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Find cheap flights to Chicago, United States of America

The city of Chicago in the United States is served by two major airports - the Chicago O'Hare International Airport and the Chicago Midway International Airport. Major airlines that arrive into Chicago include Cathay Pacific, United Airlines, American Airlines, Etihad Airways and Air Canada.

Chicago O'Hare International Airport

  • Estimated distance from city: 29km
  • Estimated cost of taxi from airport to city: SGD 58
  • Estimated duration from airport to city: 20 minutes

Chicago Midway International Airport

  • Estimated distance from city: 16km
  • Estimated cost of taxi from airport to city: SGD 43
  • Estimated duration from airport to city: 20 minutes

Cheap Chicago Flights

Travel smarter and save more when you search for the best flight available on Skyscanner. Want to know which month to travel to get more bang for your buck? All you have to do is to enter where you want to go to (in this case, Chicago) and then select “whole month” on the depart and return fields before clicking on the “cheapest month”. You are also able to specify whether you want a direct flight or not based on your port of disembarkation and embarkation.

Best Time to Visit Chicago

Chicago enjoys a humid continental climate with four distinct seasons. Spring (March to May) is always a great time to visit this beautiful city and temperatures are generally stable between 10 and 20 degree Celsius. With that being said, if you are interested in the festivals that take place in Chicago, the best time to visit is during Autumn (September to November). It is also worth noting that accommodation prices in the city generally soar in the Summer (June to August) where people are drawn to Lake Michigan and various baseball games. Winter (December to February) is generally avoided by travellers as it is not uncommon to see temperatures dipping to -7 degree Celsius in the early mornings.

Things to do in Chicago

Chicago is a huge city and one of the best ways to take in the sights of this city is to hop on Chicago’s First Lady Cruise. If you prefer to break out a sweat while seeing this city, check out Bobby’s Bike Hike Chicago which is arguably the second best way to see what this city has to offer. No matter which season you visit, there is always something going on in the city - be it a baseball match, a play, a musical or simply street festivals. Make sure you take a walk around the Millennium Park to check out the interesting sculptures and enjoy a slice of nature. Finally, no visit to Chicago is complete without a drive to the world-famous Lake Michigan (especially in the Summer!).

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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.