Cheap flights to Chicago

ORL — CHI
4 Oct — 11 Oct1
Return
1 adult
Economy
From?
To?
Tue 4-10
Tue 11-10

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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 inAugustHigh demand for flights, 21% potential price rise
Cheapest inDecemberBest time to find cheap flights, 4% potential price drop
Average priceS$ 1,773Average for return flights in September 2022
Return fromS$ 948From Singapore Changi to Chicago
One-way fromS$ 634One-way flight from Singapore Changi (SIN) to Chicago

Cheap flights to Chicago in September, October 2022

The best prices found for CHI flights for September, October
9 Oct - 12 Oct
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

38h 30m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

22h 55m
S$ 1,394

Japan Airlines

Pick Dates

Deal found 27-9-22

2 Oct - 27 Nov
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

2 stops

46h 11m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

28h 10m
S$ 1,395

United Airlines

Pick Dates

Deal found 28-9-22

30 Oct - 4 Nov
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

2 stops

60h 01m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

2 stops

29h 10m
S$ 1,397

Japan Airlines

Pick Dates

Deal found 27-9-22

Chicago 2022 flight deals

Cheap flights to Chicago found for this year
1 Nov - 7 Nov
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

42h 00m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

24h 40m
S$ 951

Multiple Airlines

Pick Dates

Deal found 27-9-22

5 Dec - 26 Jan
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

29h 15m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

24h 40m
S$ 1,255

Multiple Airlines

Pick Dates

Deal found 28-9-22

6 Nov - 10 Nov
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

42h 00m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

24h 40m
S$ 1,309

Multiple Airlines

Pick Dates

Deal found 27-9-22

Last minute flights to Chicago

Late deals on return flights to Chicago, departing today and this week
9 Oct - 12 Oct
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

38h 30m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

22h 55m
S$ 1,394

Japan Airlines

Pick Dates

Deal found 27-9-22

9 Oct - 12 Oct
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

2 stops

40h 25m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

1 stop

22h 55m
S$ 1,407

Japan Airlines

Pick Dates

Deal found 27-9-22

9 Oct - 12 Oct
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

2 stops

40h 25m
ORD

Chicago O'Hare Intl

SIN

Singapore Changi

2 stops

46h 00m
S$ 1,423

Japan Airlines

Pick Dates

Deal found 27-9-22

One-way flights to Chicago

The cheapest one-way flights to Chicago
20 Feb
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

26h 55m
S$ 634

Multiple Airlines

Pick Dates

Deal found 28-9-22

10 Feb
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

1 stop

32h 30m
S$ 679

Multiple Airlines

Pick Dates

Deal found 28-9-22

21 Feb
SIN

Singapore Changi

ORD

Chicago O'Hare Intl

2 stops

31h 35m
S$ 719

Multiple Airlines

Pick Dates

Deal found 28-9-22

When is the best time to fly to Chicago?

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

SIN - CHI

Price

S$ 1,233 - S$ 3,263

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

When is the best time to book a flight to Chicago?

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Which day is cheapest to fly to Chicago?

Tuesday is currently, on average, the cheapest day to fly to Chicago. Flying on Friday will result in higher flight prices.

What time of day is cheapest to fly to Chicago?

Flights at midday are typically the cheapest time of the day to fly to Chicago. Flights in the afternoon are usually the most expensive.

As Frank Sinatra crooned, “Chicago is my kind of town.” And many visitors agree. A trip to Chicago is best spent shopping on the Miracle Mile, stepping back in time at the National History Museum, touring the artist’s lofts in the heart of the city, and enjoying some cool jazz at one of Chicago’s many jazz clubs.

Chicago, with its varied and eclectic sampling of modern architecture, rests on the shores of Lake Michigan in the heart of the American Midwest. Flights to Chicago land travellers at either Midway Airport or O’Hare International Airport, both about 30 minutes from downtown Chicago, but a car isn’t needed to get around. Take a taxi or hop the commuter rail from your Chicago flight to downtown and then tour the city by foot. Stop by the Sears Tower, the tallest building in the United States, and take an elevator ride to the Sears Tower Skydeck for unprecedented views of the city.

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Chicago climate

Chicago has an extreme climate with very hot summers and bitterly cold winters, its lakeside setting only slightly moderating the temperatures and adding some humidity to the atmosphere. Chicago has distinct seasons, with a short spring, when temperatures are moderate and nights frosty. Summers are hot, sunny and humid, from June to the end of September, with cool evenings when breezes blow in from Lake Michigan. Autumn is a lovely time of year when the air is crisp and cool, with blue skies and sunshine. Winters in Chicago are icy and prone to cold, harsh winds. Snow is common, and it is also very rainy during the winter months.

When is the best time to fly to Chicago?

Peak season:

Summer 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.  September can be the most enjoyable and mild month of the year but there’s less going on during this period.

Off season:

January to March is when Chicago is least busy and deals on hotels and cheap flights to Chicago are usually 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.

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Getting around Chicago

No need to worry about getting around Chicago. There are plenty of ways to get around. Hop on the El, short for elevated train, the city’s subway system, or one of the buses that runs all over the city. For information about fares and routes, check out the website for the Chicago Transit Authority. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Biking is becoming increasingly popular around the city, thanks to the city’s former mayor encouraging residents to ride their bikes as a mode of transportation. With all of Chicago’s lakefront property, biking can be a great way to enjoy the city. 

What is good to know if travelling to Chicago?

  • Any shopping in Chicago has to begin on State Street, in the centre of the Loop. The Marshall Field’s flagship department store opened in 1852 there. Check out the famed “Magnificent Mile” along Michigan Avenue from the Chicago River to Oak Street for specialty shops and boutiques with designers from Paris, Milan and Manhattan blending with Chicago’s Gold Coast style.
  • The Chicago Cultural Centre houses one of the city’s official Visitor Information Centres and offers more than 600 free art programmes annually.
  • Along the shores of Lake Michigan, you’ll find Chicago’s cultural delights including the Art Institute of Chicago, the Goodman Theatre, the Lyric Opera at the Civic Opera House building, and the Chicago Symphony Orchestra.
  • Chicago’s lakefront is almost exclusively recreational park area from north to south, and features Grant Park, the home of Buckingham Fountain, the Petrillo Bandshell, the Grant Park Symphony (where free concerts are presented throughout the summer), and Chicago’s annual two-week food orgy, the Taste of Chicago, where more than three million people “chow down”.
  • The beauty of Chicago springs from the tragedy of the Great Chicago Fire in 1871 that claimed 300 lives, left 90,000 Chicagoans homeless and destroyed $200 million worth of property. From this disaster came the opportunity to plan and rebuild the entire city.
  • Chicago is also home to the nine time world-championship football team, the Chicago Bears and Wrigley Field, the second-oldest ballpark in the Major League baseball, built in 1914, just behind Boston’s Fenway Park, built in 1912.

Chicago, Illinois airports

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

Search flights to Chicago by cabin class

Business Classfrom S$ 5,710/person
Economyfrom S$ 1,000/person