A staycation in Chicago provides a unique opportunity to experience the city’s diverse attractions and activities without the hassle of travel. Whether you’re a local looking for a quick escape or a visitor wanting to explore more deeply, Chicago offers plenty of options to make your staycation memorable. From luxurious hotels and vibrant neighborhoods to world-class museums and scenic parks, here’s a comprehensive guide to planning the ultimate staycation in Chicago.
Stay in Style: Luxurious Hotels and Unique Accommodations
Start your staycation by choosing the perfect place to stay. Chicago boasts a variety of luxurious hotels and unique accommodations that cater to different tastes and preferences.
The Peninsula Chicago Located in the heart of the Magnificent Mile, The Peninsula Chicago is a five-star hotel known for its opulence and impeccable service. Enjoy a pampering spa treatment, dine at the award-winning Shanghai Terrace, and take a dip in the indoor pool with stunning city views.
The Robey For a more boutique experience, consider The Robey in Wicker Park. This trendy hotel combines Art Deco elegance with modern amenities. Relax at the rooftop lounge, Cabana Club, which offers panoramic views of the Chicago skyline, or explore the vibrant neighborhood filled with shops, bars, and restaurants.
Longman & Eagle If you prefer something more eclectic, Longman & Eagle in Logan Square is an excellent choice. This gastro-pub and inn features six uniquely decorated rooms above a Michelin-starred restaurant. Enjoy a rustic, cozy atmosphere with easy access to Logan Square’s hip nightlife.
Neighborhood Exploration: Discover Chicago’s Diverse Areas
Chicago’s neighborhoods each have their own distinct character and charm. Exploring these areas can make for a fascinating staycation experience.
Lincoln Park Home to the famous Lincoln Park Zoo, this neighborhood offers a mix of natural beauty and cultural attractions. Visit the Chicago History Museum, stroll through the lush Lincoln Park Conservatory, or enjoy a picnic by the lake.
Wicker Park/Bucktown Known for its hipster vibe, Wicker Park and Bucktown are filled with indie boutiques, record stores, and trendy cafes. Check out the art galleries along Milwaukee Avenue, grab a coffee at the iconic Wormhole Coffee, and enjoy live music at one of the many local venues.
Pilsen Pilsen is a vibrant, artsy neighborhood known for its colorful murals and rich Mexican heritage. Visit the National Museum of Mexican Art, explore the street art, and savor authentic Mexican cuisine at local eateries like Nuevo Leon.
Cultural Immersion: Museums and Theaters
Chicago’s cultural scene is one of the best in the country, offering a wealth of museums and theaters to explore.
Art Institute of Chicago One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an impressive collection of artworks from around the world. Don’t miss iconic pieces like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.”
Field Museum Dive into natural history at the Field Museum, home to Sue, the largest and most complete T. rex ever discovered. Explore exhibits on ancient civilizations, wildlife, and geology.
Chicago Theatre District For theater enthusiasts, the Chicago Theatre District offers a variety of shows, from Broadway hits to original productions. Catch a performance at the historic Chicago Theatre or the Goodman Theatre for an unforgettable night out.
Outdoor Adventures: Parks and Waterfront Activities
Take advantage of Chicago’s beautiful outdoor spaces for some fresh air and exercise.
Millennium Park Millennium Park is a must-visit, with its iconic Cloud Gate sculpture (affectionately known as “The Bean”), the interactive Crown Fountain, and the serene Lurie Garden. During the summer, enjoy free concerts and movies at the Jay Pritzker Pavilion.
Lakefront Trail Stretching 18 miles along Lake Michigan, the Lakefront Trail is perfect for biking, running, or a leisurely walk. Take in the scenic views of the lake and the city skyline, and stop at one of the many beaches along the way for a relaxing break.
Chicago Riverwalk The Chicago Riverwalk offers a picturesque setting for a stroll or a boat ride. Explore the architectural gems along the river, dine at one of the waterfront restaurants, or rent a kayak for a unique perspective of the city.
Culinary Delights: Chicago’s Food Scene
No staycation in Chicago is complete without indulging in the city’s renowned culinary offerings.
Deep-Dish Pizza Experience Chicago’s famous deep-dish pizza at legendary spots like Lou Malnati’s, Giordano’s, or Pequod’s. With its thick, buttery crust and layers of cheese and toppings, this hearty dish is a must-try.
Fine Dining For a more upscale dining experience, reserve a table at Alinea, a three-Michelin-star restaurant known for its innovative and artistic approach to cuisine. Alternatively, Oriole offers an intimate dining experience with a multi-course tasting menu that highlights seasonal ingredients.
Ethnic Eats Chicago’s diverse population is reflected in its rich culinary scene. Explore Chinatown for delicious dim sum, head to Devon Avenue for authentic Indian and Pakistani cuisine, or visit Greektown for classic Mediterranean dishes.
Unique Experiences: Off the Beaten Path
For those seeking something a bit different, Chicago offers plenty of unique experiences.
The 606 The 606 is an elevated trail that repurposes an old railway line, stretching through several neighborhoods including Wicker Park and Bucktown. Walk, bike, or jog along the trail and enjoy the public art installations and green spaces along the way.
Alfred Caldwell Lily Pool Escape to a hidden oasis in Lincoln Park with a visit to the Alfred Caldwell Lily Pool. This serene spot features native plants, winding paths, and a tranquil pond, offering a peaceful retreat from the hustle and bustle of the city.
Underground Donut Tour Indulge your sweet tooth with the Underground Donut Tour, a guided tour that takes you to some of the best donut shops in Chicago. Sample a variety of flavors and styles while learning about the city’s donut history.
Family-Friendly Activities: Fun for All Ages
If you’re planning a staycation with kids, Chicago has plenty of family-friendly attractions.
Navy Pier Navy Pier is a family favorite with its amusement rides, including the iconic Centennial Wheel, as well as shops, restaurants, and the Chicago Children’s Museum. During the summer, enjoy fireworks displays on Wednesday and Saturday nights.
Shedd Aquarium Explore the underwater world at Shedd Aquarium, home to thousands of marine animals including sharks, dolphins, and beluga whales. The interactive exhibits and live animal shows make it a hit with kids of all ages.
Adler Planetarium The Adler Planetarium offers a fascinating journey through space with its immersive exhibits and stunning sky shows. Kids can learn about the planets, stars, and the history of space exploration in a fun and engaging way.
Wellness Retreats: Relax and Rejuvenate
For those looking to unwind and recharge, Chicago offers several wellness retreats and spas.
AIRE Ancient Baths AIRE Ancient Baths in River West offers a luxurious and serene spa experience inspired by ancient Roman, Greek, and Ottoman traditions. Relax in thermal baths, enjoy a soothing massage, and unwind in the tranquil atmosphere.
Chuan Spa Located in The Langham hotel, Chuan Spa offers a holistic wellness experience with treatments based on traditional Chinese medicine. Indulge in a variety of massages, facials, and body treatments designed to rejuvenate your mind and body.
Allyu Spa Allyu Spa, situated on the Chicago River, provides a peaceful retreat with a focus on eco-friendly practices. Enjoy a range of treatments, including massages, facials, and energy work, in a serene and soothing environment.
Shopping Sprees: Retail Therapy
Chicago is a shopper’s paradise with its mix of high-end boutiques, department stores, and unique local shops.
Magnificent Mile The Magnificent Mile is Chicago’s premier shopping destination, featuring a mile of upscale stores, including flagship locations for brands like Apple, Nike, and Burberry. Explore the historic Water Tower Place and the chic shops along Oak Street.
Armitage Avenue For a more boutique shopping experience, head to Armitage Avenue in Lincoln Park. This charming street is lined with independent shops and trendy boutiques offering everything from fashion and home decor to unique gifts.
Andersonville Andersonville is known for its diverse array of locally-owned shops and vintage stores. Explore the neighborhood’s quirky boutiques, specialty food shops, and unique home goods stores for one-of-a-kind finds.
Nightlife and Entertainment: Evening Fun
When the sun goes down, Chicago’s vibrant nightlife and entertainment scene comes alive.
Live Music Chicago is famous for its live music venues. Catch a blues performance at Buddy Guy’s Legends, enjoy jazz at the Green Mill, or see a concert at the iconic Chicago Theatre.
Comedy Clubs For a night of laughter, visit one of Chicago’s renowned comedy clubs. The Second City is a legendary improv theater that has launched the careers of many famous comedians, while Zanies offers stand-up performances from top-notch talent.
Rooftop Bars Chicago’s skyline is best enjoyed from one of its many rooftop bars. Sip cocktails at Cindy’s Rooftop, the J. Parker, or LondonHouse Rooftop while taking in panoramic views of the city.
Conclusion
A staycation in Chicago offers endless possibilities for exploration, relaxation, and fun. Whether you’re a local looking to rediscover your city or a visitor wanting to delve deeper into its offerings, this guide provides a comprehensive overview of what makes Chicago an ideal staycation destination. From luxurious accommodations and vibrant neighborhoods to cultural landmarks and outdoor adventures, your perfect Chicago staycation awaits.
