Flights from Sydney to Chicago

Compare Cheap Flights from Sydney to Chicago, United States

Looking for cheap flights to Chicago from Sydney? Use Webjet's deal finder to help you compare flights, carriers and seating classes all year round. You'll be sure to find the right flight to match your budget, plans and travel preferences.

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*Prices on this page are subject to change without notice, perform a search to view live pricing. Prices are inclusive of taxes and airline surcharges. Webjet fees per flight booking: Webjet Servicing Fee: Domestic $21.95, NZ/Pacific $24.95, International $32.95. Booking Price Guarantee: Domestic $12.95, NZ/Pacific $14.95, International $21.95. Varying payment fees are included in the price breakdown on Webjet’s checkout page, once your payment method has been selected.

^Flight prices are indicative, based on passenger numbers and may vary dependent on your individual flight dates. Prices were found by customers on the date in the right hand column labelled "Last Updated" and may vary. Complete a new search to view live pricing.

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What's on in Chicago?

Chicago Blues Festival

The Chicago Blues Festival is one of the best live events in the city. For three days, four stages play host to some of the top blues acts from across the country. For music lovers buying flights to Chicago, this is one event you don't want to miss!

Magnificent Mile Lights Festival

Kick the holiday season off in style with return flights to Chicago and the Magnificent Mile Lights Festival! It's a weekend-long event that has plenty of kid-friendly activities, such as ice carving contests and musical performances. The highlight of the festival for many people buying airfare to Chicago is the grand finale parade and the illumination of one million lights along Michigan Avenue.

St. Patrick's Day Parade

Need an excuse to buy those return flights to Chicago? Plan your trip around the city's St. Patrick's Day Parade. It’s a massive event that celebrates American Irish heritage. The event is more than four hours long, and you'll get to indulge in green beer, bagpipe tunes and all things Irish.

Taste of Chicago

Taste of Chicago is an event that will tantalise your tastebuds. Foodies travelling to the Windy City with flights to Chicago for the event can sample traditional deep-dish pizza, Chicago-style hot dogs and other specialities.

What is the best way to get around Chicago?

Chicago Transit Authority (CTA)

Chicago has an efficient public transportation system that zig-zags across the city. Hop on-board one of the eight L trains or use the 129 bus routes. When your flights to Chicago land at O'Hare International Airport (ORD), you can take the Blue Line train to downtown hotels. The buses make stops every few blocks around the city and several lines run a Night Owl service. The bus is an affordable and safe way to get back to your hotel if you're exploring the city’s nightlife offerings while holidaying on your airfare to Chicago.

Metra Rail

The Metra Rail is a great option for travellers buying tickets to Chicago and who have made hotel reservations in stays located in the city’s outlying suburbs. The service is a fast and easy way to get to the city centre with a one-way ticket costing on average $6.25 USD ($9.07 AUD).

Taxis and Ridesharing

One of the best parts about using Chicago's taxi service is that the cab drivers accept credit cards. You don't need to worry about having cash on you if you're in a rush to get somewhere. For a slightly cheaper option, you can use rideshare services to navigate the city once your flights to Chicago arrive at O'Hare International Airport (ORD). Keep in mind that you'll need to have a local sim card or data allowance when you’re unable to connect to WiFi.

Water taxis

Get off the streets and explore Chicago by boat. The Shoreline Water Taxi and the Chicago Water Taxi services are a fast, affordable and unique way for tourists to get around. The taxis have stops near some of Chicago's top attractions such as Chinatown, Michigan Avenue, Willis Tower and Museum Campus.

Biking

Did you know that Chicago is one of the friendliest cities in the world for cyclists? It boasts an impressive 320 kilometres of bike lanes, making it easy to take in the sights at your own pace. Keen cyclists buying flights to Chicago wanting to rent a bike can use Divvy. This is the city's bikeshare program, with more than 500 stations and 5,800 bikes available for rent 24 hours a day.

What are Chicago's most famous landmarks and monuments?

Art Institute of Chicago

The Art Institute of Chicago is world-famous for its thousands of artworks. But one of the main reasons art lovers buy flights to Chicago is to see the museum's Impressionist and post-Impressionist paintings.

Millennium Park

Millennium Park is located in downtown Chicago. In the centre is a 110-tonne sculpture called the Cloud Gate. It reflects its surroundings and is a wonderful spot for a photo op. Other attractions in the park include the Crown Fountain, the Lurie Garden and the Pritzker Pavilion. If you buy cheap flights to Chicago and you want to stay close to many of the top attractions, the area around Millennium Park is a great place to look for hotels.

Navy Pier

Once an amusement area and shipping facility, Navy Pier is now one of the best attractions in Chicago. Book your return flights to Chicago and spend a day exploring the 50 aces of gardens, shopping up a storm and dining out at the numerous restaurants. If you're buying cheap flights to Chicago for the whole family, don't miss out on the 45-metre Ferris wheel and the historic carousel! There's also a 3D Imax Theater, a Chicago Shakespeare Theatre and Crystal Gardens. The latter is a one-acre, six-storey indoor botanical garden!

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