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Cheap Flights to Chicago

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Home North America USA Illinois Cheap flights to Chicago, Illinois

Flights to Chicago in 2021

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, 22% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 4% potential price drop
Average price$1,384Average for round-trip flights in July 2021
Round-trip from$2,716From Sydney Kingsford Smith to Chicago
One-way from$14One-way flight from Sydney to Chicago

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
1 Dec - 15 Dec
$2,614pp
SYD
Sydney Kingsford Smith
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Fiji Airways
   
2 STOPS
SYD
Sydney Kingsford Smith
1 Dec - 15 Dec
$3,522pp
SYD
Sydney Kingsford Smith
Qatar Airways
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qatar Airways
 
1 STOP
SYD
Sydney Kingsford Smith
1 Dec - 15 Dec
$3,869pp
SYD
Sydney Kingsford Smith
Qatar Airways
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qatar Airways
 
1 STOP
SYD
Sydney Kingsford Smith

Cheapest prices for Chicago flights by month

The cheapest ticket to Chicago found for each month in 2021 based on historical flight searches by Cheapflights users.
January
$1,177
February
$1,217
March
$1,207
April
$1,268
May
$1,134
June
$1,287
July
$1,165
August
$1,186
September
$1,241
October
$1,219
November
$1,182
December
$1,415
At the present moment the cheapest month to fly to Chicago is currently May; with December being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

When is the best time to fly to Chicago?

Average Chicago flight ticket prices and weather conditions for 2021 and 2022 by month.
SYD - CHI
Price
$1,134 - $2,280
CHI
Temperature
1 - 29 °C
CHI
Precipitation
17 - 109 mm
Flying to Chicago in May is usually considered the best time to fly. However, you will find other deals are always available year round. July sees the temperatures in Chicago peak to their warmest. May tends, on average, to see the most amount of rainfall.

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 1 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 Tuesday. 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 in the afternoon 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.

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.

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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.

 

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Alternative, similarly priced destinations

See alternative destinations where airfare is generally forecast to be close to Chicago flight prices.

Find the best prices for you!

Cheap tickets to Chicago found by our users in Australia as recently as July 29, 2021.

Chicago, Illinois airports

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

Cheapest flights to USA

Not set on Chicago? See the cheapest flights to Australia. Airfare prices updated on July 29, 2021.
Home North America USA Illinois Cheap flights to Chicago, Illinois
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