Best Chicago Staycations
Find Your Chicago Getaway Today
Looking to experience Chicago in a new way? A Staycation in the Windy City offers countless opportunities to relax, explore, and discover hidden gems. From vibrant neighborhoods and iconic food spots to family-friendly attractions, wellness experiences, outdoor adventures, and even pet-friendly spots, Chicago is packed with ways to make your local getaway memorable.
We’ve crafted a guide to help you plan the perfect Staycation, along with a list of top hotels offering special packages, so you can unwind without traveling far.
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Your Chicago Staycation Guide
Explore Chicago’s Neighborhood Gems: Must-Visit Areas for a Staycation
Chicago’s neighborhoods each have their own distinct character, culture, and charm, making a Staycation in the Windy City feel like an adventure. From historic districts to trendy hotspots, these neighborhoods offer everything from great food and local shopping to art and outdoor fun. Here’s a guide to some must-visit areas that capture the essence of the city and make your experience unforgettable.
Wicker Park
Bohemian Vibes and Trendy Boutiques
Wicker Park is known for its eclectic mix of boutiques, cafés, and art galleries. Walk along Milwaukee Avenue and discover independent shops like Una Mae’s for unique clothing and Myopic Books for a massive selection of used books. Foodies will love dining at places like Big Star for tacos or The Violet Hour for craft cocktails in a hidden, speakeasy-style bar. If you’re looking to relax outdoors, head to Wicker Park itself for people-watching, a leisurely walk, or a quick game of basketball.
Lincoln Park
Family-Friendly Fun with a Touch of Nature
Perfect for a family-friendly Staycation, Lincoln Park offers a mix of urban amenities and natural beauty. Spend the day at the Lincoln Park Zoo, one of the country’s oldest zoos and free to the public, where you can see everything from lions to penguins. For a more tranquil experience, visit the Alfred Caldwell Lily Pool, a hidden gem with serene landscapes and a pond. Don’t miss a stop by Lincoln Park Conservatory to explore tropical plants and rare flowers, a perfect indoor escape on colder days.
West Loop
Foodie Paradise in a Historic Setting
The West Loop has become one of Chicago’s premier dining destinations, filled with celebrated restaurants and chic industrial spaces. Start with a bite at Au Cheval, known for one of the city’s best burgers, or try Girl & The Goat, one of Chef Stephanie Izard’s popular spots. If you’re a fan of Italian cuisine, visit Monteverde for handmade pasta. For a bit of shopping, head to Randolph Street Market (check for seasonal dates), a massive vintage and antique market filled with unique finds.
Hyde Park
Historical Sites and Cultural Institutions
Hyde Park is a must-visit for history buffs and culture lovers. Start your day at the Museum of Science and Industry, a massive museum with interactive exhibits on everything from space to submarines. Don’t miss a stroll around the University of Chicago campus, known for its stunning Gothic architecture. For a peaceful outdoor escape, head to the Jackson Park Japanese Garden, a beautifully designed garden where you can enjoy a quiet retreat from the bustling city.
Logan Square
Hipster Hangouts and Green Spaces
Logan Square is one of Chicago’s trendiest neighborhoods, filled with coffee shops, bars, and a laid-back atmosphere. Start your morning with a coffee from Intelligentsia or Gaslight Coffee Roasters before browsing local shops like Wolfbait & B-Girls, known for handmade and locally crafted goods. Take a walk along Logan Boulevard, where you’ll find a lovely tree-lined path and small parks. In the evening, stop by Revolution Brewing for a local craft beer and delicious pub food.
Old Town
Historic Charm and Entertainment
For a blend of history and nightlife, head to Old Town. Wander down the historic streets and explore landmarks like St. Michael’s Church, one of the few buildings that survived the Great Chicago Fire. Comedy fans should make a reservation at The Second City, the legendary comedy club where many famous comedians got their start. For a delicious dinner, try Topo Gigio for classic Italian fare or The Vig for a more modern menu with a lively atmosphere.
With its diverse neighborhoods, each offering unique experiences, booking a short getaway city allows you to explore the city in a new light. From bohemian Wicker Park to the historic streets of Old Town, there’s a neighborhood for every mood and interest, making your Staycation a true urban adventure.
Indulge in Chicago’s Culinary Scene: Iconic Eats and Hidden Finds
Chicago is renowned for its vibrant food scene, offering a mix of iconic dishes and hidden gems that cater to every taste. From famous deep-dish pizza to trendy cocktail bars, the city is a food lover’s paradise. Here’s a guide to some must-try culinary experiences that will delight your taste buds.
Deep-Dish Pizza
A Chicago Classic That Can’t Be Missed
No culinary tour of Chicago would be complete without trying the city’s iconic deep-dish pizza. Head to Lou Malnati’s or Giordano’s for a slice of this cheesy, sauce-laden masterpiece. If you’re looking for a twist on tradition, try Pequod’s Pizza, famous for its caramelized crust and loyal local following. Each spot offers its own unique spin on this Chicago favorite, making it a must-try for any Staycationer.
Street Food and Hot Dogs
Get a Taste of the City’s Best Casual Eats
Chicago is known for its unique take on the hot dog, topped with mustard, onions, relish, pickles, tomatoes, and a dash of celery salt – with no ketchup in sight! Visit Portillo’s for a classic Chicago-style dog, or head to Superdawg Drive-In for a nostalgic experience with curbside service. For a taste of more diverse street eats, explore the Maxwell Street Market on Sundays, where you’ll find everything from tamales to tacos and local delicacies like pork chop sandwiches.
Steakhouses and Fine Dining
Indulge in Chicago’s Iconic Steakhouse Culture
Chicago’s steakhouses are legendary, offering old-school vibes and expertly prepared cuts of meat. Visit Gibsons Bar & Steakhouse for a true Chicago experience, where you can enjoy a classic steak in a bustling atmosphere. For a modern twist on steak, try Bavette’s Bar & Boeuf, a stylish spot with a Prohibition-era feel. Another gem is Chicago Cut Steakhouse, known for its scenic views of the Chicago River and impeccable service.
Hidden Cocktail Bars and Speakeasies
Discover Secret Spots for Unique Drinks
Chicago has an array of hidden cocktail bars that make for a memorable night out. Start with The Violet Hour in Wicker Park, a speakeasy-style bar famous for its creative cocktails and intimate setting. For an unforgettable experience, head to Three Dots and a Dash, a tiki bar hidden in an alley behind the bustling River North area, where you’ll find tropical cocktails in a fun, immersive atmosphere. For a more laid-back vibe, check out Lazy Bird in the West Loop, known for its cozy setting and expertly crafted drinks.
Ethnic Neighborhood Eats
Explore Diverse Flavors Across the City
Chicago’s ethnic neighborhoods offer a world of culinary experiences. Visit Chinatown for authentic dim sum at Chiu Quon Bakery or fresh noodles at Qing Xiang Yuan Dumplings. For a taste of Mexican flavors, head to Pilsen and try the tacos at Taqueria El Milagro or a classic churro at La Catedral Cafe & Restaurant. In West Ridge, known as the city’s Little India, explore aromatic curries and freshly baked naan at Sabri Nihari.
Brunch Spots with Local Flair
Start Your Day with Chicago’s Best Brunches
Chicago is a brunch-lover’s haven, offering cozy spots and creative menus. Visit The Bongo Room in Wicker Park for indulgent pancake creations like the white chocolate and caramel pretzel pancake. For something unique, try Little Goat Diner in the West Loop, where the menu features inventive twists on comfort food classics. Another great option is Beatrix in River North, known for its vibrant ambiance, delicious pastries, and coffee bar.
With its culinary diversity, Chicago offers a Staycation full of flavor and discovery. From iconic dishes to hidden finds, the city’s food scene has something for every taste and style. Get ready to eat your way through Chicago!
Ultimate Family Fun in Chicago: Activities for Kids and Parents Alike
Chicago is an incredible city for family-friendly adventures, with activities that are engaging for both kids and parents. From museums with hands-on exhibits to outdoor spaces perfect for exploring, a Chicago Staycation with the family offers plenty of fun. Here’s a guide to some of the top family-friendly activities that will make your local getaway memorable.
Lincoln Park Zoo
A Day with the Animals for All Ages
The Lincoln Park Zoo is a must-visit for families and one of the oldest free zoos in the country. Kids and adults alike will enjoy seeing lions, gorillas, penguins, and more in beautifully designed habitats. During warmer months, take a ride on the Endangered Species Carousel or visit the petting zoo for a hands-on experience. Located in Lincoln Park, the zoo also offers scenic views of the Chicago skyline, making it a perfect spot for photos.
Museum of Science and Industry
Interactive Exhibits and Endless Curiosity
The Museum of Science and Industry in Hyde Park is a fantastic destination for families. Known for its massive, interactive exhibits, this museum lets kids explore everything from a real German U-boat to a full-size replica of a coal mine. Younger visitors will enjoy the Science Storms exhibit, where they can learn about natural phenomena like tornadoes and avalanches. With hands-on activities and awe-inspiring displays, this museum is a great way to spend an educational and entertaining day.
Navy Pier
Rides, Games, and Waterfront Views
Navy Pier is a family favorite for its variety of attractions, including carnival rides, games, and boat cruises on Lake Michigan. Take a ride on the iconic Centennial Wheel for amazing views of the city skyline. Kids will love exploring the Chicago Children’s Museum located on the pier, featuring interactive exhibits and play areas. For some fun in the water, check out the sightseeing cruises or a relaxing water taxi ride. Navy Pier is a one-stop destination for family-friendly entertainment.
Millennium Park
Iconic Art and Outdoor Play
Millennium Park offers a mix of open spaces, public art, and play areas, making it an ideal spot for families. Kids will love the Cloud Gate (better known as “The Bean”), where they can see their reflection in the shiny, mirrored surface. During the summer, the Crown Fountain is a hit, with interactive water jets that are perfect for cooling off on warm days. For a peaceful break, head to the Lurie Garden and explore its paths and seasonal flowers.
Adler Planetarium
Explore the Wonders of Space
The Adler Planetarium is a fantastic place for budding astronomers and curious minds. Kids can learn about the solar system, touch a piece of the moon, and experience immersive shows in the dome theater. The Planet Explorers exhibit is designed just for children, allowing them to role-play as astronauts and scientists. Located on the lakefront, the planetarium also offers stunning views of the Chicago skyline, making it a fun and educational outing.
Maggie Daley Park
Playgrounds, Skating, and Adventure
Maggie Daley Park is a dream playground for kids, featuring everything from a climbing wall to the imaginative Play Garden, designed with multiple play areas for children of all ages. In the winter, the ice-skating ribbon offers a scenic outdoor skating experience, and in the summer, kids can climb, slide, and explore to their hearts’ content. The park’s lush landscapes and proximity to Lake Michigan make it a beautiful setting for family adventures.
With so many family-friendly activities, Chicago is a fantastic place for a Staycation that’s fun for all ages. From the excitement of Navy Pier to the hands-on exhibits at the Museum of Science and Industry, your family will find endless ways to explore and enjoy this amazing city.
Chicago Wellness Experiences: Spa Days, Yoga Retreats, and Outdoor Wellness
Chicago offers a variety of wellness experiences perfect for a relaxing Staycation. From serene spa treatments to lakeside yoga and lush green spaces, there are countless ways to unwind and rejuvenate in the city. Here’s a guide to some of the best wellness activities to make your stay both refreshing and restorative.
Luxury Spa Days
Pamper Yourself with High-End Treatments
For the ultimate in relaxation, treat yourself to a day at one of Chicago’s top luxury spas. The Peninsula Spa Chicago is renowned for its tranquil atmosphere and extensive range of treatments, from facials to therapeutic massages. Another top choice is the Waldorf Astoria Spa in the Gold Coast, where you can enjoy custom treatments in a beautifully designed setting. For a unique experience, try the Allyu Spa in River North, which offers holistic treatments inspired by nature, including infrared saunas and river stone massages.
Yoga and Meditation Studios
Find Inner Peace in Chicago’s Best Studios
Chicago has numerous yoga studios offering classes and retreats perfect for a wellness-focused Staycation. Yoga Six offers a variety of classes, from Vinyasa to hot yoga, ideal for stretching and strengthening. For meditation, visit Chill Meditation + Massage in River North, where you can drop in for guided meditation or try a meditation and massage combo. Another favorite is Exhale in the Gold Coast, where you can join classes in barre, cardio, and yoga, all designed to rejuvenate the mind and body.
Lakeside Wellness Activities
Embrace Outdoor Wellness by Lake Michigan
Enjoy the fresh air and beautiful scenery with wellness activities along Lake Michigan. Start your day with a morning yoga class at Oak Street Beach, where you can enjoy the lakefront views while practicing your sun salutations. For a unique experience, try paddleboard yoga with Chicago SUP, which offers classes directly on the water. The Lakefront Trail is also perfect for a peaceful walk or bike ride, stretching for miles along the shoreline with scenic city views.
Botanic Gardens and Green Spaces
Reconnect with Nature in Tranquil Outdoor Settings
For a wellness experience immersed in nature, visit the Chicago Botanic Garden in Glencoe. This expansive garden features themed landscapes, serene walking paths, and peaceful water views, making it an ideal spot for relaxation and reflection. Another beautiful option is the Alfred Caldwell Lily Pool in Lincoln Park, a hidden gem with lush greenery, a small waterfall, and a calming atmosphere. These green spaces allow you to escape the city hustle and unwind in natural beauty.
Float Therapy and Infrared Saunas
Detoxify and Decompress in Innovative Wellness Spaces
If you’re looking to try something unique, float therapy and infrared saunas are excellent options. Visit Float Sixty in River North for float therapy, where you can relax in a sensory deprivation tank that helps reduce stress and improve mindfulness. For an infrared sauna session, check out Lume Wellness in the West Loop, which offers a modern take on traditional sauna therapy to help detoxify and revitalize your body. Both experiences are ideal for unwinding and refreshing your mind and body.
Healthy Dining and Juice Bars
Nourish Your Body with Organic and Plant-Based Eats
Part of any wellness Staycation is eating well, and Chicago has many spots focused on health-conscious meals. Stop by Left Coast Food & Juice in River North for nourishing salads, grain bowls, and cold-pressed juices. For a plant-based meal, try Chicago Diner in Lakeview, a local favorite known for its vegan comfort food. Another great option is Harvest Juicery in the West Loop, where you can enjoy fresh smoothies, juices, and superfood bowls that are as delicious as they are nutritious.
Whether you’re looking to relax at a spa, practice yoga by the lake, or enjoy a healthy meal, Chicago offers a variety of wellness experiences to make your Staycation revitalizing. Take the time to recharge and enjoy the peaceful side of the Windy City.
Outdoor Adventures in Chicago: Parks, Trails, and Lake Activities
Chicago’s vibrant outdoor spaces and scenic lakefront make it an ideal city for those seeking fresh air and adventure. Whether you’re looking to hike, bike, or spend a relaxing day by the water, there’s something for every nature lover. Here’s a guide to some of the best outdoor activities to enjoy on your Chicago Staycation.
Explore the Lakefront Trail
A Scenic Path Along Lake Michigan
The Lakefront Trail is one of Chicago’s most beloved outdoor spaces, stretching for 18 miles along the shores of Lake Michigan. Whether you’re biking, jogging, or walking, this trail offers stunning views of both the city skyline and the lake. The trail is lined with beaches, parks, and picnic spots, making it perfect for an all-day adventure. Start at Montrose Beach for a quieter experience, or head south toward Oak Street Beach for a livelier atmosphere closer to downtown.
Lincoln Park
Nature Trails, Gardens, and Wildlife
Lincoln Park is a sprawling green space filled with things to do and see, from scenic trails to lovely gardens. Stroll through the Lincoln Park Conservatory, where you’ll find exotic plants and flowers year-round, or explore the North Pond Nature Sanctuary, a peaceful spot perfect for birdwatching and photography. Don’t forget to visit the Alfred Caldwell Lily Pool, a hidden gem with tranquil water features and lush landscapes. Lincoln Park offers a nature escape right in the heart of the city.
Chicago Riverwalk
Riverside Views and Waterfront Activities
The Chicago Riverwalk is a lively outdoor space where you can enjoy riverside views, outdoor dining, and a variety of activities. Rent a kayak from Urban Kayaks and paddle along the Chicago River for a unique perspective of the city. For a relaxing stroll, walk the length of the Riverwalk, stopping at spots like the Vietnam Veterans Memorial Plaza and the Floating Gardens. The Riverwalk also has plenty of restaurants and cafés, making it easy to grab a drink or a bite while taking in the sights.
Chicago Botanic Garden
Immerse Yourself in Lush Landscapes
Located just outside the city in Glencoe, the Chicago Botanic Garden is an expansive oasis of themed gardens, beautiful water features, and serene walking paths. Stroll through the Japanese Garden, Rose Garden, or the Fruit & Vegetable Garden for a peaceful experience surrounded by nature. The garden also offers seasonal events and plant sales, so check their calendar to see what’s happening during your visit. It’s a perfect spot for those looking to escape the urban hustle and immerse themselves in greenery.
Burnham Park and Promontory Point
Scenic Walks and Picnic Spots by the Lake
Burnham Park stretches along the lakefront from Grant Park to Jackson Park and offers plenty of quiet spots to relax by the water. For a unique experience, head to Promontory Point, a beautiful peninsula that extends into Lake Michigan, providing panoramic views of the city skyline. This area is perfect for a picnic, sunset views, or just relaxing by the lake. Burnham Park’s winding paths and open spaces make it an ideal destination for a low-key outdoor adventure.
Paddleboarding and Kayaking on Lake Michigan
Water Adventures with Stunning City Views
For a refreshing outdoor activity, try paddleboarding or kayaking on Lake Michigan. Chicago SUP at North Avenue Beach offers paddleboard rentals and classes, making it easy for beginners to try this water sport while enjoying views of the skyline. For kayaking, Kayak Chicago offers guided tours and rentals that let you explore the lake or paddle along the Chicago River. These water activities provide a unique perspective of the city and are perfect for adding a bit of adventure to your Staycation.
With its diverse parks, trails, and water activities, Chicago is full of outdoor adventures waiting to be discovered. From scenic trails along Lake Michigan to beautiful gardens and riverside paths, there are countless ways to enjoy nature in the city. Take advantage of these outdoor experiences to make your Staycation refreshing and memorable.
Bring Your Pup! Pet-Friendly Chicago Staycation Ideas
Chicago is a pet-friendly city with plenty of options for enjoying a Staycation with your furry friend. From dog parks and outdoor patios to scenic lakefront trails, there are many ways to explore the city with your pup by your side. Here’s a guide to the best pet-friendly activities for a memorable Staycation with your dog in Chicago.
Dog-Friendly Beaches
Sun, Sand, and Splashing Fun
One of the best ways to enjoy Chicago’s lakefront with your dog is at the city’s dog-friendly beaches. Montrose Dog Beach is a popular spot where your pup can run off-leash and splash in the water. It’s a spacious beach with plenty of room for dogs to play, swim, and socialize. For a quieter option, head to Belmont Harbor Dog Beach, where your dog can also enjoy some leash-free fun by the water. Remember to bring fresh water and a towel for a post-beach cleanup!
Dog Parks Around the City
Let Your Pup Run Free and Make Friends
Chicago has several well-maintained dog parks perfect for letting your pup off-leash. Wiggly Field Dog Park in Lincoln Park is a fenced area with plenty of space for dogs to run and play. For a more scenic option, try Grant Park’s Dog Friendly Area, located near the Museum Campus. Here, you’ll find a large fenced area and beautiful views of the city. Another popular spot is Puptown Dog Park in Uptown, which has agility equipment and shaded benches for dog owners.
Pet-Friendly Patios and Cafés
Enjoy a Meal or Coffee with Your Furry Friend
Many Chicago restaurants and cafés welcome pets on their patios, making it easy to dine with your dog. Visit Parson’s Chicken & Fish in Logan Square, where dogs are welcome on the outdoor patio, and you can enjoy fried chicken and cocktails. For a coffee break, check out Espresso & Milk in Lakeview, a cozy spot with a dog-friendly patio. Another great option is Wishbone in West Loop, where you and your pup can enjoy Southern comfort food on the outdoor patio.
Lakefront Walks and Trails
Scenic Paths Perfect for Strolling with Your Dog
The Lakefront Trail is a fantastic way to explore Chicago with your dog while enjoying beautiful views of Lake Michigan. This 18-mile trail stretches along the lake and is dotted with parks, grassy areas, and benches where you and your pup can rest. For a shorter walk, head to North Avenue Beach, where dogs are allowed on leashes and can enjoy the sights and sounds of the lakefront. These trails offer a perfect mix of exercise and relaxation.
Pet Boutiques and Treat Shops
Spoil Your Pup with Unique Finds
No Staycation is complete without a little shopping, and Chicago has several pet boutiques for treats, toys, and accessories. Tails in the City in the Gold Coast offers upscale pet products, from chic leashes to gourmet treats. Another favorite is Urban Pooch in Ravenswood, which has a great selection of toys, treats, and even dog-friendly ice cream. For holistic pet products, visit Wigglyville in Lakeview, where you can find organic treats and eco-friendly toys for your dog.
Dog-Friendly Events and Experiences
Enjoy Pet-Centric Activities and Socializing
Chicago hosts several dog-friendly events throughout the year, giving you a chance to enjoy unique activities with your pet. Check out ChiTown Drive In, which hosts outdoor movies where dogs are welcome, perfect for a cozy evening under the stars. For a more interactive experience, try Montrose Dog Beach Clean-Up Days, where you and your pup can help keep the beach clean and meet other dog owners. Many breweries, like Lagunitas Brewing Company in Pilsen, also host dog-friendly events on their patios, creating fun social opportunities.
With its variety of dog-friendly spaces, Chicago is the perfect city for a pet-inclusive Staycation. From beaches and parks to patios and boutiques, there are endless ways to make your Staycation fun and memorable for both you and your furry friend.
A Chicago Staycation offers the best of the city, allowing you to immerse yourself in everything the city has to offer – all while staying close to home. Whether you’re savoring deep-dish pizza, unwinding at a luxurious spa, exploring vibrant neighborhoods, or enjoying lakeside walks with your pup, each day is filled with unique experiences.
With family-friendly attractions like Navy Pier, wellness escapes along the lakefront, and an array of pet-friendly options, Chicago caters to every style. Plus, with hotel packages designed for you, you can enjoy all the perks of a vacation right here in your city. Embrace the city’s rich culture, vibrant dining, and endless outdoor adventures, and discover how a Staycation can be just as fulfilling as a trip away.