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Home North America USA Illinois Cheap flights to Chicago, Illinois

Cheap Flights to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.

Cheapest Prices for Chicago flights by month

January
₱45,052
February
₱43,120
March
₱36,548
April
₱40,079
May
₱44,382
June
₱40,524
July
₱44,634
August
₱42,993
September
₱33,615
October
₱35,933
November
₱33,303
December
₱38,867
Currently, November is the cheapest month in which you can book a flight to Chicago. Flying to Chicago in January will prove the most costly. There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the best time to fly to Chicago?

Choose a month below to see average flight price and weather conditions.
ZAM - CHI
Price
₱33,303 - ₱80,303
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm
October is typically the best time to fly to Chicago, but there are other times where great deals are available. July sees the temperatures in Chicago peak to their warmest. May tends, on average, to see the most amount of rainfall.

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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