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How To Have A Staycation In Chicago


Modified: December 28, 2023

by Kiley Ricks



When it comes to taking a break from the routine and immersing oneself in a relaxing getaway, a staycation in Chicago is an excellent choice. Known as the “Windy City,” Chicago offers a diverse range of attractions and experiences that make it an ideal destination for a memorable staycation.


Whether you’re a local resident looking to explore your own city or a visitor seeking a unique urban getaway, Chicago has something for everyone. From world-class museums and iconic landmarks to vibrant neighborhoods and renowned culinary delights, this city offers a plethora of opportunities to create lasting memories.


Choosing to have a staycation in Chicago means you get to enjoy the comforts of home while immersing yourself in the excitement and beauty of the city. It’s a chance to take a break from the daily grind and embrace the culture, attractions, and hidden gems that make Chicago such a captivating destination.


In this guide, we’ll explore the various aspects of having a staycation in Chicago, including choosing the perfect spot, exploring local attractions, indulging in delicious cuisine, enjoying outdoor activities, relaxing at spas and wellness centers, uncovering hidden gems in different neighborhoods, immersing yourself in cultural experiences, and making the most of the city’s vibrant nightlife and entertainment scene.


Moreover, we’ll also provide tips on planning a budget-friendly staycation in Chicago, ensuring that you can have an unforgettable experience without breaking the bank.


So, let’s embark on a journey through the enchanting city of Chicago and discover how to have the perfect staycation filled with fun, relaxation, and exploration.


Choosing the Perfect Staycation Spot in Chicago

With so many vibrant neighborhoods and diverse accommodations to choose from, selecting the perfect staycation spot in Chicago can be an exciting task. Each neighborhood in the city has its own distinct character, offering unique experiences and attractions.


One popular option for a staycation is the downtown area, where you can find luxurious hotels with stunning views of the city’s iconic skyline. Staying downtown allows you to be within walking distance of renowned landmarks like Millennium Park, the Art Institute of Chicago, and Navy Pier. You’ll also have easy access to world-class shopping on the Magnificent Mile and an array of dining options to satisfy your culinary cravings.


If you prefer a more relaxed and residential vibe, consider staying in neighborhoods like Lincoln Park or Lakeview. These areas are known for their charming tree-lined streets, serene parks, and a variety of boutique shops and cozy restaurants. You can also explore attractions such as the Lincoln Park Zoo or catch a show at the historic Music Box Theatre.


For those seeking a vibrant and eclectic atmosphere, Wicker Park and Logan Square are excellent choices. These neighborhoods are brimming with trendy shops, hip bars, and unique eateries. You’ll find an abundance of street art, live music venues, and bustling farmers’ markets where you can immerse yourself in the local culture.


If you’re looking to experience a thriving arts and theater scene, consider staying in the Loop or the Near North Side. These areas are home to renowned theaters like the Chicago Theatre and the Goodman Theatre, where you can catch incredible performances. You can also explore the Museum of Contemporary Art or visit the Chicago Cultural Center to admire exquisite art exhibits.


When choosing your staycation spot, it’s important to consider your interests, preferences, and the type of experience you want to have. Whether you’re a foodie, an art enthusiast, or someone who enjoys outdoor activities, Chicago has a neighborhood that caters to your desires.


Once you’ve decided on the perfect staycation spot, it’s time to start planning your itinerary and exploring all the incredible attractions and experiences that Chicago has to offer.


Exploring Local Attractions and Landmarks

One of the highlights of a staycation in Chicago is the opportunity to explore the city’s famous attractions and landmarks. From architectural marvels to world-class museums, there’s no shortage of captivating destinations to visit.


A must-see landmark in Chicago is the iconic Willis Tower, formerly known as the Sears Tower. Visit the Skydeck on the 103rd floor for breathtaking views of the city skyline, and if you’re feeling adventurous, step out onto The Ledge, a glass balcony that extends from the building.


Another architectural gem is the Cloud Gate, affectionately known as “The Bean,” located in Millennium Park. This reflective sculpture designed by artist Anish Kapoor is a popular spot for tourists and locals alike. Capture unique photos and take in the mesmerizing reflections of the surrounding cityscape.


No visit to Chicago is complete without exploring its world-class museums. The Art Institute of Chicago houses an extensive collection of art, spanning centuries and continents. Admire famous paintings, sculptures, and artifacts, including Grant Wood’s “American Gothic” and Vincent van Gogh’s “The Bedroom.”


For science enthusiasts, the Museum of Science and Industry is a must-visit. Explore interactive exhibits, experience a simulated tornado, and stroll through a U-505 German submarine. It’s a fascinating opportunity to learn and engage in hands-on experiments.


Chicago is also known for its rich history, and a visit to the Chicago History Museum allows you to delve deeper into the city’s past. Learn about significant events, such as the Great Chicago Fire, and discover the stories of influential figures who shaped the city.


In addition to these renowned attractions, be sure to explore Chicago’s beautiful parks and waterfront areas. Take a leisurely stroll along the Lakefront Trail, enjoy a picnic in Grant Park, or rent a bike and cycle through the scenic paths of Lincoln Park.


Keep an eye out for special events and festivals happening throughout the year. From the Air and Water Show to the Taste of Chicago, there’s always something exciting happening in the city.


As you venture out to explore the local attractions and landmarks, be sure to check for any COVID-19 safety guidelines and restrictions in place. Some attractions may have modified hours or require advance reservations to ensure the safety of visitors.


Immerse yourself in the history, art, and culture that Chicago has to offer, and create unforgettable memories during your staycation.


Trying Out Delicious Chicago Cuisine

One of the highlights of any staycation in Chicago is indulging in the city’s renowned culinary scene. Known for its diverse and delicious food options, Chicago offers a wide range of dining experiences that are sure to satisfy any craving.


When it comes to iconic Chicago cuisine, deep-dish pizza is a must-try. Head to world-famous pizzerias like Lou Malnati’s, Giordano’s, or Pequod’s, where you can savor a thick, cheesy, and decadent slice of deep-dish pizza. The combination of a buttery crust, gooey cheese, and flavorful tomato sauce is an absolute delight for pizza enthusiasts.


Another Chicago classic is the Italian beef sandwich. Sink your teeth into a juicy and tender beef sandwich served on a crusty roll and topped with sweet or hot peppers. Portillo’s, Al’s Beef, and Mr. Beef are popular spots to sample this mouthwatering delicacy.


No visit to Chicago is complete without trying a Chicago-style hot dog. Enjoy a Vienna Beef hot dog nestled in a poppy seed bun and topped with mustard, relish, chopped onions, tomato slices, a pickle spear, and a sprinkle of celery salt. Don’t forget to skip the ketchup, as locals will remind you that it’s not part of the authentic experience.


If you’re a fan of street food, head to the food trucks scattered throughout the city. These mobile kitchens offer a variety of delectable options, from gourmet tacos and sliders to indulgent desserts like gourmet cupcakes and artisanal ice cream.


Chicago is also known for its vibrant food markets. Make your way to the bustling Chicago French Market or Revival Food Hall to sample an array of culinary delights from different vendors. From sushi and tacos to artisanal cheeses and pastries, these markets offer a feast for the senses.


For those with a sweet tooth, Chicago has plenty to offer. Don’t miss out on trying Garrett Popcorn, a beloved local institution known for its addictive blend of caramel and cheese popcorn. You can also satisfy your dessert cravings with a slice of Eli’s Cheesecake or a classic buttery pastry from Stan’s Donuts.


As you navigate the culinary landscape of Chicago, keep in mind that many restaurants are currently offering takeout and delivery options due to COVID-19 restrictions. Support local businesses by ordering from your favorite eateries or exploring new dining options.


From hearty comfort foods to gourmet delights, Chicago’s cuisine reflects the city’s vibrant and diverse culture. Explore the local culinary scene, venture outside your culinary comfort zone, and savor the flavors that make Chicago a food lover’s paradise.


Enjoying Outdoor Activities and Parks

During your staycation in Chicago, make the most of the city’s beautiful outdoor spaces and engage in a variety of activities that will allow you to enjoy the natural beauty of the surroundings.


One of the most popular outdoor destinations in Chicago is Millennium Park. Take a leisurely walk through the park and admire the iconic Cloud Gate sculpture, also known as “The Bean.” The park hosts many outdoor concerts, art installations, and festivals throughout the year, offering a vibrant atmosphere for visitors to enjoy.


Another must-visit park is Grant Park, also known as “Chicago’s Front Yard.” This expansive green space is home to the famous Buckingham Fountain, which features stunning water displays. Explore the park’s gardens, take a bike ride along the trails, or simply relax on the grass and soak in the sun.


If you’re looking for a more serene and picturesque setting, head to Lincoln Park. This 1,200-acre park offers lush green spaces, walking paths, and a beautiful zoo. Visit the Lincoln Park Conservatory to admire the stunning botanical displays and escape into a world of colorful flowers and tropical plants.


For outdoor enthusiasts, the Lakefront Trail is a perfect destination for biking, jogging, or simply enjoying a scenic walk along the shores of Lake Michigan. With breathtaking views of the lake and the city skyline, this trail provides a rejuvenating getaway from the hustle and bustle of the city.


If you’re interested in water activities, consider renting a kayak or paddleboard and exploring the Chicago River. Take in the architectural wonders as you paddle through the city’s waterways, or join a guided boat tour to learn about the history and architecture of the area.


For golf enthusiasts, there are several golf courses in and around the city where you can practice your swing. From public courses to private clubs, Chicago offers options for players of all skill levels.


During the winter months, don’t miss the opportunity to go ice skating at one of the city’s outdoor rinks. Millennium Park and Maggie Daley Park both offer skate rentals and a charming atmosphere to glide on the ice surrounded by the city lights.


As with any outdoor activity, it’s important to be mindful of safety and adhere to any park rules and guidelines. Pay attention to the weather conditions, stay hydrated, and wear appropriate gear for the activity you choose.


Whether you’re seeking a peaceful retreat in nature or an adrenaline-filled adventure, Chicago’s outdoor spaces and parks offer a multitude of opportunities for you to connect with the outdoors and enjoy the beauty of the city.


Relaxing and Unwinding at Chicago’s Spas and Wellness Centers

As you embark on your staycation in Chicago, take some time to rejuvenate your mind and body by indulging in the city’s top-notch spas and wellness centers. Escape the hustle and bustle of everyday life and immerse yourself in a world of tranquility and self-care.


Chicago is home to a wide range of spas that offer a variety of treatments designed to pamper and relax. From luxurious hotel spas to boutique wellness centers, you’ll find options to suit your preferences and needs.


Start your spa experience with a soothing massage. Choose from Swedish, deep tissue, hot stone, or aromatherapy massages to help release tension and promote deep relaxation. Many spas also offer customized massages tailored to your specific needs.


For those looking to rejuvenate their skin, facials are a popular choice. Treat yourself to a revitalizing facial that will cleanse, exfoliate, and nourish your skin, leaving you with a radiant and refreshed complexion. With an array of facial treatments available, you can find one that addresses your unique skincare concerns.


Many spas in Chicago also offer unique wellness experiences such as hydrotherapy sessions, body wraps, and detox treatments. Unwind in a tranquil environment and let your cares melt away as you enjoy these rejuvenating rituals.


In addition to traditional spa treatments, Chicago is also home to wellness centers that offer holistic practices to restore balance and promote overall well-being. Consider trying yoga or meditation classes to enhance your mindfulness and inner peace.


Some wellness centers in the city specialize in alternative therapies like acupuncture, reiki, or reflexology. These practices aim to restore energy balance and promote healing throughout the body.


Before booking your spa appointment, it’s advisable to check the availability and any special COVID-19 protocols in place to ensure your safety. Many spas have implemented extra precautions to prioritize the health and well-being of their guests.


After a day of pampering and self-care, take some time to relax in the peaceful ambiance of your accommodation. Savor a cup of herbal tea, read a book, or simply unwind and let the tranquility wash over you.


By treating yourself to a spa experience or indulging in wellness activities, you’ll leave your staycation in Chicago feeling rejuvenated, refreshed, and ready to take on the world.


Uncovering the Hidden Gems of Chicago’s Neighborhoods

While exploring the popular attractions of Chicago is a must during your staycation, don’t forget to venture off the beaten path and discover the hidden gems nestled within the city’s vibrant neighborhoods. Chicago is a city of neighborhoods, each with its own unique character and treasures waiting to be uncovered.


One neighborhood worth exploring is Pilsen, known for its vibrant art scene and Mexican influence. Take a stroll along 18th Street and admire the colorful murals that adorn the buildings. Visit the National Museum of Mexican Art to learn about the rich heritage and culture of the Mexican community in Chicago.


If you’re a music lover, make your way to Logan Square, where you’ll find a thriving indie music scene. Attend a live performance at local venues like the Logan Square Auditorium or Cole’s Bar, and discover talented up-and-coming musicians.


For a taste of Chicago’s jazz history, head to the Hyde Park neighborhood, home to the famous Hyde Park Jazz Festival. Enjoy live jazz performances at various venues throughout the neighborhood and soak in the soulful sounds that have defined the city’s music culture.


Andersonville is a charming neighborhood known for its unique shops and local boutiques. Explore the streets lined with independent stores, antique shops, and specialty stores offering everything from vintage clothing to handmade crafts.


Chicago is also home to many picturesque parks and gardens that offer a tranquil escape from the bustling city life. Visit the Osaka Garden in Jackson Park, a hidden gem inspired by traditional Japanese gardens. Enjoy a peaceful walk amidst the serene landscape, featuring a pond, bridges, and beautiful flora.


Another hidden gem is the Alfred Caldwell Lily Pool located within Lincoln Park. This serene oasis features a stunning lily pond, waterfalls, and lush greenery. Take a moment to relax and admire the beauty of this hidden gem.


For architecture enthusiasts, the Beverly neighborhood offers a delightful surprise. Take a stroll along the residential streets and marvel at the exquisite examples of Prairie School architecture, including several homes designed by renowned architect Frank Lloyd Wright.


These are just a few examples of Chicago’s hidden gems that await discovery in its diverse neighborhoods. Take the time to explore beyond the popular tourist spots and immerse yourself in the authentic and lesser-known aspects of the city. You never know what delightful surprises you’ll encounter along the way.


Taking Part in Cultural and Artistic Experiences

Chicago is a city bursting with cultural and artistic experiences that offer a glimpse into its rich history and vibrant creative scene. During your staycation, immerse yourself in the cultural fabric of the city and take part in the diverse range of artistic offerings.


Start by visiting the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore its vast collection, which spans centuries and continents, and marvel at masterpieces like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.”


For a taste of Chicago’s theater scene, catch a show at one of the renowned theaters in the Loop. The Chicago Theatre, the Goodman Theatre, and the Steppenwolf Theatre Company are just a few of the venues that showcase world-class performances, from classic plays to cutting-edge productions.


Take a stroll through the vibrant neighborhoods of Wicker Park and Ukrainian Village, known for their thriving arts scenes. Explore the numerous galleries that display works by local and international artists. You may even have the opportunity to meet the artists themselves and gain insight into their creative processes.


Chicago is also home to a rich music tradition. From blues and jazz to hip-hop and indie rock, the city has played a significant role in shaping the music landscape. Catch live performances at iconic music venues like the Chicago Symphony Orchestra at Symphony Center, the Chicago Jazz Showcase, or the iconic Green Mill Cocktail Lounge, where jazz legends once graced the stage.


The city hosts numerous cultural festivals throughout the year, providing a chance to celebrate and experience the diversity of different communities. From the Taste of Chicago, a food festival that showcases the city’s culinary delights, to the Chicago Cultural Festival, where you can explore the arts and traditions of various cultures, there’s always something happening to celebrate the city’s cultural tapestry.


For literature enthusiasts, Chicago has a rich literary history and a vibrant writing community. Attend a book reading or poetry slam at local bookstores and literary venues such as the Poetry Foundation or Women & Children First. You may even discover a hidden gem among the city’s independent publishers and bookshops.


Lastly, don’t forget to explore public art installations scattered throughout the city. From the iconic “Chicago Picasso” sculpture in Daley Plaza to the vibrant murals in the Pilsen neighborhood, these works of art bring beauty and creativity to unexpected places.


Chicago’s cultural and artistic experiences offer a window into the city’s soul. Immerse yourself in its vibrant arts scene, attend performances, explore galleries, and engage with the diverse range of artistic expressions. By doing so, you’ll gain a deeper appreciation for the city’s rich cultural heritage and contribute to the celebration of its thriving artistic community.


Making the Most of Chicago’s Nightlife and Entertainment Scene

When the sun sets, Chicago truly comes alive with its vibrant nightlife and entertainment scene. During your staycation, immerse yourself in the city’s energetic atmosphere and experience the diverse range of venues and activities that cater to every taste and preference.


Start your evening by exploring Chicago’s thriving bar scene. From trendy cocktail lounges to laid-back dive bars, the city offers a variety of options for socializing and enjoying creative libations. Head to places like The Violet Hour in Wicker Park or The Aviary in the West Loop, where talented mixologists craft unique and innovative cocktails that will tantalize your taste buds.


For music lovers, Chicago’s live music venues are a must-explore. From intimate jazz clubs to larger concert halls, the city’s diverse music scene caters to every genre. Catch a live performance at the historic Chicago Theatre, enjoy blues and jazz at Kingston Mines, or dance the night away to the beats of renowned DJs at popular nightclubs like Smartbar or Sound-Bar.


If you’re in the mood for a laughter-filled night, visit one of Chicago’s iconic comedy clubs. The city has a rich tradition of producing talented comedians, and you can catch performances at legendary venues like Second City or Zanies Comedy Club, where you might witness the next big comedic star in the making.


For a more interactive entertainment experience, consider visiting one of Chicago’s many entertainment complexes. Play a game of mini-golf at the innovative mini-golf bar, Punch Bowl Social, or challenge your friends to a game of bowling at a trendy bowling alley like Lucky Strike or 10pin Bowling Lounge.


If you’re looking for a unique and immersive entertainment experience, Chicago offers a range of interactive and themed experiences. Immerse yourself in a mysterious escape room adventure, participate in an interactive theater performance, or solve a thrilling mystery at a murder mystery dinner party.


Don’t forget to check out the city’s calendar for special events and performances happening during your staycation. From concerts and comedy shows to art exhibitions and film screenings, there’s always something exciting taking place in the city’s entertainment scene.


As you venture out into the nightlife and entertainment scene, make sure to plan your transportation accordingly to ensure a safe and enjoyable evening. Chicago offers a robust public transportation system, as well as rideshare services and taxis.


Whether you’re dancing the night away, enjoying live music, or immersing yourself in unique entertainment experiences, Chicago’s nightlife and entertainment scene will leave you with unforgettable memories and a taste of the city’s vibrant energy.


Planning a Budget-Friendly Staycation in Chicago

While Chicago offers a plethora of exciting experiences, it is possible to have a memorable staycation without breaking the bank. With a little planning and creativity, you can enjoy all that the city has to offer while staying within your budget.


Firstly, research and take advantage of free or low-cost activities. Many of Chicago’s top attractions offer free admission on certain days or discounted tickets during specific times. Check the websites or call ahead to find out about any special promotions or offers.


Exploring the city’s parks and public spaces is a great way to enjoy the outdoors without spending a dime. Take a picnic to Millennium Park, walk along the Lakefront Trail, or visit the Lincoln Park Zoo, which offers free admission.


Consider using public transportation to get around the city. The Chicago Transit Authority (CTA) offers affordable options such as the ‘L’ trains and buses, which can take you to various destinations throughout the city. Purchase a reloadable Ventra card to save on fares.


Instead of dining out every meal, opt for budget-friendly dining options. Explore local food trucks, try out popular street food like Chicago-style hot dogs, and visit neighborhood bakeries and delis for affordable yet delicious meals. You can also save money by cooking some of your own meals using local produce from farmers’ markets.


When it comes to accommodations, consider alternatives to traditional hotels. Look for deals on vacation rental websites or consider booking a room in a budget-friendly hostel. Staying in a neighborhood outside of the city center can often provide more affordable options without sacrificing convenience.


Make use of discount websites and apps to find deals on activities, attractions, and dining. Websites like Groupon and LivingSocial often offer discounted vouchers for various experiences in Chicago, ranging from spa treatments to boat tours.


Take advantage of free cultural events happening throughout the city, such as outdoor concerts, festivals, or art exhibitions. Check local event listings or the city’s tourism website to find out about upcoming events that align with your interests.


Consider joining loyalty programs or signing up for newsletters of local attractions and businesses. They often offer exclusive discounts and promotions to their members or subscribers.


Lastly, plan your staycation during the off-peak season. Prices for accommodations and attractions tend to be lower during weekdays or non-peak times of the year. By being flexible with your travel dates, you can take advantage of discounted rates.


Remember, a budget-friendly staycation in Chicago doesn’t mean sacrificing fun or memorable experiences. With a little research, planning, and creativity, you can enjoy the city’s attractions, dine at delicious eateries, and immerse yourself in the cultural offerings while keeping your wallet happy.



As you conclude your staycation in Chicago, you’ll likely have experienced the vibrant energy, diverse attractions, and rich culture that make this city a captivating destination. From exploring local attractions and landmarks to indulging in delicious cuisine and enjoying outdoor activities, Chicago offers a plethora of opportunities for relaxation, exploration, and entertainment.


By choosing the perfect staycation spot, uncovering hidden gems in different neighborhoods, taking part in cultural and artistic experiences, and immersing yourself in the city’s nightlife and entertainment scene, you’ve embraced the essence of Chicago and created lasting memories.


Throughout your staycation, you may have discovered that Chicago is a city that embraces both its iconic landmarks and its lesser-known treasures. From admiring architectural marvels to indulging in world-class cuisine, you’ve experienced the unique blend of history, art, and culture that this city has to offer.


Whether you’re a local resident or a visitor, Chicago is a city that invites you to dig deeper, explore further, and engage with the diverse range of experiences it provides. From its stunning parks and outdoor spaces to the world-class museums and theaters, there’s always something new and exciting to discover.


Moreover, by planning a budget-friendly staycation, you may have found innovative ways to enjoy all that Chicago has to offer while staying within your financial means. By taking advantage of free or discounted activities, exploring affordable dining options, and seeking out deals and promotions, you’ve shown that a memorable staycation in Chicago doesn’t have to break the bank.


As you bid farewell to the Windy City, take a moment to reflect on the experiences you’ve had, the moments of relaxation and enjoyment, and the joy of discovering what makes Chicago truly special. Whether it’s the vibrant street art, the flavors of deep-dish pizza, or the soulful tunes of live jazz, Chicago has left its mark on you.


Remember, Chicago will always welcome you back for more adventures and new experiences. So, until your next staycation, soak in the memories and carry the spirit of Chicago with you, wherever you go.