Family Road Trip Guide: Chicago, Illinois

The Windy City rolls out a welcome mat woven with fun for families.

From the dazzling architecture to world-class museums and award-winning food, it’s no wonder why Chicago has been voted Best Big City in the U.S. five years in a row by readers of Conde Nast Traveler. While summer in Chicago truly is the best, anytime is a great time to visit with your family. Dance at a festival, sunbathe on a beach, nosh on a rooftop and play at an incredible park all in the same day. Free events, parks and activities can help stretch your budget.

Getting to Chicago

Chicago is roughly a four-hour, 300-mile drive from Detroit. Take I-94 W and/or I-90W depending on traffic.

What Families Love about Chicago

Chicago museums and parks are some of the biggest draws for family visits. Museum of Science and Industry, with a submarine, coal mine and simulated tornado exhibit, puts forward hands-on learning. Roar at Sue the T. rex at the Field Museum. Inspire space exploration at the Adler Planetarium. See sharks, dolphins and beluga whales at the Shedd Aquarium. Play at sensational children’s museums, with the Chicago Children’s Museum at Navy Pier, Kohl Children’s Museum in Northbrook, DuPage Children’s Museum in Naperville and The Children’s Museum in Oak Lawn all worthy of a visit. In particular, Bronzeville Children’s Museum on Chicago’s south side, is the first and only African American children’s museum in the country.

Photo credit: Choose Chicago: Chicago Children’s Museum at Navy Pier

At Navy Pier, take a spin on the Centennial Wheel, watch the night sky light up with fireworks, play Pixar Putt mini golf and dip into a deep dish Giordano’s pizza. Firefighting-loving families will especially enjoy a Chicago Fireboat Tours cruise around the water. Choose from a historical and architectural cruise or a sunset skyline cruise aboard the first diesel-powered fireboat, which was originally in service from 1937-1981.

Millennium Park is always a happening place. Snap photos by “The Bean,” splash in the interactive Crown Fountain that spits water, take in a concert at the Jay Pritzker Pavilion or a free summer film on The Great Lawn. Walk the picturesque stainless steel BP Bridge to Maggie Daley Park for a playground that will blow your children’s minds. Suspension bridges, saucer swings and tube slides entertain kids for hours. There’s also a climbing wall, mini golf and a skating ribbon, which you can rollerblade on in the summer and ice skate on in the winter.

Oak Street Beach, Chicago. Photo credit: Abel Arciniega, @tequilagraphics

Chicago’s 26 miles of scenic lakefront include an 18-mile trail for walking and biking and more than 20 free beaches. North Avenue Beach is usually bumping, with refreshing drinks, sandwiches and skyline views served at Castaways Bar & Grill. Oak Street Beach is walkable from many Mag Mile and Gold Coast hotels. Lincoln Park Zoo, across from North Avenue Beach, is open every day and entry is always free.

Stroll, people watch, sip a drink or munch on casual bites and gelato on the Chicago Riverwalk. You can rent a kayak from Urban Kayaks or an adorable retro boat from Chicago Electric Boat Company for a more memorable way to explore. If sports are your jam, Chicago boasts the Cubs, White Sox, Bulls, Bears, Blackhawks, Wolves, Sky, Fire, Dogs and more. There’s a team to watch every season.

Willis Tower Skydeck. Photo credit: Choose Chicago: Willis Tower Skydeck

Willis Tower Skydeck showcases sensational views and a chance to test your bravery. Stand on the ledge and see how small cars look below. Then immerse yourself in Color Factory Chicago interactive art installations downstairs. TILT is a thrill ride offered at 360 Chicago, in the John Hancock Center. Hold on tight as you’re tilted out 1,000-feet above Michigan Avenue. There’s shopping galore in the Gold Coast, on Michigan Avenue and State Street. American Girl Place is a favorite store for families, with a restaurant and hair salon for dolls.

Check out neighborhoods like Pilsen and Chinatown for a dose of culture and delicious eats.

For something different, visit Prince: The Immersive Experience, which made its worldwide debut in Chicago in June. Take an interactive tour across 10 multidimensional spaces showcasing Prince’s life and music. Dance to Purple Rain, admire Prince’s legendary ruffled shirts and smile for the photo ops.

Where to Stay in Chicago

There are literally dozens of other hotels and airbnbs that accommodate families.

Named the #1 hotel in the U.S. by U.S. News and World Report, The Peninsula Chicago is a five-star accommodation you’ll definitely want to swing for. Conveniently located near the Magnificent Mile. Swim in the indoor pool surrounded by panoramic views of Lake Michigan. Enjoy pastries at afternoon tea in The Lobby restaurant. Kids will get a kick out of playing in a Camp Peninsula in-room tent with camping-themed treats. De-stress at the end of the day with a Revitalization Bath Ritual. Salts, oils and aromatherapy will be set up for you to soak and savor.

The Peninsula Chicago. Photo credit: AdamAlexanderPhoto.com, ©Adam Alexander Photography 2019

Sofitel Hotel Magnificent Mile is a swanky hotel with a French twist, which is especially fun for older kids or those wanting to walk to the lakefront, shopping and dining. Revel in summer’s radiance on La Terrace, where you can delight in French cuisine and creative cocktails. Treat yourself to a room service breakfast of Brioche French Toast and feel like a king or queen in the city.

Where to Eat in Chicago

While in Chicago, you’re going to feel like you should try the deep dish pizza and Chicago-style hot dogs. Superdawg and Portillo’s are awesome spots for hot dogs. Remember to take on all the toppings, but save the ketchup for the fries. You’ll find tons of pizza places, including Lou Malnati’s, Pequod’s, and my personal favorite (also said to be Oprah Winfrey’s favorite thin crust), Pizano’s.

JoJo’s Shake Bar serves those super-indulgent Instagrammable milkshakes with cookies, marshmallows and colorful toppings. Big Star Taco is a must in Bucktown and Wrigleyville. Smoque BBQ is the place to go for barbecue. I’m a huge fan of Chef Stephanie Izard, winner of Top Chef season 4. Her Little Goat Diner is the perfect place to take tiny diners. Safehouse, a spy-theme restaurant, will put kids on a mission to crack a code. Wildberry Pancakes and Cafe is my children’s favorite breakfast spot, but they’d never pass up Stan’s Donuts. For an elevated European-inspired brunch menu, try Cobblestone Restaurant. Pecan Pie French Toast, anyone?

Lou Malnati’s Chicago. Photo credit: Abel Arciniega, @tequilagraphics

Near Lincoln Park Zoo, the Patio at Café Brauer serves up casual lunch, dinner and weekend brunch in a serene pond-side setting with views of the Chicago skyline. Beat Kitchen is my family’s favorite patio on the RiverWalk, serving pizza, tacos and drinks with a DJ in the evenings. For a special, luxurious meal that tickles all the senses, turn to Travelle. The multi-course tasting menu is a symphony of scents, flavors and textures showcasing local produce and the talents of an outstanding chef in an extraordinary setting.

If you have adventurous eaters or you’re able to sneak away for a date night, I suggest Sushi by Bou at the Claridge House hotel. Belly up to the sushi bar and allow the chef to make the most tasty selections in a timed omakase experience, which translates to, “I’ll leave it up to you.” Every tasting will be different, based on what’s fresh at the time, but the black cod with miso paste in seaweed paper is my favorite.

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