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$651+ 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 30/1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
29 Dec — 5 Jan1
1 adult

Flights to Chicago in 2024

Find the latest flights to Chicago in 2024, 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 December 2024.

Return from

$1,493

One-way from

$651

Popular in

December

Cheapest in

March

Average price

$2,516
23/1-5/2
  • 23/1-5/2
  • 4 total stops
  • 66h 16m total
  • Sydney to Chicago
30/1
  • 30/1
  • 2 total stops
  • 38h 15m total
  • Sydney to Chicago
High demand for flights, 6% potential price rise
Best time to find cheap flights, 2% potential price drop
Average for return flights in December 2024

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 December 2024.

Tue 24/1211:20SYD - ORD
3 stops40h 34mAir Canada
Wed 8/115:40ORD - SYD
2 stops48h 05mAir Canada
Deal found 22/12$2,375
Wed 25/1211:20SYD - ORD
1 stop20h 18mUnited Airlines
Sat 4/122:00ORD - SYD
1 stop39h 20mUnited Airlines
Deal found 21/12$2,501
Tue 31/1207:05SYD - ORD
3 stops33h 05mAir Tahiti Nui
Tue 14/117:40ORD - SYD
3 stops31h 00mAir Tahiti Nui
Deal found 23/12$2,650
Tue 31/1211:20SYD - ORD
1 stop24h 35mVirgin Australia
Wed 15/114:35ORD - SYD
1 stop25h 40mVirgin Australia
Deal found 23/12$2,969
Tue 24/1208:00SYD - ORD
3 stops29h 59mMultiple Airlines
Sat 4/113:35ORD - SYD
2 stops24h 50mMultiple Airlines
Deal found 22/12$3,714
Tue 31/1214:15SYD - MDW
2 stops24h 51mDelta
Tue 14/114:08MDW - SYD
2 stops25h 27mDelta
Deal found 23/12$4,530

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 December 2024.

Fly from

Any airport

Route

Depart

Return

Price

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 23/1

06:15-23:13

2 stops33h 58m

Chicago O'Hare Intl

Wed 5/2

11:12-12:30

2 stops32h 18m

$1,493

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 10/2

11:20-19:55

2 stops25h 35m

Chicago O'Hare Intl

Thu 20/2

07:20-09:35

2 stops33h 15m

$1,587

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 16/5

20:55-08:40

1 stop26h 45m

Chicago O'Hare Intl

Fri 23/5

07:15-09:25

2 stops59h 10m

$1,970

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 23/1

11:15-17:45

1 stop23h 30m

Chicago O'Hare Intl

Fri 31/1

17:40-09:00

1 stop22h 20m

$1,989

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 13/2

14:15-22:20

2 stops25h 05m

Chicago Midway

Sun 23/2

14:08-08:35

2 stops25h 27m

$2,068

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 23/1

11:15-05:05

1 stop34h 50m

Chicago O'Hare Intl

Wed 5/2

13:13-06:35

1 stop24h 22m

$2,068

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Fri 16/5

09:30-21:19

2 stops26h 49m

Chicago O'Hare Intl

Fri 23/5

12:45-07:00

2 stops27h 15m

$2,205

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 23/1

11:05-13:00

1 stop42h 55m

Chicago O'Hare Intl

Wed 5/2

14:40-17:55

2 stops34h 15m

$2,472

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 23/1

08:55-19:31

3 stops27h 36m

Chicago O'Hare Intl

Fri 31/1

17:40-17:40

3 stops31h 00m

$2,663

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 12/4

21:45-06:17

3 stops47h 32m

Chicago O'Hare Intl

Thu 24/4

12:05-08:25

3 stops53h 20m

$3,569

Flights are sorted by cheapest return flights first.

Deals found on 23/12

Showing 1-10 of 31 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 20 December 2024.

Booking 24 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 11 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 Air New Zealand, 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 24 December 2024.
Read through reviews of airlines servicing Chicago, such as United Airlines, Air Canada and Air Tahiti Nui. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.7
Very Good
63 reviews

Overall

8.7

Comfort

8.0

Crew

9.0

Boarding

8.6

Food

7.7

Entertainment

7.2

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.

8.7
Very Good
63 reviews
8.7
Very Good
63 reviews

Overall

8.7

Comfort

8.0

Crew

9.0

Boarding

8.6

Food

7.7

Entertainment

7.2

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.

8.4
Very Good
841 reviews
8.7
Very Good
63 reviews

Overall

8.7

Comfort

8.0

Crew

9.0

Boarding

8.6

Food

7.7

Entertainment

7.2

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
1,439 reviews
8.7
Very Good
63 reviews

Overall

8.7

Comfort

8.0

Crew

9.0

Boarding

8.6

Food

7.7

Entertainment

7.2

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
1,330 reviews
8.7
Very Good
63 reviews

Overall

8.7

Comfort

8.0

Crew

9.0

Boarding

8.6

Food

7.7

Entertainment

7.2

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
8,588 reviews
8.7
Very Good
63 reviews

Overall

8.7

Comfort

8.0

Crew

9.0

Boarding

8.6

Food

7.7

Entertainment

7.2

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, 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 Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost $218, while return flights cost around $459.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around $287, however they can be found for as little as $287.

  • 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 44 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).

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Airports serving Chicago

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