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$704+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
15 May — 22 May1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

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 15 April 2026.

Fri 1/513:15
SYD
-
ORD
2 stops31h 35m
Multiple Airlines
Sat 16/506:55
ORD
-
SYD
3 stops48h 15m
Multiple Airlines
Deal found 11/4$1,500
Sat 9/513:15
SYD
-
ORD
2 stops31h 44m
Multiple Airlines
Sun 31/507:15
ORD
-
SYD
2 stops37h 35m
Multiple Airlines
Deal found 14/4$1,536
Wed 27/513:15
SYD
-
ORD
3 stops46h 17m
Multiple Airlines
Wed 3/606:55
ORD
-
SYD
3 stops37h 55m
Multiple Airlines
Deal found 11/4$1,548
Fri 1/513:15
SYD
-
MDW
3 stops41h 58m
Multiple Airlines
Sat 16/506:00
MDW
-
SYD
3 stops49h 10m
Multiple Airlines
Deal found 12/4$1,580
Tue 8/911:45
SYD
-
ORD
2 stops32h 00m
ANA
Fri 11/917:45
ORD
-
SYD
1 stop34h 25m
ANA
Deal found 14/4$1,607
Thu 30/713:15
SYD
-
ORD
3 stops46h 38m
Multiple Airlines
Sat 1/809:33
ORD
-
SYD
3 stops35h 17m
Multiple Airlines
Deal found 11/4$1,612
Wed 11/1112:25
SYD
-
ORD
1 stop35h 55m
ANA
Mon 16/1120:00
ORD
-
SYD
2 stops31h 15m
ANA
Deal found 13/4$1,633
Thu 8/1012:45
SYD
-
ORD
2 stops32h 20m
ANA
Thu 22/1017:45
ORD
-
SYD
1 stop34h 25m
ANA
Deal found 12/4$1,650
Mon 11/513:15
SYD
-
ORD
3 stops46h 17m
Multiple Airlines
Mon 18/508:30
ORD
-
SYD
3 stops36h 35m
Multiple Airlines
Deal found 11/4$1,674
Wed 3/617:50
SYD
-
ORD
1 stop27h 14m
Multiple Airlines
Tue 23/621:13
ORD
-
SYD
1 stop43h 17m
Multiple Airlines
Deal found 14/4$1,688
Tue 5/517:50
SYD
-
MDW
2 stops32h 19m
Multiple Airlines
Wed 20/506:00
MDW
-
SYD
2 stops34h 30m
Multiple Airlines
Deal found 15/4$1,711
Wed 27/517:50
SYD
-
MDW
2 stops32h 22m
Multiple Airlines
Wed 3/606:00
MDW
-
SYD
2 stops34h 30m
Multiple Airlines
Deal found 11/4$1,834

Find flight deals to Chicago

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 15 April 2026.

Return from

$1,500

One-way from

$839

Popular in

April

Cheapest in

August

Average price

$2,238
1/5-16/5
  • 1/5-16/5
  • 5 total stops
  • 79h 50m total
  • Sydney to Chicago
Search Deals
18/6
  • 18/6
  • 3 total stops
  • 48h 05m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($143 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 April 2026
Search Deals

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 15 April 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 5/5

17:50-11:09

2 stops32h 19m

Chicago Midway

Wed 20/5

06:00-07:30

2 stops34h 30m

$1,711

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 24/7

13:15-06:19

2 stops32h 04m

Chicago O'Hare Intl

Tue 28/7

06:55-22:10

3 stops48h 15m

$1,825

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 16/5

15:40-14:20

2 stops37h 40m

Chicago O'Hare Intl

Sat 6/6

14:00-16:50

1 stop35h 50m

$2,107

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 1/10

09:20-20:12

2 stops25h 52m

Chicago O'Hare Intl

Fri 9/10

15:40-08:20

1 stop24h 40m

$2,184

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 29/4

13:15-23:59

2 stops25h 44m

Chicago O'Hare Intl

Sat 2/5

18:56-11:50

2 stops25h 54m

$2,231

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 7/5

20:45-13:13

3 stops31h 28m

Chicago O'Hare Intl

Wed 20/5

17:44-18:50

2 stops34h 06m

$2,236

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 25/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Mon 1/6

12:53-06:50

2 stops26h 57m

$2,354

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 7/5

09:15-18:33

2 stops24h 18m

Chicago Midway

Wed 20/5

10:59-06:50

2 stops28h 51m

$2,356

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/6

09:15-21:09

2 stops26h 54m

Chicago Midway

Thu 2/7

13:49-06:50

2 stops26h 01m

$2,416

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/6

09:15-08:37

2 stops38h 22m

Chicago Midway

Tue 18/8

13:05-06:50

2 stops26h 45m

$2,429

Flights are sorted by cheapest return flights first.

Deals found on 14/4

Showing 1-10 of 38 resultsSorted by cheapest first
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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 10 April 2026.

Booking 72 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 24 hours 30 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 $949
Air Canada
Air Canada
From $1,065
United Airlines
United Airlines
From $1,390
Air New Zealand
Air New Zealand
From $1,079

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.

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 15 April 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
1,173 reviews
Check prices

Crew

8.7

Food

7.8

Entertainment

8.0

Comfort

8.2

Boarding

8.6

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
ANA
8.4
Very Good
1,173 reviews
ANA
8.4
Very Good
1,173 reviews
Check prices

Crew

8.7

Food

7.8

Entertainment

8.0

Comfort

8.2

Boarding

8.6

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
Air New Zealand
8.0
Very Good
627 reviews
ANA
8.4
Very Good
1,173 reviews
Check prices

Crew

8.7

Food

7.8

Entertainment

8.0

Comfort

8.2

Boarding

8.6

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
Qantas Airways
7.5
Good
1,019 reviews
ANA
8.4
Very Good
1,173 reviews
Check prices

Crew

8.7

Food

7.8

Entertainment

8.0

Comfort

8.2

Boarding

8.6

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
United Airlines
7.4
Good
9,592 reviews
ANA
8.4
Very Good
1,173 reviews
Check prices

Crew

8.7

Food

7.8

Entertainment

8.0

Comfort

8.2

Boarding

8.6

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.
Air Canada
7.1
Good
10,930 reviews
ANA
8.4
Very Good
1,173 reviews
Check prices

Crew

8.7

Food

7.8

Entertainment

8.0

Comfort

8.2

Boarding

8.6

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Alejandro,Apr 2026

SFO - HND

Food was good, not exceptional. On my second flight, Tokyo to Hiroshima, a single cup of coffee was offered, not a bag of pretzels or cookies. Granted, the flight was only an hour and a half, but this seems stingy.

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 $118, while return flights cost around $182.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $409, however they can be found for as little as $182.

  • 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 (22 hours 45 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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