

2 stops26h 53mAir Canada

Deal found 27/8$1,505

Tue 30/909:25SYD - MDW

2 stops23h 10mDelta

Wed 12/1110:47MDW - SYD

2 stops28h 43mDelta

Deal found 27/8$2,360

Wed 8/1010:25SYD - MDW

2 stops23h 18mDelta

Wed 22/1009:35MDW - SYD

2 stops30h 00mDelta

Deal found 27/8$2,360

Wed 10/909:25SYD - MDW

2 stops23h 12mDelta

Mon 3/1110:30MDW - SYD

2 stops29h 00mDelta

Deal found 27/8$2,511

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 29 August 2025 and is based on user searches.

Wed 10/909:20SYD - ORD

3 stops27h 12mMultiple Airlines

Mon 3/1109:40ORD - SYD

3 stops33h 50mMultiple Airlines

Deal found 27/8$2,135

Thu 11/906:00SYD - ORD

3 stops44h 51mMultiple Airlines

Mon 13/1011:41ORD - SYD

3 stops28h 39mMultiple Airlines

Deal found 27/8$2,387

Sat 13/913:45SYD - ORD

3 stops35h 57mMultiple Airlines

Wed 17/909:00ORD - SYD

3 stops35h 45mMultiple Airlines

Deal found 28/8$1,698

Sun 14/909:20SYD - ORD

1 stop20h 40mAir Canada

Fri 19/908:51ORD - SYD

1 stop31h 29mAir Canada

Deal found 27/8$1,554

Mon 15/909:10SYD - ORD

1 stop24h 55mAmerican Airlines

Mon 22/911:56ORD - SYD

1 stop28h 09mAmerican Airlines

Deal found 27/8$1,741

Mon 15/908:55SYD - ORD

1 stop39h 10mJapan Airlines

Sun 21/901:05ORD - SYD

1 stop38h 15mJapan Airlines

Deal found 27/8$2,396

Tue 16/909:20SYD - ORD

3 stops27h 12mMultiple Airlines

Fri 5/1207:35ORD - SYD

3 stops33h 00mMultiple Airlines

Deal found 26/8$2,282

Tue 16/909:20SYD - ORD

3 stops27h 12mMultiple Airlines

Tue 14/1006:00ORD - SYD

3 stops34h 20mMultiple Airlines

Deal found 27/8$2,406

Tue 16/910:15SYD - ORD

2 stops35h 41mChina Southern

Mon 22/918:00ORD - SYD

3 stops47h 25mChina Southern

Deal found 27/8$2,445

Wed 17/909:20SYD - ORD

3 stops27h 12mMultiple Airlines

Sat 6/1210:18ORD - SYD

3 stops33h 12mMultiple Airlines

Deal found 27/8$2,068

Sun 28/909:20SYD - ORD

1 stop20h 40mAir Canada

Wed 8/1015:45ORD - SYD

1 stop24h 35mAir Canada

Deal found 27/8$1,481

Tue 30/909:25SYD - MDW

2 stops23h 10mDelta

Wed 12/1110:47MDW - SYD

2 stops28h 43mDelta

Deal found 27/8$2,360

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 29 August 2025.

Fri 17/1017:20SYD - ORD

2 stops46h 39mMultiple Airlines

Deal found 28/8$681

Wed 22/1017:20SYD - ORD

3 stops46h 33mMultiple Airlines

Deal found 28/8$691

Sun 19/1017:20SYD - ORD

3 stops46h 24mMultiple Airlines

Deal found 28/8$711

Wed 15/1017:20SYD - ORD

3 stops47h 06mMultiple Airlines

Deal found 28/8$725

Wed 15/1017:20SYD - MDW

3 stops38h 45mMultiple Airlines

Deal found 28/8$814

Fri 3/1009:10SYD - ORD

1 stop24h 04mMultiple Airlines

Deal found 27/8$930

Wed 15/1016:40SYD - ORD

1 stop32h 05mEtihad Airways

Deal found 28/8$953

Wed 10/1210:40SYD - MDW

2 stops24h 56mDelta

Deal found 27/8$1,315

Fri 3/1017:45SYD - MDW

3 stops53h 54mMultiple Airlines

Deal found 27/8$1,404

Mon 9/217:45SYD - MDW

3 stops38h 35mMultiple Airlines

Deal found 26/8$1,406

Sun 7/1210:40SYD - MDW

2 stops24h 27mDelta

Deal found 27/8$1,412

Sun 7/1221:40SYD - MDW

3 stops32h 30mMultiple Airlines

Deal found 27/8$1,596

Fly from

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 2/10

09:20-16:42

1 stop22h 22m

Chicago O'Hare Intl

Fri 10/10

15:45-08:20

1 stop24h 35m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 3/10

09:20-15:00

1 stop20h 40m

Chicago O'Hare Intl

Wed 8/10

15:45-08:20

1 stop24h 35m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 1/10

09:20-16:42

1 stop22h 22m

Chicago O'Hare Intl

Fri 10/10

15:45-08:20

1 stop24h 35m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sun 28/9

09:20-16:51

2 stops22h 31m

Chicago O'Hare Intl

Wed 8/10

15:45-08:20

1 stop24h 35m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 29/9

09:20-15:00

1 stop20h 40m

Chicago O'Hare Intl

Fri 10/10

15:45-08:20

1 stop24h 35m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 30/9

09:20-15:00

1 stop20h 40m

Chicago O'Hare Intl

Fri 10/10

15:45-08:20

1 stop24h 35m

$1,481

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 4/10

09:20-16:51

2 stops22h 31m

Chicago O'Hare Intl

Sat 11/10

13:27-08:20

2 stops26h 53m

$1,505

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 27/11

10:40-16:39

2 stops22h 59m

Chicago Midway

Mon 8/12

09:30-08:30

2 stops30h 00m

$2,063

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 20/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Mon 27/10

13:48-07:30

2 stops25h 42m

$2,063

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Wed 12/11

10:47-08:30

2 stops28h 43m

$2,360

Flights are sorted by cheapest return flights first.

Deals found on 28/8

Showing 1-10 of 29 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?

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

How long is the flight to Chicago?

On average, a flight from Sydney to Chicago takes 22 hours 20 minutes. Flights to Chicago from other popular cities in Australia 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 Monday at midday, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday evenings, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Sydney to Chicago are Qantas Airways, Air Canada and United Airlines.

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Sydney to Chicago are Qantas Airways, American Airlines and Air Canada.

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

Get a feel of what it's like to fly with ANA, Air New Zealand, andQantas Airways to the United States by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

ANA

8.4

Very Good

941 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

ANA ground and flight crew are the best their is They are now officially my Airline of choice Crew are very attentive, friendly, sincere, helpful and respond to queries accurately, promptly and gives you the peace of mind when travelling Salute to the World’s Best Airline for me

ANA

8.4

Very Good

941 reviews

ANA

8.4

Very Good

941 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Air New Zealand

8.0

Very Good

505 reviews

ANA

8.4

Very Good

941 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Qantas Airways

7.5

Good

905 reviews

ANA

8.4

Very Good

941 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

United Airlines

7.4

Good

8,941 reviews

ANA

8.4

Very Good

941 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

Air Canada

7.1

Good

10,000 reviews

ANA

8.4

Very Good

941 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

Anonymous,Aug 2025

SFO - NRT

FAQs about flying to Chicago

Getting around Chicago

Chicago’s regular, grid-like layout makes navigation straightforward, but the “City With Big Shoulders” can be a little too large to get around easily on foot. Fortunately, the city’s public transportation system, including the famous “L” (short for “elevated train tracks”), is efficient, with especially good coverage in the city centre area. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Cycling is a popular way to get around and with all of Chicago’s lakefront property, it can be a great way to enjoy the city.

Getting downtown from the airport

Chicago’s major airport is O’Hare International Airport (ORD) located in the city’s northwest corner, about 27 km away from the Loop. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available.

Travel Tips

One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water.

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, Qantas Airways 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 $50, while return flights cost around $177.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around $134, however they can be found for as little as $115.
Where does the fastest flight to Chicago depart from?
For those looking to save time traveling to Chicago, Sydney Kingsford Smith offers the quickest one-way flight (21 hours 41 minutes).
Which airport is closest to River North?
f being close to River North is important to you, you’ll want to land at Chicago O'Hare Intl Airport.
Does Chicago O'Hare Intl have car hire?
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?

Cheapflights makes it easy to find Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Cheapflights helps you find that perfect flight to Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights to Chicago with no change fees?

Certainly. Search results for flights to Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Of course! You can track prices for flights to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals to set up your price alerts.

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$681+ 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 647,157 searches and data was last updated on 29 August 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 29 August 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 29 August 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 Sydney to Chicago. Price data was last updated on 22 August 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 Sydney to Chicago. Price data was last updated on 13 October 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

Get a feel of what it's like to fly with ANA, Air New Zealand, andQantas Airways to the United States by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

FAQs about flying to Chicago

Getting around Chicago

Getting downtown from the airport

Travel Tips

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?

Which airport is closest to River North?

Does Chicago O'Hare Intl have car hire?

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.

Find the best flight deals to Chicago

Some of the lowest fares we’ve come across for flights to Chicago.

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 29 August 2025.