Planning your next vacation? Think about world-class Chicago for a fabulous and memorable getaway. Outstanding museums, spectacular restaurants and a host of exciting venues are just waiting to welcome you. Discover these unique attractions and favorite gems during your stay.
Hop Aboard a Wendella River Cruise
One of the best ways for a great perspective of the entire city is to take a cruise on a Wendella Architecture Tour. Choose from 45 or 90-minute cruises along the Chicago River for a true sense of history and place throughout Chicago’s 130 years of architectural innovation. Explore three different parts of the Chicago River as well as pass by distinct neighborhoods that define the skyline with structures built from 1920 to 2020. Learn about more than 80 diverse buildings and bridges as well as the famous architects who designed them. Many older buildings along the river have been repurposed. Once empty factories have been turned into the city’s hottest condos. You’ll come away more than impressed by the dynamic vision of the city builders. On a hot summer day, you’ll love being out on the water!
When you’re done, walk on over a few blocks to Millennium Park and snap a few selfies at “Cloud Gate,” Chicago’s stainless steel sculpture better known as “The Bean.”
Spend the Night in a Museum Hotel
Photo courtesy of 21C Museum Hotel
Ever wonder what it’s like to sleep in an art museum? Check into the new 21C Museum Hotel, conveniently located just steps away from the iconic North Michigan Avenue and find out. The 4-star 21C Museum Hotel is within easy walking distance of everything. Explore two stories of contemporary art featuring sculpture, tapestries, photographs and paintings Free and open 24/7, this historic 21c Museum actually brings a new cultural resource to Chicago’s fascinating art scene. Enjoy all of 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. 21C Hotels are known for their signature Evergreen penguins that (pre-Covid) could be found in the halls, in your room or even your shower! You never know when one is going to pop up! The entire experience evoked a real sense of inspiration and relaxation.
Visit the New Monet and Chicago Exhibit
The impressive Art Institute is a world-class institution that must be included in your visit and there’s always something new to see. Currently on display is “Monet and Chicago,” featuring more than 70 works of the artists’ paintings and drawings. The exhibit traces the history of the French Impressionist and his relationship with the city that started in 1888. Seeing these still lifes, figural scenes, seascapes, and landscapes up close is a thrill you don’t want to miss, through June 14. Their other new exhibit is the fabric portrait quilts of Bisa Butler demonstrating colorful and cultural memory. Through September 6.
Relive Your Favorite “Friends” Episodes
“The Friends Experience – The One in Chicago” puts fans front and center of the popular TV show through an interactive 2-story experience. Walk into 12 nostalia-filled rooms that bring back the memories through 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 the perfect place for all of your Instagram moments!
Immersive Van Gogh Creates New Imagery
No trip to 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 famous 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 classical and contemporary music. too. Stand in one of the circles on the main floor, then step up to the balcony for a higher perspective. Through September.
Chicago’s Crime Tour Makes History Come Alive
Almost as famous as Michael Jordan are the reputations of most-wanted criminals, John Dillinger and Al Capone. Get a behind-the-scenes look with stories about America’s original crime legends on this 2-hour tour from Chicago Crime Tours. Hop on and off the bus where the real events took place, like the Biograph Theatre where Dillinger met his fate, see videos of the historic events and get the real scoop. We followed along as Elise, our enthusiastic guide, shared her vast knowledge of Chicago history. You’ll come away knowing “crime doesn’t pay!” Chicago Crime Tours also offers Night Crime Tours, too.
In Chicago, dining is an experience to be savored. From mouth-watering steaks to ethnic cuisine to brunch and more, Chicago offers an abundance of outstanding restaurants.
Dig In to Deep Dish Pizza Tours
If you’ve done a food tour in other cities, you know they let you sample a variety of different menu items as well as offer an outstanding value. Now try the Deep Dish Pizza Tour, Chicago’s newest entry into the foodie tours. The Finger Licking Deep Dish Pizza Tour is created by Don Contursi, also 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. Choose your time between between 11 am – 6 pm every day for your two-hour stairway to pizza heaven! Start off at Gino’s East, then head to Pizzeria Uno and end at Lou Malnati’s. You’ll also appreciate the walk through Chicago’s most popular areas. When you enter the pizzaria, you’ll get seated quickly and dig into fresh hot pizza without the typical wait, usually in just 10 minutes. At each stop, you’ll enjoy one of their Signature Deep Dish Pizzas, topped with ½ cheese, ½ sausage or veggies. With the optional beverage package, you can pair your pizza with a local Chicago beer at each stop. Best part, you can take the leftovers back home. Look for more Finger Licking Foodie Tours coming soon.
Big Portions, Big Taste at Eleven City Diner
This traditional eatery located in Printer’s Row (a National Historic District) 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 and hands down, Eleven City Diner is the best deli in the whole city. Bigger really is better. So, grab breakfast all day, try his home brew Root Beer, slurp homemade malts and shakes, enjoy smoked meats in a sandwich stacked like Willis Tower, and taste matzoh balls the size of baseballs. Try Rubin’s Reuben or Moshe Cristo, build your own Dip Box, or savor a Brooklyn Egg Cream (the Chocolate Phosphate as they call it in Chicago), along with oversized potato pancakes and ginormous desserts. Save room for their carrot cake. The atmosphere is warm, friendly and inviting and you’ll feel right at home. Dine in, pick up, or delivery.
Enjoy American Fare at Bernie’s
Named after Chef Zack Sklar’s grandfather, Bernie’s opened in Chicago in 2015, a part of the Peas & Carrots restaurant group from Michigan. Serving an American-style menu with a twist, Manager Donna Gomez told me the chef draws on flavors from Spain to coastal Italy and Provence. 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. Recommended are the braised short ribs with heirloom carrots, asparagus, polenta and mushroom sauce. Or try the glazed salmon that was rich and savory. Head up to their seasonal rooftop patio for great views while you dine.
Indulge in Gibsons Bar and Steakhouse – The Ultimate Chicago Dining Experience
Photo courtesy of Gibsons Steakhouse
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 steak to choose from? Go 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.
R.J. Grunts Celebrates 50th Anniversary
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 visitors and locals, too. We were escorted through the Gold Coast, South Loop and Lincoln Park with friendly, knowledgeable guides. Enjoy a free 2-4 hour visit 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. Make that a stop on your itinerary!
Click this link to plan your own Chicago vacation. The Windy City is waiting to welcome you.