Chicago flights and travel guide

The Windy City is calling your name, so take advantage of our cheap flights to Chicago and answer with a vacation to remember. You’ll have a great time in this city, located on the shore of Lake Michigan, with its combination of big city bustle and Midwestern charm. Cruise down the Chicago River, which is dyed green every St. Patrick’s Day, or take a walk along the lakefront to view that famous skyline. Chi-town’s known for its blustery politics, but it’s got a lot to offer a traveler looking for some good times and some good eats. Your stomach will surely thank you for the visit to this foodie hotspot. And don’t worry about that food budget. With the money you save on cheap airfare, you’ll be able to snack on everything from escargot to Chicago hot dogs. So make room in your stomach, because your wallet will be stuffed.

Chicago flights to O’Hare International Airport (ORD) or Midway International Airport (MDW) take you straight to the Windy City. In no time at all, you can hop on an elevated train and cruise downtown to the Loop for an architectural walking tour. Look up at some of the first skyscrapers in the world or climb to the top of some of the tallest. The SkyDeck in Willis Tower, formerly known as the Sears Tower, has spectacular views of both the city and lake. A flight to Chicago also lets you participate in America’s national pastime. Catch a fly ball while the Chicago Cubs play baseball at legendary Wrigley Field. After your cheap flight to Chicago, continue saving money and take advantage of Chicago’s free outdoor activities. Walk among the sculptures in Millennium Park. You may want to book a one-way flight to Chicago, because you’ll have such a good time.

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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, and are prone to thunderstorms. August is usually the wettest month of the year. 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.

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Best Time to Fly to Chicago

Chicago’s seasons are intense – it’s hot in the summer and cold in the winter – but savvy travelers can always find cheap airline tickets 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 neighborhoods 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 cheap hotels and 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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