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Top Five Things to Do in Chicago

This blog post was updated on August 23, 2018.

Planning a trip to the windy city? Whether you’re strolling along the iconic Michigan avenue, grabbing a cup of coffee in the charming Lincoln Park neighborhood or grabbing a slice of pizza in the west side Italian enclave, you’re sure to find something to love about Chi-town.

1. Take a walk down Michigan Avenue : Some of Chicago’s most impressive sights are located along this majestic street the Art Institute of Chicago (which houses an impressive collection of international art from a variety of periods), Millennium Park (home to the famous “bean” metal sculpture), and the Magnificent Mile (a stretch full of swanky shops, restaurants and bars). Michigan avenue also extends into Streeterville (home of the Navy Pier and the Museum of Contemporary Art).

2. Browse the eclectic boutiques in Lincoln Park : This north side community is known for its commitment to local, independent businesses including great clothing, accessory and home goods shops, coffee shops, wine bars and restaurants.

3. Take an architectural boat tour : A lake or river (or combination) architectural boat tour is a great way to see the city from a different perspective.  An experienced guide will point out some of the most impressive architectural sights in the city while you sip on a cup of coffee or a cocktail (depending on the time of day). Boat tours run from the spring until late fall (November). The largest bout tour companies are Wendella Boat Tours ( )  and  Chicago Cruise Lines (

4. Have lunch or dinner in Little Italy : If you’re craving mostaccioli, a calzone or a delicious slice of pizza, head to Little Italy (located on Chicago’s west side). Be sure to grab some sweets at one of the area’s amazing bakeries to take back to your hotel room for breakfast.

5. Groove the night away in a jazz club : A veritable jazz mecca, Chicago is home to some of the greatest jazz clubs in the U.S. Spots like Andy’s Jazz Club (,  The  Joynt  and Clubb Bluejazz (  attract some of the best musicians on the tour circuit today.


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