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$832+ 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 27/2. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
13 Feb — 20 Feb1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Find the latest flights to Chicago in 2026, 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 14 January 2026.

Return from

$1,503

One-way from

$832

Popular in

December

Cheapest in

February

Average price

$1,479
Air New Zealand
  • Air New Zealand
  • 1/2-16/2
  • 4 total stops
  • 56h 54m total
  • Sydney to Chicago
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27/2
  • 27/2
  • 3 total stops
  • 34h 54m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($305 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($53 potential savings vs. average return price).
Search Deals
Average for return flights in January 2026
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Find flight deals to Chicago

Enter your travel dates to find the best prices.

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 14 January 2026.

Sun 1/209:55
SYD
-
ORD
2 stops30h 04m
Air New Zealand
Mon 16/212:55
ORD
-
SYD
2 stops26h 50m
Air New Zealand
Deal found 12/1$1,503
Thu 29/111:20
SYD
-
ORD
2 stops37h 45m
Air Canada
Wed 11/215:35
ORD
-
SYD
1 stop25h 00m
Air Canada
Deal found 12/1$1,523
Thu 26/211:20
SYD
-
ORD
1 stop22h 18m
Air Canada
Thu 5/315:35
ORD
-
SYD
1 stop25h 00m
Air Canada
Deal found 12/1$1,565
Mon 20/411:55
SYD
-
ORD
2 stops26h 33m
Air New Zealand
Mon 27/415:45
ORD
-
SYD
2 stops26h 00m
Air New Zealand
Deal found 13/1$1,577
Mon 2/211:20
SYD
-
ORD
1 stop20h 21m
Air Canada
Tue 17/207:15
ORD
-
SYD
2 stops33h 20m
Air Canada
Deal found 13/1$1,580
Wed 18/211:20
SYD
-
ORD
2 stops22h 25m
Air Canada
Sun 1/320:40
ORD
-
SYD
2 stops43h 55m
Air Canada
Deal found 12/1$1,590
Tue 4/809:15
SYD
-
MDW
2 stops23h 50m
Delta
Tue 18/814:00
MDW
-
SYD
2 stops25h 35m
Delta
Deal found 11/1$2,069
Fri 12/609:15
SYD
-
MDW
2 stops24h 16m
Delta
Sun 12/714:00
MDW
-
SYD
2 stops25h 35m
Delta
Deal found 11/1$2,295
Wed 18/210:40
SYD
-
MDW
2 stops24h 05m
Delta
Sun 1/312:45
MDW
-
SYD
2 stops25h 05m
Delta
Deal found 12/1$2,375
Mon 16/210:40
SYD
-
MDW
2 stops25h 00m
Delta
Sat 28/213:28
MDW
-
SYD
2 stops26h 02m
Delta
Deal found 12/1$2,444
Thu 29/110:40
SYD
-
MDW
2 stops24h 15m
Delta
Wed 11/209:33
MDW
-
SYD
2 stops29h 57m
Delta
Deal found 12/1$2,519
Tue 6/1010:15
SYD
-
MDW
2 stops24h 22m
Delta
Mon 12/1013:00
MDW
-
SYD
2 stops26h 35m
Delta
Deal found 14/1$2,522

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 647,157 searches and data was last updated on 14 January 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Sydney

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 29/1

11:20-08:05

2 stops37h 45m

Chicago O'Hare Intl

Wed 11/2

15:35-09:35

1 stop25h 00m

$1,523

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 26/2

11:20-16:45

2 stops22h 25m

Chicago O'Hare Intl

Thu 5/3

15:35-09:35

1 stop25h 00m

$1,565

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 18/2

11:20-14:41

1 stop20h 21m

Chicago O'Hare Intl

Sun 22/2

20:40-09:35

2 stops43h 55m

$1,683

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 18/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Sun 1/3

12:45-06:50

2 stops25h 05m

$2,375

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 16/2

10:40-18:40

2 stops25h 00m

Chicago Midway

Sat 28/2

13:28-08:30

2 stops26h 02m

$2,444

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 26/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Thu 5/3

13:49-08:30

2 stops25h 41m

$2,444

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 29/1

10:40-17:55

2 stops24h 15m

Chicago Midway

Wed 11/2

09:33-08:30

2 stops29h 57m

$2,526

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 27/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Fri 6/3

13:29-08:30

2 stops26h 01m

$2,526

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 1/2

10:40-17:29

2 stops23h 49m

Chicago Midway

Mon 16/2

13:26-08:30

2 stops26h 04m

$2,601

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 22/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Sun 19/7

13:00-06:35

2 stops26h 35m

$2,822

Flights are sorted by cheapest return flights first.

Deals found on 13/1

Showing 1-10 of 34 results
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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.
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?

Use this chart to determine the optimal time to book a return flight from Sydney to Chicago. Price data was last updated on 9 January 2026.

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 6 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.

Qantas Airways
Qantas Airways
From $946
Air Canada
Air Canada
From $1,167
United Airlines
United Airlines
From $1,476
Air New Zealand
Air New Zealand
From $1,146

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

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.

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 insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 14 January 2026.
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
1,069 reviews
Check prices

Boarding

8.5

Overall

8.4

Crew

8.7

Food

7.7

Entertainment

7.9

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Lindsey,Jan 2026

CGK - HND

All of the flight attendants were very nice & attentive. The bathrooms were kept very clean. We have no complaints!
ANA
8.4
Very Good
1,069 reviews
ANA
8.4
Very Good
1,069 reviews
Check prices

Boarding

8.5

Overall

8.4

Crew

8.7

Food

7.7

Entertainment

7.9

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Lindsey,Jan 2026

CGK - HND

All of the flight attendants were very nice & attentive. The bathrooms were kept very clean. We have no complaints!
Air New Zealand
8.0
Very Good
570 reviews
ANA
8.4
Very Good
1,069 reviews
Check prices

Boarding

8.5

Overall

8.4

Crew

8.7

Food

7.7

Entertainment

7.9

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Lindsey,Jan 2026

CGK - HND

All of the flight attendants were very nice & attentive. The bathrooms were kept very clean. We have no complaints!
Qantas Airways
7.5
Good
970 reviews
ANA
8.4
Very Good
1,069 reviews
Check prices

Boarding

8.5

Overall

8.4

Crew

8.7

Food

7.7

Entertainment

7.9

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Lindsey,Jan 2026

CGK - HND

All of the flight attendants were very nice & attentive. The bathrooms were kept very clean. We have no complaints!
United Airlines
7.4
Good
9,154 reviews
ANA
8.4
Very Good
1,069 reviews
Check prices

Boarding

8.5

Overall

8.4

Crew

8.7

Food

7.7

Entertainment

7.9

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Lindsey,Jan 2026

CGK - HND

All of the flight attendants were very nice & attentive. The bathrooms were kept very clean. We have no complaints!
Air Canada
7.1
Good
10,619 reviews
ANA
8.4
Very Good
1,069 reviews
Check prices

Boarding

8.5

Overall

8.4

Crew

8.7

Food

7.7

Entertainment

7.9

Comfort

8.2

Reviews

1 / 20
10.0
Excellent

Lindsey,Jan 2026

CGK - HND

All of the flight attendants were very nice & attentive. The bathrooms were kept very clean. We have no complaints!

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 $49, while return flights cost around $714.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $1,154, however they can be found for as little as $714.

  • 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 (20 hours 7 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

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Airports serving Chicago

Book a flight to or from one of these Chicago airports.
Flights to Midway
Flights to O'Hare Intl
Flights from Midway
Flights from O'Hare Intl

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