Cheap flights to Chicago

ICT — CHI
21 May — 28 May1
Return
1 adult
Economy
From?
To?
Sat 21/5
Sat 28/5

Flights to Chicago in 2022

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
Popular inJanuaryHigh demand for flights, 18% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 4% potential price drop
Average price$1,252Average for return flights in May 2022
Return from$1,379From Sydney Kingsford Smith to Chicago
One-way from$1,036One-way flight from Sydney Kingsford Smith (SYD) to Chicago

Cheap flights to Chicago in May, June 2022

The best prices found for CHI flights for May, June
11 Jun. - 19 Jun.
SYD

Sydney Kingsford Smith

ORD

Chicago O'Hare Intl

2 stops

37h 39m
ORD

Chicago O'Hare Intl

SYD

Sydney Kingsford Smith

1 stop

22h 40m
$1,800

Air Canada

View Deal

Deal found 15/5/22

6 Jun. - 27 Jun.
SYD

Sydney Kingsford Smith

ORD

Chicago O'Hare Intl

1 stop

25h 45m
ORD

Chicago O'Hare Intl

SYD

Sydney Kingsford Smith

2 stops

43h 25m
$1,804

Air Canada

View Deal

Deal found 14/5/22

6 Jun. - 27 Jun.
SYD

Sydney Kingsford Smith

ORD

Chicago O'Hare Intl

2 stops

38h 15m
ORD

Chicago O'Hare Intl

SYD

Sydney Kingsford Smith

2 stops

43h 25m
$1,811

Air Canada

View Deal

Deal found 14/5/22

Chicago 2022 flight deals

Cheap flights to Chicago found for this year
12 Oct. - 22 Nov.
SYD

Sydney Kingsford Smith

ORD

Chicago O'Hare Intl

1 stop

20h 26m
ORD

Chicago O'Hare Intl

SYD

Sydney Kingsford Smith

2 stops

31h 20m
$1,379

Air Canada

View Deal

Deal found 16/5/22

12 Oct. - 22 Nov.
SYD

Sydney Kingsford Smith

ORD

Chicago O'Hare Intl

1 stop

20h 26m
ORD

Chicago O'Hare Intl

SYD

Sydney Kingsford Smith

1 stop

25h 20m
$1,386

Air Canada

View Deal

Deal found 16/5/22

12 Oct. - 22 Nov.
SYD

Sydney Kingsford Smith

ORD

Chicago O'Hare Intl

2 stops

22h 26m
ORD

Chicago O'Hare Intl

SYD

Sydney Kingsford Smith

2 stops

31h 20m
$1,421

Air Canada

View Deal

Deal found 16/5/22

When is the best time to fly to Chicago?

Average Chicago flight ticket prices and weather conditions for 2022 and 2023 by month

SYD - CHI

Price

$1,904 - $3,078

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

Which day is cheapest to fly to Chicago?

At the moment, Tuesday is the most economical day to take a flight to Chicago. Sunday is likely to be the most costly.

What time of day is cheapest to fly to Chicago?

Chicago flights can be made cheaper if you choose a flight in the morning. Booking a flight at midday will likely mean higher prices.

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.

Peak Season

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.

Off-Peak Season

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.

Why 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.

Getting around Chicago

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.

Travel Tips

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.

Other local departures to Chicago from Australia

Chicago, Illinois airports

See all airports in Chicago, select one to find and compare flight prices.