Fly from
Budget
$1,364 - $2,666
Route
Depart
Return
Price
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 4/9
2 stops35h 08m
Chicago O'Hare Intl
Sun 15/9
1 stop27h 15m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 14/8
2 stops23h 09m
Chicago O'Hare Intl
Wed 4/9
1 stop20h 50m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 31/10
1 stop35h 55m
Chicago O'Hare Intl
Sun 3/11
2 stops44h 05m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 13/6
1 stop37h 20m
Chicago O'Hare Intl
Mon 15/7
1 stop22h 44m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 31/10
1 stop40h 30m
Chicago O'Hare Intl
Sun 3/11
1 stop26h 30m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 19/6
1 stop45h 50m
Chicago O'Hare Intl
Mon 22/7
2 stops32h 48m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 18/6
2 stops31h 01m
Chicago O'Hare Intl
Tue 25/6
2 stops54h 54m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 19/6
1 stop45h 50m
Chicago O'Hare Intl
Sat 20/7
1 stop37h 05m
Sydney Kingsford SmithChicago Midway
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Wed 4/9
2 stops22h 49m
Chicago Midway
Sun 15/9
2 stops26h 25m
Currently, February is the cheapest month in which you can book a flight to Chicago (average of $928). Flying to Chicago in December will prove the most costly (average of $1,591). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
January
$1,628
February
$1,386
March
$1,574
April
$1,852
May
$1,742
June
$1,773
July
$1,906
August
$1,891
September
$1,722
October
$1,667
November
$1,916
December
$2,377
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.
CHI Temperature | -5 - 23 °C |
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If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
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.