|Popular in||January||High demand for flights, 22% potential price rise|
|Cheapest in||February||Best time to find cheap flights, 4% potential price drop|
|Average price||$1,272||Average for round-trip flights in October 2021|
|Round-trip from||$1,313||From Sydney Kingsford Smith to Chicago|
|One-way from||$14||One-way flight from Sydney Kingsford Smith (SYD) to Chicago|
Information is based on travel restrictions for travel to Chicago within the United States
Most visitors from USA need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.
COVID-19 testing requirements
Visitors from USA must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.
Visitors from USA are not required to quarantine after entering Chicago.
Returning to USA from Chicago
COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to USA.
Visitors from Chicago are not required to quarantine after entering USA.
SYD - CHI
$1,133 - $2,279
1 - 29 °C
17 - 109 mm
Chicago’s seasons are intense – it’s hot in the summer and cold in the winter – but savvy travellers can always find cheap flights to Chicago.
Summer is between June and August and it is the peak of the festival season in the Chicago area with major events taking place in the parks and neighbourhoods every weekend, in spite of the heat and humidity from the Lake. Taste of Chicago, taking place mid-July at the lakefront is an outdoor food festival which showcases the variety of cuisines and local flavours accompanied by live music. Cheap flights to Chicago are more difficult to find during this popular festival. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.
September can be the most enjoyable and mild month of the year but there’s less going on during this period.
January to March is least busy making cheap flights to Chicago and hotel deals attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.
Chicago is a skyscraper metropolis and a feat of modern architecture as well as home to what was once the world’s tallest building, Sears Tower. Chicago may not be a traditional tourist destination but you will find that the Second City is well worth a visit. As the hub of the Midwest, Chicago is not to be overlooked. Its picturesque skyline is reflected in the waters of Lake Michigan. World-class museums of art and science, fine public art, huge parks and sandy beaches and a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups) make it an unbeatable destination for a holiday. First stop should be the lakefront, from Lakeview to Oak Street Beach, the entire area is bustling for things for you to do and to see. Take a cheap flight to Chicago and the city will match your passion.
Chicago has long been thought of as the nation’s second city – indeed, Chicagoans only grudgingly admit that New York occupies first place. The city’s central area, including the Loop and the Magnificent Mile, is famous for its combination of modern and historic architecture. Chicago is also home to many of the country’s best museums and art galleries, including the Field Museum of Science and Industry and, reflecting the city’s industrial heritage, the Museum of Science and Industry.
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.
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.
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.