We work with more than 300 partners to bring you better travel deals
Cheap Flights to Chicago
|Popular in||December||High demand for flights, 23% potential price rise|
|Cheapest in||May||Best time to find cheap flights, 4% potential price drop|
|Average price||$1,226||Average for round-trip flights in August 2020|
|Round-trip from||$1.684||From Melbourne to Chicago|
|One-way from||$548||One-way flight from Melbourne to Chicago|
Cheapest prices for Chicago flights by month
When is the best time to fly to Chicago?
Choose a month below to see average flight price and weather conditions.
MEL - CHI
$1,160 - $2,332
1 - 29 °C
17 - 109 mm
When is the best time to book a flight to Chicago?
The price you pay for your flight to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Which day is cheapest to fly to Chicago?
The cheapest flights to Chicago are usually found when departing on a Wednesday. The departure day with the highest cost at present is Saturday.
What time of day is cheapest to fly to Chicago?
At the moment, flights in the morning are likely to offer the best value for money for your Chicago trip. A flight at midday will more often than not be of higher cost.
When to fly
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.
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.
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.