Five Things You Must Do in Chicago

Posted by Tina in Chicago, Illinois, Top 5

Arguably one of Illinois’ most popular destinations, Chicago (a.k.a. the “Windy City”) is instantly recognizable with its sky-scrapped silhouette.  Rich tradition and diversity are also intertwined in the city’s flair for all things culinary. World famous pizza, top chefs and cuisine from seemingly every corner of the globe all have a spot at the table Chicago sets. Check out some of our favorite can’t-miss attractions from the Second City.

1. “The Bean”

Chicago’s famous Cloud Gate art installation — known as “The Bean” — adorns the city’s skyline. It was inspired by liquid mercury and is a popular tourist attraction. You’ll have to fight your way through the crowds of tourists who are always there, but regardless, it’s a Chicago staple!

2. The Chicago St. Patrick’s Day Parade

From raucous pub crawls to lively parades and family-friendly festivals, there is no doubt about it: There’s nothing quite like St. Patrick’s Day in Chicago. Chicago’s downtown parade occurs on the Saturday before St. Patrick’s Day, beginning with the dyeing of the Chicago River at 9am and continuing in Grant Park with a parade at noon. Between the neighborhood festivities, downtown river boat tours and Celtic performances, there is no shortage of ways to celebrate.

3. Oz Park

Oz Park is one of Chicago’s hidden gems. It’s completely Wizard of Oz-themed, with statues of all the major characters. And while the famous green villain doesn’t get her own statue in the park, you can find Dorothy sporting her ruby slippers!

4. The Wieners Circle

The Wieners Circle is famous for Chicago-style hotdogs, cheese fries and burgers. But be careful — you can expect a little verbal abuse from the employees (all in good fun.) The restaurant is open until 5 a.m. which makes it the perfect place to satisfy those late-night munchies.

5. Navy Pier

Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It holds more than fifty acres of parks, gardens, shops, restaurants, family attractions and exhibition facilities and is the top leisure destination.

And don’t worry — Tripbound has your room accommodations covered. The Wyndham Grand Chicago Riverfront is set against the Chicago River, just steps from the famed cultural district simply known as “The Loop.” This hotel uniquely positions you to enjoy the best the city has to offer.

Contact a Tripbound travel coordinator to book your Chicago vacation rental today! Call us at 1.888.816.5214 or visit us online at

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