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$1,272Average for round-trip flights in October 2021
Round-trip from$1,313From Sydney Kingsford Smith to Chicago
One-way from$14One-way flight from Sydney Kingsford Smith (SYD) to Chicago

Cheap flights to Chicago in October, November 2021

The best prices found for ORD flights for October, November
18 Nov - 16 Apr
$1,745pp
SYD
Sydney Kingsford Smith
ANA
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
ANA
 
1 STOP
SYD
Sydney Kingsford Smith
18 Nov - 16 Apr
$1,915pp
SYD
Sydney Kingsford Smith
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SYD
Sydney Kingsford Smith
18 Nov - 16 Apr
$1,956pp
SYD
Sydney Kingsford Smith
Multiple airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SYD
Sydney Kingsford Smith

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
16 Dec - 4 Jan
$1,576pp
SYD
Sydney Kingsford Smith
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SYD
Sydney Kingsford Smith
20 Dec - 8 Jan
$1,674pp
SYD
Sydney Kingsford Smith
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SYD
Sydney Kingsford Smith
18 Nov - 16 Apr
$1,745pp
SYD
Sydney Kingsford Smith
ANA
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
ANA
 
1 STOP
SYD
Sydney Kingsford Smith

Last minute flights to Chicago

Late deals on return flights to Chicago, departing today and this week
20 Oct - 28 Oct
$18,132pp
SYD
Sydney Kingsford Smith
Multiple airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
SYD
Sydney Kingsford Smith
20 Oct - 28 Oct
$18,263pp
SYD
Sydney Kingsford Smith
Multiple airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
SYD
Sydney Kingsford Smith

COVID Restrictions

View COVID Travel Restrictions for Chicago

Can I fly to Chicago from USA right now?

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.

Quarantine requirements
Visitors from USA are not required to quarantine after entering Chicago.

Can I fly back to USA from 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.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering USA.

Hide COVID Travel Restrictions for Chicago

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
$1,234
February
$1,219
March
$1,209
April
$1,412
May
$1,243
June
$1,277
July
$1,245
August
$1,196
September
$1,235
October
$1,201
November
$1,117
December
$1,549
Currently, the cheapest month for flights to Chicago is November. The most expensive month for flights is December. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

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
$1,133 - $2,279
CHI
Temperature
1 - 29 °C
CHI
Precipitation
17 - 109 mm
The best time to fly to Chicago is during July, but great deals can be found at other times. 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?

Booking 1 days in advance of your planned departure date is, on average, the best time to get cheap flights to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Which day is cheapest to fly to Chicago?

At the moment, Tuesday is the most economical day to take a flight to Chicago. Saturday 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 in the afternoon 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.

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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 October 14, 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 October 14, 2021.
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