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Each person’s bucket list is different, as is each person’s definition of a great vacation. Some might only need a weekend away to see a city, while others want to go on a month-long adventure. But one thing’s for sure, every city has amazing places you might have overlooked. That’s why we think staycations are the perfect way to see your city from a new point of view…there are hidden gems waiting to be discovered. Explore ideas why a Chicago Staycation should be on your list for your next getaway.

Chicago staycation

On that note, let’s take a tourist’s eye view of Chicago. The Windy City has always been one of the best staycation cities in the country, and here are 13 reasons why:

Things to Do In Chicago

Millennium Park

Perhaps most famous for its iconic Cloud, Millenium Park is nonetheless a perfect stop for Chicago natives. Like Central Park in Manhattan, Millenium Park most likely has a corner or two you haven’t seen. It’s a mecca of famous architecture and landscape design, and also offers hundreds of free programs throughout the year, including concerts, exhibitions, tours and family fun.

Things to Do in Chicago: Chicago cloud gate

Navy Pier

A famous Chicago landmark, the Navy Pier is one of the most important civic landmarks in the U.S. Each day, different activities are scheduled for the entire family, including, movies, seasonal events and rides.  The People’s Pier is home to the Chicago Shakespeare Theater, Chicago Children’s Museum, the AMC Navy Pier IMAX Theatre, dining and more. 

Chicago Navy Pier

John Hancock Observatory

The website name is for a reason. The 1,000-foot observation deck gives visitors the best views at the best location. A recent addition is the Tilt attraction, which allows visitors to step onto an enclosed platform that extends from the building at a 30-degree angle.

Architecture River Cruise

Just as Boston is famous for its amphibious duck boats, Chicago is famous for its architectural cruises run by Chicago’s First Lady Cruises. These “90 Minutes of Amazing” cruises take visitors around the lake, where they learn about the architectural design of over 50 historic buildings.

Where to Eat in Chicago

Gino’s East

With four locations near the water in downtown, Gino’s East has some of the most famous pizzas in town. Their legendary deep dish pizza is some of the best in the nation. They even have their own blog! What a hip, unpretentious pizza place.

Photo Credit: Gino's East
Photo Credit: Gino’s East


Featuring 13 prime locations, catering, and a bake shop, Rosebud is one of the best-known diner-style chains in the Windy City. And easily one of the tastiest. Even better, you can order everything on their menu online (for pickup).

676 Restaurant & Bar

If you’re looking for a place to eat with unparalleled views of the Magnificent Mile, this American bistro is the perfect spot. Chef is known for using the freshest ingredients from the Midwest and local farmers whenever possible. He even grows a lot of the organic produce on the rooftop gardens located on the sundeck at the Omni Chicago Hotel. This unique restaurant experience is one you won’t want to miss.

676 Restaurant Chicago


A fancy Italian restaurant with a grassroots bent, Eataly not only features famous food, it also loves contributing to local causes. Take their “Nose to Tail” initiative, in which they promise to buy animals from local farmers once a week, for example. Or their “The Many Shades of Truffles” bar, which will be America’s first truffle bar. Pretty cool stuff.

Signature Room

At the top of the John Hancock Center, the Signature Room offers a dazzling skyline view, warm wood and art deco, and 360 degree views of the city. It’s the perfect place for special occasions.

Photo Credit: Haute Living
Photo Credit: Haute Living


Where to Shop in Chicago

Michigan Ave

Called “The Magnificent Mile” by some, Michigan Ave. is a hotbed of boutique variety and touristy abundance. No matter who you are or what you’re looking for, you’re likely to find something you want on Michigan Ave. Check out its homepage for details.

Chicago Magnificent Mile

Water Tower Place

Water Tower Place is ideally situated between the Museum of Contemporary Art (MCA) and the John Hancock Center for a full day’s adventure. With 758,000 sq ft and 74 floors of shops and restaurants, everyone will find something they love.

The Shops at North Bridge

For more conventional shoppers, North Bridge is an all-American shopping complex that includes over 50 stores as well as a Nordstrom’s and Eataly. Oh, and there are 20 other restaurants in fewer than 6 city blocks, for good measure.

Photo Credit: USA Today
Photo Credit: USA Today

Nike Town

One of the largest Nike stores in the world, Nike Town is a 5-story wonderland for sports apparel aficionados. The 1st floor is what’s in, the 2nd floor is devoted to football and soccer, the 3rd floor to crossfit, the 4th floor to women’s apparel and running shoes, and the 5th floor to kid’s apparel and a “design your own shoe” station.

Where to Stay in Chicago

Located in the heart of the city, the beloved Omni Chicago Hotel is right in the middle of all the local attractions. You’ll be within walking distance to all the parks, museums, shops, and music venues. Take a stroll along the beautiful lakefront, then come back to your hotel and have a nice glass of wine at the 676 Bar and Lounge. Which was recently named one of the Top 10 Hotel Bars in Chicago by Michigan Avenue Magazine. The Omni Chicago Hotel is celebrating its recent renovation and is proud of its newly appointed guest suites, including 10 specialty suites.

Where to Stay in Chicgao: Omni Chicago Hotel