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, American Airlines 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 $106, while return flights cost around $212.

How much is a return flight to Chicago?

A return flight to Chicago will typically cost around $404, however they can be found for as little as $212.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Melbourne offers the quickest one-way flight (20 hours 41 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).

$838+ 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 20 August 2026.

Tue 8/913:15 -

2 stops32h 02m

Tue 22/906:30 -

3 stops48h 55m

Deal found 16/8$1,159

Fri 9/1014:15 -

3 stops31h 01m

Sun 25/1006:30 -

3 stops38h 05m

Deal found 20/8$1,393

Thu 3/909:30 -

2 stops48h 32m

Wed 16/906:30 -

2 stops33h 30m

Deal found 18/8$1,531

Mon 31/806:25 -

2 stops24h 29m

Tue 15/921:10 -

2 stops57h 05m

Deal found 16/8$1,719

Tue 8/909:55 -

2 stops28h 10m

Tue 22/916:00 -

2 stops25h 45m

Deal found 16/8$1,731

Wed 4/1111:50 -

2 stops26h 59m

Mon 9/1110:34 -

2 stops31h 01m

Deal found 18/8$1,753

Sun 30/809:30 -

1 stop35h 29m

Tue 15/906:30 -

2 stops33h 30m

Deal found 19/8$1,778

Sun 30/809:30 -

2 stops40h 25m

Tue 15/906:25 -

2 stops33h 35m

Deal found 19/8$1,800

Mon 2/1110:40 -

2 stops23h 07m

Wed 11/1113:22 -

2 stops26h 08m

Deal found 18/8$2,450

Fri 9/1010:15 -

2 stops23h 45m

Sun 25/1010:01 -

2 stops29h 29m

Deal found 20/8$2,520

Wed 25/1110:40 -

2 stops29h 16m

Sat 9/113:00 -

2 stops26h 30m

Deal found 19/8$2,647

Wed 4/1110:40 -

2 stops24h 20m

Mon 9/1113:22 -

2 stops26h 08m

Deal found 18/8$2,678

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 20 August 2026.

Thu 5/1115:15 -

1 stop38h 40m

Mon 9/1114:35 -

1 stop37h 15m

Deal found 19/8$2,156

Tue 8/909:55 -

2 stops26h 40m

Tue 22/917:53 -

2 stops23h 52m

Deal found 15/8$2,168

Tue 8/910:10 -

1 stop43h 10m

Tue 22/916:15 -

2 stops33h 10m

Deal found 15/8$2,174

Mon 7/910:20 -

1 stop21h 16m

Tue 22/915:56 -

2 stops24h 04m

Deal found 16/8$2,260

Wed 4/1110:40 -

2 stops23h 07m

Wed 11/1113:22 -

2 stops26h 08m

Deal found 18/8$2,450

Thu 1/1010:10 -

1 stop42h 45m

Thu 8/1016:15 -

2 stops34h 20m

Deal found 17/8$2,174

Tue 29/906:00 -

2 stops46h 55m

Tue 6/1016:15 -

1 stop28h 30m

Deal found 15/8$2,248

Tue 3/1111:50 -

2 stops22h 15m

Mon 9/1121:35 -

1 stop40h 25m

Deal found 19/8$2,263

Wed 25/1118:30 -

2 stops35h 25m

Tue 29/1214:35 -

1 stop47h 40m

Deal found 19/8$2,198

Fri 9/1010:15 -

2 stops23h 45m

Sun 25/1010:01 -

2 stops29h 29m

Deal found 20/8$2,520

Thu 3/919:45 -

2 stops33h 35m

Wed 16/916:15 -

1 stop36h 55m

Deal found 16/8$2,244

Wed 4/1110:40 -

2 stops24h 20m

Mon 9/1113:22 -

2 stops26h 08m

Deal found 18/8$2,678

Thu 5/1110:40 -

2 stops23h 07m

Tue 10/1113:22 -

2 stops26h 08m

Deal found 18/8$2,682

Fri 25/909:15 -

2 stops24h 04m

Sun 4/1013:19 -

2 stops26h 31m

Deal found 15/8$2,812

Sat 3/1009:15 -

2 stops23h 44m

Sat 10/1013:27 -

2 stops26h 23m

Deal found 19/8$2,849

Mon 7/909:15 -

2 stops23h 46m

Tue 22/913:00 -

2 stops26h 50m

Deal found 15/8$2,888

Tue 8/909:15 -

2 stops24h 04m

Tue 22/913:19 -

2 stops26h 31m

Deal found 15/8$2,888

Thu 3/909:15 -

2 stops24h 18m

Wed 16/913:00 -

2 stops26h 50m

Deal found 16/8$2,892

Find flight deals to Chicago

Return from	$1,159
One-way from	$838
Popular in	July
Cheapest in	October
Average price	$1,617

8/9-22/9
5 total stops
80h 57m total
Sydney to Chicago

Search Deals

21/10
3 total stops
50h 19m total
Sydney to Chicago

Search Deals

Highest demand for flights based on searches. 4% potential increase in price ($78 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($24 potential savings vs. average return price).

Search Deals

Average for return flights in August 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

Thu 5/11

15:15-12:55

1 stop38h 40m

Chicago O'Hare Intl

Mon 9/11

14:35-20:50

1 stop37h 15m

$2,156

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

09:55-21:35

2 stops26h 40m

Chicago O'Hare Intl

Tue 22/9

17:53-08:45

2 stops23h 52m

$2,168

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 8/9

10:10-14:20

1 stop43h 10m

Chicago O'Hare Intl

Tue 22/9

16:15-16:25

2 stops33h 10m

$2,174

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 1/10

10:10-13:55

1 stop42h 45m

Chicago O'Hare Intl

Thu 8/10

16:15-18:35

2 stops34h 20m

$2,174

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 25/11

18:30-12:55

2 stops35h 25m

Chicago O'Hare Intl

Tue 29/12

14:35-07:15

1 stop47h 40m

$2,198

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 3/9

19:45-14:20

2 stops33h 35m

Chicago O'Hare Intl

Wed 16/9

16:15-20:10

1 stop36h 55m

$2,244

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 29/9

06:00-13:55

2 stops46h 55m

Chicago O'Hare Intl

Tue 6/10

16:15-12:45

1 stop28h 30m

$2,248

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 7/9

10:20-16:36

1 stop21h 16m

Chicago O'Hare Intl

Tue 22/9

15:56-07:00

2 stops24h 04m

$2,260

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 3/11

11:50-17:05

2 stops22h 15m

Chicago O'Hare Intl

Mon 9/11

21:35-07:00

1 stop40h 25m

$2,263

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 4/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Wed 11/11

13:22-08:30

2 stops26h 08m

$2,450

Flights are sorted by cheapest return flights first.

Deals found on 15/8

Showing 1-10 of 33 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

SYD-MDW

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

SYD-MDW

How long is the flight to Chicago?

On average, a flight from Sydney to Chicago takes 25 hours 0 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 Canada and United Airlines.

What are the cheapest airlines that fly to Chicago?

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

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

662 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

Air New Zealand

8.0

Very Good

662 reviews

Air New Zealand

8.0

Very Good

662 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

Qantas Airways

7.5

Good

1,083 reviews

Air New Zealand

8.0

Very Good

662 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

United Airlines

7.4

Good

10,101 reviews

Air New Zealand

8.0

Very Good

662 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

American Airlines

7.1

Good

11,969 reviews

Air New Zealand

8.0

Very Good

662 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

Air Canada

7.1

Good

11,506 reviews

Air New Zealand

8.0

Very Good

662 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Viren,June 2026

MEL - LAX

Flight got delayed and made us take a transit visa which was not a told before hand.

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, American Airlines 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 $106, while return flights cost around $212.
How much is a return flight to Chicago?
A return flight to Chicago will typically cost around $404, however they can be found for as little as $212.
Where does the fastest flight to Chicago depart from?
For those looking to save time traveling to Chicago, Melbourne offers the quickest one-way flight (20 hours 41 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

Browse thousands of different options on Cheapflights for your next trip

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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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$838+ 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 21/10. 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 20 August 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 20 August 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 20 August 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 20 August 2026.

Last-minute flights to ChicagoDiscover last-minute flight deals to Chicago. Data last updated 20 August 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 20 August 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 20 August 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 20 August 2026.

Find flight deals to Chicago

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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

How long is the flight to Chicago?

On average, a flight from Sydney to Chicago takes 25 hours 0 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 Canada and United Airlines.

What are the cheapest airlines that fly to Chicago?

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

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.

Find the best flight deals to Chicago

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

Airports serving Chicago

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Search flights to Chicago by cabin class

Find flights to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Find the best flight deals from Chicago

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

Reserve a car hire and hotel room to complete your trip to Chicago.

Most traveled routes by our users

Browse our most popular destinations

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Popular United States flight routes

Browse through the most popular flight routes to the United States at this time.

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Fly with Cheapflights

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 20 August 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 20 August 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 20 August 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 20 August 2026.