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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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Know Before You Go
- Head to the nearest cocktail bar and try Chicago's unique liqueur called Malört. The bitter wormwood drink is rarely found outside of the city, and despite its less than pleasant taste, mixologists are intent on making the liqueur more palatable.
- If you are a foodie, make room in your budget to visit some of Chicago's top restaurants in The West Loop. Or if money's no object you can even dine at one of the best restaurants in the world, Alinea.
- Chicago is famous around the world for its architecture. If you want to learn more about the city's unique buildings, go on a tour. There are over 85 to choose from that will take you past Chicago's iconic skyscrapers, hotels and the houses of Frank Lloyd Wright.
- Pack your swimming costume and head to the city's 27 beaches. Despite not being near an ocean, Lake Michigan is the perfect stand-in for a day of sun worship and relaxation.
Getting Around Chicago
The most affordable way to get around the city is using your feet. However, the Windy City is far too big to rely solely on walking. It's easier to use public transport to get to a certain neighbourhood and then go on foot from there.
- The L train is the city's subway system. It has stops at 145 stations around town with certain lines running 24 hours a day. Fares start at USD 2.25 one-way, or you can buy an unlimited three or seven day pass for under USD 30.
- Chicago also has an extensive bus system with 130 routes going to almost every attraction. Several bus routes operate 24 hours a day, with others stopping around 11 pm or 2 am. A single one-way fare will cost you USD 2.25 and day passes range between USD 10 and USD 30 depending on the number of days covered.
- If you need to get into Chicago's suburbs, use the Metra Rail. It's the most reliable form of transportation and serves 11 lines from 4 am to 2 am every day. A one-way ride will cost you anywhere from USD 3.50 to USD 10.50, depending on the distance travelled.
- Taxis are the more expensive way to get around the city, but they are convenient. You can hail a cab from the street or call ahead for a planned pickup. Meters start at USD 4 and each mile costs USD 3.60. If you are on a budget, ridesharing apps like Uber and Lyft are also available throughout the city.
- If you want more freedom in getting around, you can hire a car. Chicago is an easy city to navigate with its grid layout, but you should set aside budget for its expensive parking. It's also not advised to hire a car during the winter months if you don't have experience driving in snow.
When is The Best Time to Visit Chicago?
The best times to visit Chicago are from April to May and September to October. These shoulder seasons are still warm with thinner crowds and a variety of festivals to keep you busy. You'll also be able to find better deals on flights and accommodation during these months.
If you do go during spring or autumn, expect some occasional rain and double check the opening hours for outdoor attractions. Navy Pier and Lincoln Park Zoo switch to reduced hours before the winter season.
June to August are Chicago's summer months and high season. Hotel rates are at their highest and rooms are hard to find without booking in advance. While the weather is warm during this time, temperatures can fluctuate, so pack a variety of clothes in case a cold front hits the city.
Chicago's winter months (November to March) see the city virtually empty of tourists. If you don't mind the freezing temperatures, you'll have the city to yourself and plenty of airfare and hotel deals to choose from.
Airports in Chicago
Chicago O'Hare International Airport
Chicago O'Hare is located 27 km from the city centre and is the primary airport for the Chicago metropolitan area. It's the third busiest airport in the United States and has direct flights to over 200 destinations around the world. The airport serves as a hub for United Airlines and American Airlines and is a focus city for low-cost carriers Frontier and Spirit Airlines.
Chicago Midway International Airport
Chicago Midway is 16 km from the city and serves Chicago as a secondary airport. It's mainly used for domestic flights and is a focus city for low-cost carrier Southwest Airlines. Currently, the airline controls 34 of the airport's 43 gates and operates 236 daily flights to 69 destinations.
Getting From Chicago Airports To Downtown Chicago
The cheapest way to get from either of Chicago's airports to the city centre is with the 24-hour train system. The Blue Line from O'Hare will take 45 minutes and cost about USD 5 one-way. The Orange Line from Midway takes 25 minutes to reach the city and fares are USD 2.25 for a single journey.
If you don't want to take public transport to get into the city, taxis are outside the Arrivals terminal at both airports. From O'Hare, the trip should cost about USD 40 with tip and the drive takes about 35 minutes. A taxi from Midway will be slightly cheaper, costing you USD 30 one-way.
Other options to get into downtown Chicago include shared shuttle services. While it's a more affordable option than taking a taxi, your travel time will be longer. Prices depend on the service provider you choose but can be anything from USD 14 to USD 56 one way.
