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, 5% potential price rise
Cheapest inSeptemberBest time to find cheap flights, 1% potential price drop
Average priceS$ 1,460Average for round-trip flights in May 2021
Round-trip fromS$ 1,284From Singapore to Chicago
One-way fromS$ 13One-way flight from Singapore to 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
S$ 1,088
February
S$ 1,175
March
S$ 1,048
April
S$ 1,311
May
S$ 1,186
June
S$ 1,275
July
S$ 1,214
August
S$ 1,562
September
S$ 1,215
October
S$ 1,365
November
S$ 1,290
December
S$ 1,451
At the present moment the cheapest month to fly to Chicago is currently March; with August 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.
SIN - CHI
Price
S$ 1,048 - S$ 1,881
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm
Whilst there are several times of the year to choose from, February is seen as the time to fly to Chicago, however, it is possible to get good deals throughout the year. If weather is an important factor for you when considering when to fly to Chicago, the warmest period tends to be July, with the wettest being May.

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 61 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 day to fly to Chicago is usually Friday. At the moment, Saturday is the most expensive.

What time of day is cheapest to fly to Chicago?

To get the best value, try booking a flight in the afternoon when visiting Chicago. Generally the prices will increase for flights at midday as these tend to have higher demand.

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.

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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. 

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Cheap flights to Chicago in May, June 2021

The best prices found for ORD flights for May, June
6 May - 10 May
S$ 1,262pp
SIN
Singapore Changi
Etihad Airways
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Etihad Airways
 
1 STOP
SIN
Singapore Changi
6 May - 9 May
S$ 1,296pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi
6 May - 9 May
S$ 1,302pp
SIN
Singapore Changi
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
SIN
Singapore Changi

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
6 May - 10 May
S$ 1,262pp
SIN
Singapore Changi
Etihad Airways
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Etihad Airways
 
1 STOP
SIN
Singapore Changi
6 May - 9 May
S$ 1,296pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi
25 Oct - 29 Oct
S$ 1,297pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi

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 Singapore as recently as May 06, 2021.

Chicago, Illinois airports

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