Chicago brims with extraordinary experiences that locals often overlook. The Windy City’s historic boutique hotels and secret rooftop pools create countless opportunities for memorable staycation adventures.
The city’s finest staycation hotels blend luxury stays with local charm. Chicago’s diverse neighborhoods set perfect backdrops for memorable local getaways. Couples can plan romantic escapes, families can enjoy kid-friendly activities, and anyone can squeeze in a quick day trip.
We’ve gathered 10 must-try staycation experiences that highlight Chicago’s hidden gems in 2024. These carefully chosen activities turn ordinary days into extraordinary adventures. The best vacation spots might be closer than you think – right here at home.
Discover Hidden Luxury Retreats
Chicago’s architectural treasures hide luxury retreats that make staycations as exciting as traveling abroad. The city’s finest getaways combine historic charm with modern luxury to create unforgettable Chicago adventures.
Boutique Hotels in Historic Buildings
The Chicago Athletic Association, set in a beautiful 1890s monument, has transformed from an exclusive club into one of Chicago’s best staycation spots. The property keeps its Venetian Gothic architecture while adding modern luxury amenities and stunning views of Millennium Park.
The Gwen sits in the historic McGraw-Hill Building and captures Chicago’s 1930s glamor with a modern touch. The hotel’s status as a sculptural masterpiece makes it perfect for couples who want both history and luxury during their Chicago stay.
Unique Spa Experiences
The Peninsula Spa & Wellness Center sits on the 20th floor and creates a peaceful urban escape with treatments that draw from Ayurvedic and Asian philosophies. Guests can enjoy:
- Half-Olympic length swimming pool with floor-to-ceiling windows
- Relaxation lounge with fireplace
- Steam rooms and private treatment suites
- Yoga room and fully equipped fitness center
AIRE Ancient Baths creates a distinctive Chicago experience in an updated River West factory space. You’ll find indoor and outdoor baths, aromatherapy steam rooms, and special treatments including their signature red wine soak.
Rooftop Pool Escapes
The city’s high-rise pools give amazing views of the skyline. The Viceroy Chicago features an 18th-floor rooftop pool that overlooks Lake Michigan and the Gold Coast district. Soho House Chicago has a steel-rimmed rooftop pool with comfortable loungers that’s perfect for a summer day trip.
The Hoxton in the buzzing Fulton Market pairs its seasonal rooftop pool with Cabra, a Peruvian-inspired restaurant. This combination creates a perfect spot for relaxation and great food. The hotel welcomes both overnight guests and day visitors with its “open-house policy”.
These luxury hideaways show why a Chicago staycation can be just as exciting as traveling somewhere else, with world-class amenities just minutes from home.
Explore Cultural Immersions
Chicago’s museums and galleries give art lovers a chance to connect with the city’s artistic heritage. These personal cultural experiences make great additions to any Chicago staycation plan.
Behind-the-Scenes Museum Tours
The Art Institute of Chicago’s private VIP tours let you access one of the world’s largest art collections. Expert docents guide visitors through the largest collection of Impressionist artwork outside the Louver. They share untold stories behind famous masterpieces. Art enthusiasts can skip the lines and see major works with knowledgeable guides who tailor the experience to their interests.
The Museum of Contemporary Art features intimate 50-minute private tours that bring exhibitions to life. Groups can schedule exclusive viewings before or after public hours. These tours create memorable Chicago staycation moments.
Private Art Gallery Experiences
Art Encounter takes you behind the scenes of private collections and artist studios. Their expert guides lead interactive talks with collectors and artists. You’ll get rare glimpses into the art world that most people never see. Couples on a Chicago staycation will love these special cultural experiences.
Local Artist Workshop Sessions
The city’s thriving artistic community welcomes you into creative spaces. Chicago Park District’s cultural centers offer programs such as:
- Art classes in many mediums
- Music and dance instruction
- Special events with local artists
Lillstreet Art Center, a 48-year-old institution, welcomes artists at every skill level. Families on a Chicago staycation can explore their creative side together here. The center gives both beginners and professionals space to work, so everyone finds their place.
Local studios offer personal creative sessions too. Indigo & Violet Studio focuses on craft workshops and creative parties. Small groups can enjoy hands-on artistic experiences during their Chicago staycation adventure.
These cultural activities turn regular city stays into amazing adventures. They give you a fresh point of view on Chicago’s artistic heritage. You can join private museum tours, visit hidden galleries, or create art with local artists to connect with the city’s cultural soul.
Indulge in Culinary Adventures
Chicago’s food scene unfolds like a map that leads food lovers to memorable staycation spots. The city has countless ways to learn about its rich food heritage through intimate chef’s counters and busy market tours.
Chef’s Table Experiences
The city’s best dining spots are at chef’s counters where you can watch culinary artists at work. Girl & The Goat has four special chef’s counter seats where the culinary team serves unique tastings to guests. Food enthusiasts can book seats at Roister Restaurant up to three months ahead to watch Chef Andrew Brochu work his magic at the hearth.
Eden Chicago welcomes guests with eight counter seats that look right into the kitchen. They grow their own produce in a 500-square-foot greenhouse. Couples looking for a special Chicago staycation will love El Che Bar’s Mesa Cincuenta y Quatro. It serves an exclusive menu just for two.
Food Market Tours with Local Experts
Local professional chefs guide small groups through Chicago’s food scene and show hidden gems you won’t find alone. Chef Driven Food Tours lets guests enjoy unlimited portions and craft drinks while they learn about real neighborhoods away from downtown chains.
Secret Food Tours Chicago takes you to six local spots. You’ll taste great food while learning about culture and architecture. These tours make perfect one-day adventures, especially in areas like the West Loop where you can visit the famous Restaurant Row.
Cooking Classes with Chicago Chefs
A Chicago staycation becomes more fun when you join hands-on cooking sessions. Local cooking schools offer many choices:
- Italian cuisine classes where you make fresh pasta
- Cooking with spirits and wine
- Private cooking events for special occasions
Naveen’s Cuisine has taught cooking for 16 years. They focus on Indian and Thai cooking classes that work great for date nights or groups. Beginners build confidence while experienced cooks learn advanced techniques.
Families planning a Chicago staycation can choose from flexible booking options. Many places offer both in-person and virtual classes. These fun sessions teach cooking skills and help you learn about Chicago’s diverse food heritage. They fit perfectly into any Chicago staycation plan.
Experience Urban Nature Escapes
Chicago’s urban landscape hides a green wonderland of secret gardens and natural retreats. Nature lovers can find peace in the city’s 8,800 acres of parks and preserves. These spots make perfect getaway locations for a refreshing staycation.
Secret Garden Tours
The Lurie Garden sits as a peaceful sanctuary in Millennium Park, away from downtown’s buzz. Couples looking for quiet moments during their Chicago staycation will love this natural setting. The Alfred Caldwell Lily Pool lies just north, where visitors can find a hidden waterfall, council ring, and native plants.
Humboldt Park’s historic Formal Garden stands as evidence of landscape architect Jens Jensen’s 1908 design. This hidden gem is under restoration now but gives visitors a real taste of Chicago’s architectural history. It’s a must-see spot during any Chicago staycation.
Lakefront Wellness Activities
The Chicago Park District runs complete wellness programs along the beautiful 18-mile Lakefront Trail. Visitors can enjoy:
- Guided fitness classes and nutrition education programs
- Outdoor yoga sessions with skyline views
- Wellness-related special events throughout the year
- Access to 70+ fitness centers with modern equipment
The trail connects several beaches and parks. Guests at Chicago’s best staycation hotels can swim, paddleboard, and kayak here.
Hidden Park Discoveries
The North Park Village Nature Center sits quietly on the northwest side. Its 2.5 miles of hiking trails wind through wetlands, prairies, and oak savannas. Families on a Chicago staycation can explore nature here for free.
Jackson Park’s Garden of Phoenix brings a peaceful Japanese garden experience. The surrounding 500-acre park holds many hidden spots. Bird watchers love the park’s Wooded Island, which makes a perfect spot for day-long nature trips.
The Forest Preserve District of Cook County protects 70,000 acres of greenspace. This big network has 22 nature preserves and six nature centers. Visitors can find adventures here all year round.
These urban nature spots show why staying near these green spaces gives visitors the best of both worlds – city life and natural retreats. Each place lets people connect with nature while staying close to urban conveniences.
Uncover Local Entertainment Secrets
Chicago’s bustling streets hide a world of secret entertainment venues that create unforgettable staycation memories. These hidden gems range from prohibition-era jazz clubs to modern speakeasies and provide cozy settings for memorable nights out.
Underground Jazz Clubs
The Green Mill, Chicago’s oldest operating jazz club and a former Al Capone hangout, still stands proudly. This Uptown gem keeps its 1920s charm alive with nightly performances that run until 1:11 AM on weekdays and 2 AM on weekends. The Underground Wonder Bar ranks among America’s top 50 jazz clubs and delivers a rich mix of jazz, blues, rock, and reggae in a cozy setting.
Music lovers will find Guarneri Hall a true hidden treasure. This exclusive 60-seat venue in the Loop has attracted local and international artists since 2019. Each performance ends with a personal artist meet-and-greet that makes every show special.
Speakeasy Cocktail Experiences
The city’s speakeasy scene adds magic to any Chicago staycation. The eight-seat Milk Room needs advance booking and showcases vintage spirits. You’ll discover:
- A stained-glass entrance with prohibition-era charm
- Masterfully crafted, spirit-forward cocktails
- Hard-to-find whiskey collections
- A mysterious entrance with just a velvet rope marker
Sushi Suite 202 puts a fresh spin on the speakeasy concept with an exclusive sushi experience behind an unmarked hotel door. The Roar on Rush brings theater to life through a four-room cocktail journey set in prohibition times, complete with actors and storytelling.
Private Theater Performances
The city’s theater scene boasts intimate venues that make staycations memorable. Steppenwolf Theater’s 1700 Theater welcomes guests to an 80-seat space perfect for cabaret-style shows. Couples on a Chicago staycation will love this versatile venue’s mix of dance and live music.
Chicago Shakespeare Theater’s spaces include the cozy 180-seat Carl and Marilynn Thoma Upstairs Studio. Families enjoy special pre- and post-show activities that create lasting memories.
Broadway in Chicago’s Suite Service takes theater nights to new heights with private facilities that host up to 50 people. These exclusive spaces turn any best Chicago hotel staycation into something extraordinary.
Chicago shows that amazing adventures are waiting right outside your doorstep. The city’s handpicked experiences turn ordinary moments into unforgettable staycation stories, from historic boutique hotels to secret rooftop pools.
Couples can enjoy luxury retreats tucked away in architectural landmarks. The city’s cultural spots give you exclusive behind-the-scenes access. Food lovers can join chefs at hidden counters, while nature enthusiasts find peace along urban gardens and lakefront paths.
The best Chicago hotels blend naturally with these experiences and create perfect starting points to explore. The city’s neighborhoods give you countless ways to discover local gems, whether you want a full weekend getaway or just a day’s adventure.
These hidden spots show why Chicago staycations are just as good as traditional vacations. You’ll find world-class amenities, rich culture, and natural beauty just steps from home. The city’s special moments are ready to turn your everyday life into an unforgettable adventure.
Some FAQs about staycation Chicago experience:
What part of Chicago is best to stay in?
The best part of Chicago to stay in depends on your preferences, but downtown areas like The Loop and River North are ideal for a staycation Chicago experience. These neighborhoods are close to major attractions, restaurants, and the best staycation hotels Chicago has to offer.
Why is staycation a trend?
Staycations have become a trend due to their affordability and convenience. Many people prefer exploring local attractions, like those found in a Chicago staycation, rather than traveling long distances. They’re perfect for families or individuals seeking relaxation without the hassle of travel.
Is Chicago a good holiday destination?
Yes, Chicago is an excellent holiday destination with its world-class museums, diverse food scene, and iconic landmarks like Millennium Park. A staycation in Chicago offers the chance to explore the city like a tourist while enjoying local comforts.
Where do celebrities stay when visiting Chicago?
Celebrities visiting Chicago often stay in luxury hotels like The Peninsula or Waldorf Astoria, which are some of the best staycation hotels Chicago has to offer. These establishments offer privacy, comfort, and proximity to the city’s top attractions.
What is the safest area to stay around Chicago?
The safest areas to stay in Chicago include Lincoln Park, Gold Coast, and Streeterville. These neighborhoods are perfect for a staycation Chicago for families, with a mix of safety, entertainment, and amenities.
How many days to stay in Chicago?
Three to five days are typically enough to explore Chicago’s top attractions, enjoy its vibrant food scene, and experience a relaxing Chicago staycation. However, longer stays allow for deeper exploration of the city’s neighborhoods.
What is a good month to visit Chicago?
The best months to visit Chicago are May through September when the weather is warm, and outdoor events are plentiful. A summer staycation in Chicago is ideal for enjoying festivals, beaches, and rooftop dining.
What is the #1 tourist attraction in Chicago?
Millennium Park, featuring the iconic Cloud Gate sculpture (also known as “The Bean”), is the #1 tourist attraction in Chicago. It’s a must-visit spot for anyone planning a staycation Chicago experience.
Is Chicago very walkable?
Yes, Chicago is one of the most walkable cities in the United States. Staying downtown during your staycation in Chicago provides easy access to attractions, restaurants, and parks by foot.
Where does Beyonce stay in Chicago?
When in Chicago, Beyoncé is rumored to stay in luxury accommodations like The Peninsula or The Four Seasons, both known for their high-end services. These hotels are also excellent options for a glamorous Chicago staycation.
What is the touristy part of Chicago?
The Magnificent Mile and Navy Pier are the most touristy parts of Chicago. These areas are bustling with shops, restaurants, and activities, making them popular spots for a staycation Chicago for families.
What celebrities live in Trump Tower Chicago?
Trump Tower Chicago is home to several celebrities, including athletes, business moguls, and entertainers. Its central location and luxurious amenities make it a sought-after residence and an impressive sight during a Chicago staycation.
