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 New Zealand 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 $156, while return flights cost around $216.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around $412, however they can be found for as little as $216.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Brisbane offers the quickest one-way flight (19 hours 50 minutes).

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).

$633+ Cheap Flights to Chicago, Illinois

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

Cheapest

Best

Last-minute

One-way

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 3 October 2026.

Thu 5/1111:10 -

1 stop23h 49m

Mon 9/1110:32 -

1 stop29h 28m

Deal found 1/10$1,058

Tue 10/1111:10 -

1 stop21h 55m

Mon 23/1112:57 -

2 stops27h 03m

Deal found 30/9$1,062

Mon 5/1010:15 -

2 stops22h 44m

Mon 19/1013:25 -

2 stops26h 25m

Deal found 2/10$1,065

Mon 9/1111:10 -

1 stop22h 50m

Wed 25/1118:45 -

1 stop21h 15m

Deal found 30/9$1,067

Mon 19/1010:10 -

1 stop25h 50m

Tue 3/1113:24 -

1 stop26h 36m

Deal found 29/9$1,070

Mon 5/1010:10 -

1 stop24h 28m

Mon 19/1012:00 -

1 stop28h 05m

Deal found 30/9$1,083

Wed 14/1010:10 -

1 stop22h 41m

Thu 29/1017:53 -

1 stop23h 07m

Deal found 2/10$1,129

Sat 7/1111:10 -

1 stop25h 49m

Sat 21/1122:03 -

1 stop41h 57m

Deal found 30/9$1,133

Sat 7/1111:10 -

1 stop23h 49m

Wed 25/1117:09 -

1 stop22h 51m

Deal found 30/9$1,137

Wed 7/1010:10 -

1 stop21h 49m

Thu 12/1111:45 -

1 stop28h 15m

Deal found 2/10$1,146

Fri 23/1010:10 -

1 stop24h 28m

Thu 29/1018:55 -

1 stop22h 05m

Deal found 2/10$1,199

Find flight deals to Chicago

Return from	$1,058
One-way from	$633
Popular in	May
Cheapest in	October
Average price	$1,486

American Airlines
5/11-9/11
2 total stops
53h 17m total
Sydney to Chicago

Search Deals

Qantas Airways
3/12-31/12
1 total stop
22h 49m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($164 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($50 potential savings vs. average return price).

Search Deals

Average for return flights in October 2026

Search Deals

Fly from

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sat 7/11

10:40-15:45

1 stop22h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$708

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 17/11

10:40-20:49

2 stops27h 09m

Chicago O'Hare Intl

Tue 24/11

14:32-08:30

1 stop24h 58m

$1,067

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 11/12

21:40-13:15

2 stops32h 35m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,458

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 2/12

15:15-12:30

2 stops62h 15m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,486

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 3/12

10:40-13:33

1 stop19h 53m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,561

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sat 7/11

21:40-13:09

3 stops32h 29m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,564

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 14/12

14:00-05:37

3 stops32h 37m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,638

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sun 6/12

10:40-13:33

1 stop43h 53m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,646

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Fri 4/12

10:40-17:15

1 stop23h 35m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,659

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 14/12

21:10-14:30

1 stop34h 20m

Chicago O'Hare Intl

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,674

Flights are sorted by cheapest return flights first.

Deals found on 3/10

Showing 1-10 of 22 resultsSorted by cheapest first

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.

SYD-CHI

SYD-ORD

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

SYD-CHI

SYD-ORD

How long is the flight to Chicago?

On average, a flight from Sydney to Chicago takes 24 hours 24 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.

What are the most popular airlines that fly to Chicago?

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

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Sydney to Chicago are Air Canada, American Airlines 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).

When is the best time to book a flight to Chicago?

Booking 85 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.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Air New Zealand,Qantas Airways, andUnited Airlines 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.

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Air New Zealand

8.0

Very Good

669 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Qantas Airways

7.5

Good

1,102 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

United Airlines

7.4

Good

10,287 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

Air Canada

7.1

Good

11,718 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

American Airlines

7.0

Good

12,130 reviews

Air New Zealand

8.0

Very Good

669 reviews

Check prices

Reviews

1 / 20

6.0

Good

Anonymous,Aug 2026

FLL - IAH

All good. Problem was delay caused by weather in Houston creating anxiety about my AirNZ connection. Nothing that United could do about that, and in fairness th captain kept us very well informed

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, Air New Zealand 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 $156, while return flights cost around $216.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around $412, however they can be found for as little as $216.
Where does the fastest flight to Chicago depart from?
For those looking to save time traveling to Chicago, Brisbane offers the quickest one-way flight (19 hours 50 minutes).
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

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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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$633+ Cheap flights to Chicago

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/12. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2026

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 3 October 2026.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 3 October 2026.

Best flights to ChicagoDiscover 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 3 October 2026.

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 3 October 2026.

Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated 3 October 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 3 October 2026 and is based on user searches.

One-way flights to ChicagoSearch for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 3 October 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 3 October 2026.

Find flight deals to Chicago

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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

How long is the flight to Chicago?

On average, a flight from Sydney to Chicago takes 24 hours 24 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.

What are the most popular airlines that fly to Chicago?

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

What are the cheapest airlines that fly to Chicago?

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals 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

Plan your trip to Chicago by taking into account the average temperature totals by month.

When is the best time to book a flight to Chicago?

Booking 85 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.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Air New Zealand,Qantas Airways, andUnited Airlines 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?

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.

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

Airports serving Chicago

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

Other flight destinations closest to Chicago

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Complete your trip

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Most traveled routes by our users

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How does Cheapflights help users find flights to Chicago?

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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 3 October 2026.

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 3 October 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 3 October 2026 and is based on user searches.

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 3 October 2026.