Chicago: The Ultimate Urban Adventure

Discover, Dine & Explore While Destination Sitters Takes Care of the Kids! 

Welcome to Chicago, a city where world-class dining, stunning architecture, vibrant arts, and outdoor adventures come together. Whether you’re here to soak in skyline views from the Willis Tower, experience the rich jazz and blues scene, take an architecture cruise, or indulge in Michelin-starred cuisine, the Windy City offers something for every traveler. With Destination Sitters, you can explore worry-free while we provide trusted, professional childcare! 

Chicago is known for its skyline, historic neighborhoods, and cultural richness. 

Must-See Attractions 

• Millennium Park & The Bean (Cloud Gate) – Take a classic Chicago selfie at this stunning reflective sculpture. 

• Willis Tower Skydeck (Formerly Sears Tower) – Step onto The Ledge, a glass balcony 103 stories above the city. 

• Navy Pier – Ride the Centennial Wheel, enjoy fireworks, and explore restaurants along Lake Michigan. 

• Chicago Riverwalk – Stroll along the river for cafés, live music, and incredible skyline views. 

• The Art Institute of Chicago – A world-class museum featuring Van Gogh’s “The Bedroom” and Grant Wood’s “American Gothic”. 

Where to Eat Nearby (4 & 5-Star Picks) 

• Alinea – Chicago’s only three-Michelin-star restaurant, offering a theatrical multi-course dining experience. 

• Ever – A two-Michelin-star restaurant with an artistic, seasonal tasting menu. 

• Gibsons Bar & Steakhouse – A classic Chicago steakhouse, loved by locals and celebrities. 

Chicago’s lakefront location offers stunning views, outdoor activities, and water excursions. 

Best Waterfront Experiences 

• Chicago Architecture River Cruise – One of the best ways to explore the city’s stunning skyline and historic buildings. 

• Lake Michigan Sunset Cruise – Sail into the evening with dazzling skyline views and champagne. 

• Kayaking on the Chicago River – Paddle past iconic skyscrapers and historic bridges. 

• Oak Street Beach – A relaxing lakeside spot perfect for sunbathing and people-watching. 

🎟 Pro Tip: Book a private yacht rental for an exclusive Chicago River or Lake Michigan experience! 

Where to Eat Nearby 

• Shaw’s Crab House – Chicago’s best seafood spot with oysters and crab legs. 

• RPM Italian – A chic, modern Italian eatery co-owned by celebrity couple Bill & Giuliana Rancic. 

Despite being a big city, Chicago is home to beautiful parks, scenic trails, and outdoor escapes. 

Best Outdoor Activities 

• Lincoln Park & Lincoln Park Zoo – A free, family-friendly zoo and park with stunning gardens. 

• The 606 Trail – A converted rail line offering a scenic walking and biking path through hip neighborhoods. 

• Maggie Daley Park – A massive urban park featuring a climbing wall, rollerblading paths, and a winter ice skating ribbon. 

• Garfield Park Conservatory – One of the largest botanical conservatories in the country, featuring lush indoor gardens. 

Where to Eat Nearby 

• North Pond – A farm-to-table fine dining restaurant nestled within Lincoln Park. 

• Avec – A casual but critically acclaimed Mediterranean-inspired eatery. 

Chicago is a cultural powerhouse, from world-renowned theaters to iconic blues and jazz clubs. 

Best Arts & Music Experiences 

• Chicago Theatre – See a Broadway-caliber production in a historic, beautifully restored venue. 

• Buddy Guy’s Legends – A must-visit for live blues music in the home of the blues. 

• Second City Comedy Club – The famous improv club where comedians like Tina Fey and Steve Carell got their start. 

• Goodman Theatre – One of Chicago’s premier theaters featuring award-winning performances. 

🎟 Pro Tip: Book a VIP backstage tour at the Chicago Theatre or a front-row table at a jazz club for an unforgettable night! 

Where to Eat Nearby 

• Oriole – A two-Michelin-star tasting menu experience. 

• Girl & the Goat – A trendy, globally inspired eatery from celebrity chef Stephanie Izard. 

Chicago offers everything from high-end designer boutiques to unique local markets. 

Best Shopping Destinations 

• The Magnificent Mile (Michigan Avenue) – Home to Gucci, Burberry, Neiman Marcus, and more. 

• Oak Street – A luxury shopping district featuring exclusive designer brands. 

• Andersonville & Wicker Park – Known for local artisan boutiques, vintage shops, and independent bookstores. 

Where to Eat Nearby 

• The Purple Pig – A Mediterranean-inspired eatery with a cult following. 

• Bavette’s Bar & Boeuf – A classic steakhouse with a speakeasy vibe. 

Chicago’s food scene is legendary, featuring everything from deep-dish pizza to Michelin-starred tasting menus. 

Must-Try Restaurants 

• Pequod’s Pizza – A local favorite for caramelized-crust deep-dish pizza. 

• Monteverde – One of the best Italian restaurants in the country, featuring handmade pasta. 

• Smyth – A fine dining experience blending modern American flavors with artistic plating. 

🌅 Dinner with a View? Try Cindy’s Rooftop for stunning Millennium Park views. 

After exploring the city, unwind with luxurious spa treatments and wellness escapes. 

Best Spa & Wellness Retreats 

• The Spa at The Peninsula – A five-star luxury spa with skyline views. 

• AIRE Ancient Baths – A stunning, candlelit bathhouse inspired by ancient Roman and Greek traditions. 

• Waldorf Astoria Spa – An intimate, high-end spa experience in the Gold Coast. 

Chicago is a perfect city for couples, offering romantic rooftop bars, candlelit dinners, and lakeside strolls. 

Most Romantic Experiences 

• Sunset Cocktails at The Signature Lounge (John Hancock Tower) – Sip cocktails 96 stories above the city. 

• Private Gondola Ride on the Chicago River – Experience a Venetian-style boat ride under the city lights. 

• Helicopter Tour Over Downtown Chicago – See the skyline and Lake Michigan from above. 

💍 Planning a Wedding or Honeymoon? The Drake Hotel and LondonHouse Chicago offer stunning venues with historic elegance. 

• Best Time to Visit: Spring (April-June) and fall (September-October) for ideal weather. 

• Time Zone: Central Standard Time (CST). 

• Getting Around: CTA (L-Train), Uber/Lyft, and walking make exploring easy. 

• Airport: O’Hare International Airport (ORD) and Midway Airport (MDW) – Both offer easy access to downtown. 

Plan Your Chicago Adventure Today! 

While you explore, Destination Sitters provides trusted, professional childcare, so you can experience the Windy City worry-free! 

👶 Trusted & Fully Vetted Babysitters – All sitters undergo a background check, are CPR-certified, and are personally interviewed. 
🧩 Custom Babysitting Services – Whether you need care for a wedding, conference, date night, or event, we tailor our services to your needs. 
🎨 Engaging & Fun – Our sitters bring age-appropriate toys, crafts, and games to keep kids entertained while you relax.