Chicago is an amazing city to explore solo—full of vibrant neighborhoods, iconic landmarks, and incredible food. Whether you’re taking in the skyline views, indulging in top-tier dining, or finding time for fitness and self-care, this itinerary has you covered.
Day 1: Rooftop Views & Cozy Eats
- Check-in & Settle In – Choose a centrally located hotel like The Hoxton, The Pendry, or LondonHouse for easy access to all the main spots.
- Sunset Cocktails at Cindy’s Rooftop – Kick off your trip with a cocktail at Cindy’s Rooftop, an open-air terrace with stunning views of Millennium Park and “The Bean” (Cloud Gate). Try their signature gin-based cocktail and soak in the scenery.
- Dinner at Mojo – Head to Mojo for a casual but flavorful dinner. Their grilled chicken is a must-try, and don’t skip their fresh-baked cookies for dessert.
Day 2: Exploring & Cozy Tavern Vibes
- Morning Workout at FP Movement Studio – Start your day with a workout class at FP Movement Studio, a stylish fitness space with energizing group workouts.
- Lunch at Cira (The Hoxton Hotel) – After freshening up, enjoy Mediterranean-inspired dishes at Cira, a chic restaurant in The Hoxton Hotel. Their hummus, grain bowls, and creative small plates are perfect for refueling.
- Explore Downtown Chicago – Walk along the Chicago Riverwalk, check out The Art Institute of Chicago, or just wander through the city’s stunning architecture.
- Dinner at Trivoli Tavern – End the day at Trivoli Tavern, a cozy yet upscale tavern in Fulton Market. Their Vodka Rigatoni is rich, creamy, and the ultimate comfort food.
Day 3: Sky-High Views & Shopping on Mag Mile
- Morning Workout at FP Movement Studio – Another great start to the day with a workout!
- Skydeck at Willis Tower – One of Chicago’s most iconic attractions! Take in the breathtaking views from Skydeck Chicago at Willis Tower, and if you’re feeling brave, step onto The Ledge—a glass balcony extending 1,353 feet above the city.
- Starbucks Reserve Roastery – Head to the largest Starbucks in the world, located on Michigan Avenue. Try their pastries and the espresso martini flight for a mid-morning pick-me-up.
- Shopping on The Magnificent Mile – Spend the afternoon exploring The Mag Mile with stops at high-end boutiques, local shops, and department stores like Nordstrom and Neiman Marcus.
- Dinner at Cabra – For a lively dinner, Cabra at The Hoxton is the place to be. Their Chicken Anticuchos and Papas Huancaína paired with a Pisco Sour offer the perfect Peruvian-inspired meal.
Day 4: Yoga in the Sky & Farewell Coffee
- Yoga at 360 Chicago – Start your last morning with Yoga in the Sky at 360 Chicago, located in the John Hancock Building. Flow through a class with panoramic views of the city below.
- Coffee & Croissant at Ralph’s Coffee – Before packing up, grab a coffee and croissant from Ralph’s Coffee (inside Ralph Lauren on Michigan Avenue), known for its cozy yet refined ambiance.
- Pack Up & Head Home – After an unforgettable solo trip, it’s time to head home with plenty of great memories (and maybe a few shopping bags).
Additional Things to Do (If You Have Extra Time)
- Chicago Architecture Boat Tour – A must for first-time visitors! Cruise along the Chicago River while learning about the city’s rich architectural history.
- Lincoln Park & The Conservatory – If you love green spaces, take a peaceful walk through Lincoln Park and explore the stunning Lincoln Park Conservatory.
- Museum of Contemporary Art – A great stop for modern art lovers, featuring ever-changing exhibits and thought-provoking installations.
- Try Deep Dish Pizza – If you haven’t already, grab a slice of deep-dish pizza at Lou Malnati’s, Giordano’s, or Pequod’s before you leave.
Final Thoughts
This Chicago itinerary is perfect for a solo traveler looking for the right mix of adventure, relaxation, and indulgence. Whether it’s sky-high views, trendy dining spots, or simply strolling through the city, Chicago is full of unforgettable experiences.