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$701+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
29 janv. — 5 févr.1
1 adult

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 24 janvier 2025.

Return from

$1,122

One-way from

$701

Popular in

December

Cheapest in

March

Average price

$1,945
Qantas Airways
  • Qantas Airways
  • 10/2-17/2
  • 2 total stops
  • 47h 31m total
  • Sydney to Chicago
Qantas Airways
  • Qantas Airways
  • 1/6
  • 1 total stop
  • 23h 05m total
  • Sydney to Chicago
Highest demand for flights based on searches. 10% potential increase in price ($343 potential increase over avg. return price).
Cheapest flight prices on average. 3% potential price decrease ($90 potential savings vs. average return price).
Average for return flights in January 2025

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 24 janvier 2025.

lun. 10/211:15SYD - ORD
1 stop21h 44mQantas Airways
lun. 17/214:13ORD - SYD
1 stop25h 47mQantas Airways
Deal found 23/1$1,122
sam. 25/111:15SYD - ORD
1 stop19h 34mMultiple Airlines
sam. 8/217:40ORD - SYD
1 stop22h 20mMultiple Airlines
Deal found 23/1$1,177
mar. 28/1021:45SYD - ORD
2 stops47h 18mANA
lun. 1/1216:25ORD - SYD
1 stop34h 50mANA
Deal found 22/1$1,746
mer. 5/311:20SYD - ORD
2 stops25h 35mAir Canada
mar. 25/307:20ORD - SYD
2 stops33h 15mAir Canada
Deal found 23/1$1,749
mer. 30/709:30SYD - ORD
2 stops22h 20mUnited Airlines
sam. 23/821:21ORD - SYD
1 stop42h 34mUnited Airlines
Deal found 22/1$2,095
mar. 7/1022:05SYD - ORD
2 stops39h 55mTurkish Airlines
mer. 5/1111:55ORD - SYD
2 stops38h 40mTurkish Airlines
Deal found 23/1$2,097
mar. 8/709:25SYD - ORD
2 stops38h 06mDelta
mar. 29/709:30ORD - SYD
2 stops30h 05mDelta
Deal found 23/1$2,108
lun. 7/709:10SYD - ORD
1 stop19h 50mAmerican Airlines
lun. 28/714:00ORD - SYD
2 stops26h 05mAmerican Airlines
Deal found 23/1$2,220
ven. 14/310:05SYD - MDW
2 stops23h 57mDelta
sam. 22/313:12MDW - SYD
2 stops26h 33mDelta
Deal found 22/1$2,259
mar. 8/710:05SYD - ORD
1 stop43h 20mCathay Pacific
mar. 29/716:05ORD - SYD
2 stops34h 35mCathay Pacific
Deal found 23/1$2,328
jeu. 31/708:15SYD - ORD
2 stops50h 20mJapan Airlines
sam. 23/801:30ORD - SYD
1 stop37h 40mJapan Airlines
Deal found 23/1$2,541
mar. 11/207:55SYD - MDW
3 stops45h 15mMultiple Airlines
lun. 17/219:55MDW - SYD
3 stops47h 35mMultiple Airlines
Deal found 23/1$3,190

Find flights to Chicago within your budget

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 24 janvier 2025.

Fly from

Any airport

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

lun. 10/2

11:15-15:59

1 stop21h 44m

Chicago O'Hare Intl

lun. 17/2

14:13-09:00

1 stop25h 47m

$1,122

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mer. 12/2

14:00-05:28

2 stops32h 28m

Chicago O'Hare Intl

mer. 19/2

11:35-12:30

2 stops31h 55m

$1,402

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mer. 5/3

11:20-19:55

2 stops25h 35m

Chicago O'Hare Intl

mar. 25/3

07:20-08:35

2 stops33h 15m

$1,749

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mar. 8/7

09:25-08:31

2 stops38h 06m

Chicago O'Hare Intl

mar. 29/7

09:30-06:35

2 stops30h 05m

$2,108

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

lun. 7/7

09:10-14:00

1 stop19h 50m

Chicago O'Hare Intl

lun. 28/7

14:00-07:05

2 stops26h 05m

$2,220

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

ven. 14/3

10:05-18:02

2 stops23h 57m

Chicago Midway

sam. 22/3

13:12-07:45

2 stops26h 33m

$2,259

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

mar. 8/7

10:05-14:25

1 stop43h 20m

Chicago O'Hare Intl

mar. 29/7

16:05-17:40

2 stops34h 35m

$2,328

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

sam. 5/7

10:20-23:50

2 stops28h 30m

Chicago O'Hare Intl

ven. 25/7

15:51-06:55

2 stops24h 04m

$2,545

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mar. 11/2

07:55-12:10

3 stops45h 15m

Chicago Midway

lun. 17/2

19:55-12:30

3 stops47h 35m

$3,190

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

dim. 1/6

09:10-17:15

1 stop23h 05m

$701

Flights are sorted by cheapest return flights first.

Deals found on 23/1

Showing 1-10 of 19 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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 17 January 2025.

Booking 37 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 5 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?

Use this chart to determine the cheapest time to fly return from Sydney to Chicago. Price data was last updated on 13 October 2024.

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 cheapest airlines that fly to Chicago?

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

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 24 janvier 2025.
8.8
Very Good
62 reviews

Crew

9.1

Comfort

8.1

Food

7.8

Overall

8.8

Entertainment

7.3

Boarding

8.7

Reviews

1 / 2

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

8.8
Very Good
62 reviews
8.8
Very Good
62 reviews

Crew

9.1

Comfort

8.1

Food

7.8

Overall

8.8

Entertainment

7.3

Boarding

8.7

Reviews

1 / 2

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

8.5
Very Good
1,037 reviews
8.8
Very Good
62 reviews

Crew

9.1

Comfort

8.1

Food

7.8

Overall

8.8

Entertainment

7.3

Boarding

8.7

Reviews

1 / 2

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

8.3
Very Good
1,446 reviews
8.8
Very Good
62 reviews

Crew

9.1

Comfort

8.1

Food

7.8

Overall

8.8

Entertainment

7.3

Boarding

8.7

Reviews

1 / 2

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

8.1
Very Good
188 reviews
8.8
Very Good
62 reviews

Crew

9.1

Comfort

8.1

Food

7.8

Overall

8.8

Entertainment

7.3

Boarding

8.7

Reviews

1 / 2

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

8.0
Very Good
8,502 reviews
8.8
Very Good
62 reviews

Crew

9.1

Comfort

8.1

Food

7.8

Overall

8.8

Entertainment

7.3

Boarding

8.7

Reviews

1 / 2

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

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 $79, while return flights cost around $250.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $784, however they can be found for as little as $157.

  • 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 (20 hours 39 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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