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Sydney to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Sydney to Chicago

Departure Arrival Travel dates Round-trip
SYD CHI Sat, Nov 15 - Sat, Dec 6 $1,494
SYD CHI Thu, Oct 9 - Mon, Oct 13 $1,521
SYD CHI Sun, Nov 16 - Fri, Nov 21 $1,598
SYD CHI Sun, Nov 16 - Fri, Nov 21 $1,720
SYD CHI Sun, Nov 16 - Fri, Nov 21 $1,782
SYD CHI Sun, Nov 16 - Fri, Nov 21 $1,793
SYD CHI Sun, Nov 16 - Fri, Nov 21 $1,920
SYD CHI Tue, Sep 2 - Sun, Sep 7 $2,071
SYD CHI Sun, Aug 10 - Thu, Aug 28 $2,082
SYD CHI Wed, Oct 1 - Tue, Oct 14 $2,148
SYD CHI Thu, Oct 9 - Mon, Oct 13 $2,229
SYD CHI Thu, Oct 9 - Mon, Oct 13 $2,305
SYD CHI Sat, Nov 15 - Sat, Dec 6 $4,979
SYD CHI Wed, Oct 1 - Tue, Oct 14 $8,693

Sydney and Chicago airports and terminals

Airports in Sydney NS, AU
map of airports in Sydney
  • 1

    Sydney Airport (SYD)

    Distance from City Center: 5.7 miles

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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

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Cheap flights from Sydney to Chicago

Sun Mon Tue Wed Thu Fri Sat
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10 11
$2,027
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31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 165 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 68 reviews

6500 SOUTH CICERO AVE Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 22 reviews

6530 S. Cicero Avenue Map

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 30 reviews

6540 S. Cicero Ave. Map

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.6 / 5 11 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $99

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 147 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

August

Lowest roundtrip airfare in August from Sydney to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Aug 11 Sydney (SYD) Chicago (ORD) United Airlines $2,027
Earn $20.27
Return Mon, Sep 8 Chicago (ORD) Sydney (SYD) United Airlines
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September

Lowest roundtrip airfare in September from Sydney to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 6 Sydney (SYD) Chicago (ORD) Korean Air $1,904
Earn $19.04
Return Sun, Oct 26 Chicago (ORD) Sydney (SYD) Korean Air
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October

Cheapest weekend flights in October from Sydney to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 9 Sydney (SYD) Chicago (ORD) Qantas $1,521
Earn $15.21
Return Mon, Oct 13 Chicago (ORD) Sydney (SYD) Qantas

Lowest roundtrip airfare in October from Sydney to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 9 Sydney (SYD) Chicago (ORD) Qantas $1,521
Earn $15.21
Return Mon, Oct 13 Chicago (ORD) Sydney (SYD) Qantas
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Find Cheap Flights from Sydney to Chicago

JA Douglas McCurdy Airport

Booking cheap flights from Sydney, Nova Scotia, is easy with Orbitz.com. JA Douglas McCurdy Airport is located almost six miles northeast of Sydney and is the main airport that serves those flying out of the area. Air Canada Express, Air Saint-Pierre, Westjet and Canadian North are major airlines that have planes flying in and out of this airport. Book your flights on Orbitz.com, and you'll find the best deals on flights leaving from JA Douglas McCurdy Airport.

Parking and Transportation

Busses, trains and taxis are available throughout the city of Sydney. As of 2012, the city of Sydney has over 300 bus routes and 302 train stations. Both busses and trains provide direct transportation to JA Douglas McCurdy Airport. City Wide Taxi is a large taxi company that provides flat rates to those traveling to the airport. Your rate will depend on where in the city you are located. JA Douglas McCurdy Airport also has a large parking lot, and there are daily, weekly, monthly and yearly rates available to those who choose to drive. Parking costs $6.50 per day, $39 per week and $156 per month. Yearly parking costs $475.

Airport Dining

JA Douglas McCurdy Airport has a reception area where you can grab a cup of coffee or a bite to eat while waiting on your flight. You can also bring your own food to the reception area if you have time to spare before leaving Sydney. Book your flights from Sydney to anywhere in the world on Orbitz.com to find the best travel deals online.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.