Staycation Ideas: 12 Things to Do On a Staycation in Chicago

Taking a staycation in your own city offers tons of uplifting and memorable experiences. Hang out in Chicago like a tourist and come away with a fresh perspective of the city you call home. If you are looking for creative ways to spend your time, we have compiled a list of staycation ideas in Chicago.


Start On the River

See Chicago’s architectural jewels from the water. Cruise on a Wendella Architecture Tour for a true sense of history and place in Chicago’s 130 years of design innovation. Captain Craig Wenokur told us the best description of Chicago’s architecture is really diversity, creating a skyline with structures built from 1920 to 2020. Many older buildings along the river have been repurposed. Once empty factories have been turned into the city’s hottest condos. If you are taking a staycation in Chicago, sign up for a 45 – 90 minute Chicago River Architecture Cruise and you’ll be impressed by the dynamic vision of the city builders.  And you’ll love being out on the water!

Photo courtesy of 21C Museum Hotel

Sleep in a Museum

As a guest at two other 21C hotels, I was primed to enjoy their newest Chicago location. Conveniently located just steps away from Michigan Avenue, the 4-star 21C Museum Hotel is within easy walking distance to everywhere! Here, you’ll be surrounded by two stories of contemporary art featuring sculpture, tapestries, photographs and paintings that create a hip vibe. Free and open 24/7, the historic 21c Museum actually brings a new cultural resource to Chicago’s vast art scene.


But it’s the elegant details, unique amenities like the Nespresso coffee maker, Malin & Goetz bath luxuries and bathroom fixtures that made staying at the 21C such a joyful experience. The bed was uber-comfortable and the bedding exquisite, matched only by the expansive views of the city. What’s really funky is their signature Evergreen penguins that (pre-Covid) could be found in the halls, in your room or even your shower! The entire experience evoked a real sense of inspiration and relaxation.

Read More: 5 Popular Vegetarian & Vegan Restaurants to Visit in Chicago


Visit the New Monet and Chicago Exhibit

No matter how many times you’ve been to the Art Institute, there’s always something new to see. Featuring more than 70 works of art, Monet and Chicago traces the history of the French Impressionist and his relationship with the city that started in 1888. If you’re searching for activities to try on a staycation in Chicago, see these masterpieces up close through June 14. Their other new exhibit is the fabric portrait quilts of Bisa Butler demonstrating colorful and cultural memory. Through September 6.

Photo courtesy of The Friends Experience

Be Friends With “Friends” 

“The Friends Experience – The One in Chicago” puts fans front and center of the  popular TV show through an interactive 2-story experience. Have serious fun as you explore 12 nostalia-filled rooms that bring back the memories featuring video clips, larger-than-life photographs, props, costumes and more. Step inside Joey and Chandler’s apartment, Rachel and Monica’s kitchen and Central Perk where you’ll find everything “Monica clean.” This is Instagram bliss at its best! 


Read More: Top 6 Chicago Wedding Photographers to Hire For Your Special Day

Photo courtesy of Choose Chicago

Go Digital at Immersive Van Gogh 

No vacation in Chicago is complete without a visit to the new Immersive Van Gogh, a visually spectacular digital art exhibition that invites audiences to “step inside” the iconic works of post-Impressionist artist Vincent Van Gogh. Through art, light, music and movement, the experience envelops your visual and audio senses. Get immersed in the music, too with Edith Piaf’s “No Regrets.” Stand in one of the circles on the main floor, then step up to the balcony for a higher perspective.


Grab a Seat on Chicago’s Crime Scene Tour

Almost as famous as Michael Jordan is the reputations of most-wanted criminals, John Dillinger and Al Capone. Get all the deets on America’s original crime legends on this 2-hour tour. Hop on and off the bus where the real events took place, see videos of the historic events and find out what really happened. Elise, our guide was knowledgeable and enthusiastic, making  the stories come alive. You’ll come away knowing “crime doesn’t pay!” Chicago Crime Tour also offers Night Crime Tours, if you dare!


Dining Divine!

As a Chicagoan, you know dining is an experience to be savored.  From mouth-watering steaks to ethnic cuisine to brunch, there are plenty of restaurants to attend on a staycation in Chicago with outstanding food. Here’s the buzz.


Go Deep! 

Chicago’s newest entry into the foodie tours is Finger Licking Deep Dish Pizza Tours. Created by former Chicagoan Don Contursi, founder of Finger Licking Foodie Tours of Las Vegas, the self-guided Deep Dish Pizza Tour includes three of Chicago’s most iconic pizza landmarks.  Schedule between 11 am – 6 pm for your two-hour stairway to pizza heaven!

Get seated quickly and dig into fresh hot pizza in just 10 minutes. Start at Gino’s East, then walk to Pizzeria Uno and end at Lou Malnati’s for a Signature Deep Dish Pizza, topped with ½ cheese ½ sausage or veggies. With the optional beverage package, pair your pizza with a local Chicago beer at each stop. Best part, you can take the leftover pizza from your staycation home. Look for more Finger Licking Foodie Tours coming soon.

Eleven City Diner Delivers On Oversize Everything! 

This eatery takes deli to a whole new level. Founder Brad Rubin opened Eleven City Diner about 15 years ago with a single mindset – to do it his way. The results are in — slam dunk, the best deli in the whole city. Grab breakfast all day, try his home brew Root Beer, slurp homemade malts and shakes, see smoked meats in a sandwich stacked like Willis Tower, matza balls the size of baseballs, oversized potato pancakes, and ginormous cakes. The atmosphere is warm, friendly and authentic. Dine in, pick up, or delivery. If you haven’t been, high tail it over to Eleven City Diner and see for yourself.

Get Casual and Creative at Bernie’s 

I had an Uncle Bernie and he would have loved this place. Named after the owner’s grandfather, Bernie’s is a part of the Peas & Carrots restaurant group, Chicago’s first opening in 2015. Serving an American-style menu with a twist, Bernie’s most popular dishes are their burgers and ground lamb hummus, all locally sourced. We started with the fresh kale salad that was chock-full of apples, almonds and quinoa. Dine on the braised short ribs with heirloom carrots, asparagus, polenta and mushroom sauce. Or try the glazed salmon that was rich and tasty. Head up to their seasonal rooftop patio for great views while you dine.

Photo courtesy of Gibsons Steakhouse

Indulge in Gibsons Bar and Steakhouse – The Ultimate Chicago Dining Experience

Hope you’re hungry because Gibsons has been Chicago’s go-to place for USDA prime angus steaks going on 23 years. This intimate iconic restaurant serves up fabulous steaks, seafood and classic cocktails, coupled with unsurpassed attention to details that makes it such a spectacular dining experience.

Which steaks do you choose from? I went with the New York Strip, masterfully grilled to perfection with just the right amount of seasoning. Tasty sides included yummy double-baked potato and creamed spinach. My husband opted for the Pan Seared Alaskan Halibut with asparagus pesto. We splurged, calorie-wise, on the luscious Carrot Cake, with more than enough to take home.

Hang Out at R.J. Grunts

This is Chicago’s first date place, celebrating its 50th anniversary in June. Still known for its awesome burgers, giant hand-scooped milk shakes and the city’s first salad bar, R.J. Grunts was Richard Melman’s original eatery that launched a restaurant empire, Lettuce Entertain You. Try the Tuna Melt Trio plate which was enormous with crisp fries. Or the Grunt Burger with fried onions and bleu cheese that continues to delight. Manager Ron Forsman told me some 20 years ago, the company wanted to shut Grunts down and the outcry from the neighborhood was so intense, they decided to keep it open. Lucky us. Come enjoy all that Grunts is famous for in the heart of Lincoln Park.

Let Chicago Greeters Show You Around

Get up close and personal with Chicago neighborhoods through Chicago Greeters, now available for locals, too. We were escorted through the Gold Coast, South Loop and Lincoln Park with a friendly, knowledgeable guide.  Enjoy a free 2-4 hour tour on your staycation based on your choice of neighborhoods and interests. Register at least 10 days in advance.  Or, check out an Insta-Greeter for an hour-long walk of downtown. Guide Judith Robinson showed us around the Gold Coast, with its art-deco architecture, well-maintained buildings and million-dollar homes. One gem was Restoration Hardware in the historic Three Arts Club, which featured six floors of home furnishings and a gorgeous café setting.  Rush on over, ASAP.

To plan your own Chicago Stay-Cation, go to

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