Ah, Chicago. One of the United States’ most popular destinations… and for good reason. There are so many great things to do here, that making a list of activities would really never do it justice. From its rich technological history to the delicious food to its stunning skyline to its die-hard Cubs fans who recently celebrated their first World Series win in over 100 years, Chicago is truly a one-of-a-kind city. With so many great things to do in one city, we’ve narrowed it down to one activity per season that we think you really cannot miss out on.

Drink at a Rooftop Bar During the Summer

Enjoy one of the world’s most recognizable skylines from one of Chicago’s famed rooftop bars during one of Chicago’s perfect summer days.cocktail-party-552937_1920

Go to Farmers Markets in the Fall

After the leaves change their colors but before sub-zero temperatures arrive, Chicago is full of farmers markets. From fresh fruits to homemade pies, these are some of the yummiest foods in one of the cutest, most fun places to visit in the city before it’s too cold to set food outside.

Photo taken by Paula Satariano

Christkindlmarket in the Winter

Christkindlmarket is the country’s largest Christmas market. Held annually at Daley Plaza, the festival attracts more than 1 million visitors every year. What began as a German tradition has become one of the most popular parts of Chicago. You can find typical German food and drinks, holiday entertainment and gifts, and best of all: admission is free!christmas-market-540918_1920

St. Patrick’s Day in the Spring

Chicago takes St. Patrick’s Day very seriously. The Chicago River is dyed green. There is a St. Patrick’s Day parade through Grant Park and another one south of Hyde Park. Neighborhood bars, restaurants, and shops each have their own unique way of celebrating and decorating. Pub crawls are rowdier. Families take to the local parks to watch the various festivals. Every type of celebration can be found here.


Looking for more to do in Chicago? Visit our website or explore our app to find exclusive hotel deals and fun activities in The Windy City

13 Replies to “The Best Thing to Do in Chicago Each Season

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  2. As the third most populous city in the USA, Chicago has a lot to offer locals and tourists alike. Traveling during the off season is nothing new, but it’s one of the best times to visit the beautiful windy city.

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