37 Staycation Ideas In Chicago for Just About Everyone for 2025
Since so many people visit Chi-town every year as tourists, it only makes sense that locals might want to get in on some of the action and plan for a staycation in Chicago. If you have some vacation time planned out but want to stay closer to home, your very own city offers an array of fun things to do, no matter what you are interested in. They include world-class cuisine, performing arts, famous institutions, recreational opportunities and more.
The perfect staycation in Chicago allows you to relax on your home turf, but also explore parts of your own city you may not have seen or experienced. Whether it's a week of staycation or just a day, Chicago has so much to offer, you may never want to go anywhere else. Whether you live in the city proper or along its edges in the suburbs, there are many ways to enjoy a staycation in Chicago you may not have even considered.
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- Cheap Staycation In Chicago
- Staycation In Downtown Chicago
- Staycation In Chicago For Families
- Staycation In Chicago For Couples
- Staycation In Chicago FAQs
Cheap Staycation In Chicago
1. See the Stars at Adler Planetarium
The Adler Planetarium hosts weekly free nights during the Summer, which offer free basic admission to the museum and a chance to add additional perks like beautiful sky shows in their rounded dome theater. Take in the nearby Field Museum of Natural History or the Shedd Aquarium earlier in the day, or make a night of it with tacos at the 12th Street Beach stand and city views off the promontory for a fun and easy staycation in Chicago.
2. Visit the Lincoln Park Zoo
The north side’s Lincoln Park is home to one of only a handful of remaining free zoos in the U.S, which makes a great budget-friendly idea for a staycation in Chicago. Pair a visit with lunch at Lincoln Park Zoo’s food court with ample outdoor seating, or get lunch on the bustling nearby Clark Street. You can also bring a picnic lunch to have in the park or eat lakeside at the Theatre on the Lake. Other nearby sites that are great for staycationing include the Lincoln Park Conservatory, the Peggy Notebaert Nature Museum and the Chicago History Museum, all within walking distance from the zoo.
3. Outdoor Film Screenings
Each summer, both Millennium Park and the Chicago Park District host outdoor film screenings of classic and romantic movies. For a cinematic staycation in Chicago, watch a movie in Pritzker Pavillion with the city’s night time landscape in view or dip into one of the quieter neighborhood parks for smaller screenings from the Movies in the Parks series, which extend all Summer and are offered in almost all Chicago neighborhoods.
4. Free Musical Performances in the Parks
While the Millennium Park’s Summer concert season goes all season long with free weekly performances, you can also catch many other free or cheap performances outdoors throughout the Downtown area and out in various neighborhoods. Add in festivals like Chicago Blues Festival, Lollapalooza and street fairs for even more outdoor music options for your staycation in Chicago.
5. Chicago Public Library’s Winter Garden
In addition to a wealth of collections and resources, the Harold Washington Library Center is a beautiful architectural marvel on its own, known for its giant blue owls that perch like gargoyles at all four corners of the large block-spanning structure. The Winter Garden on the top floor is a great place to enjoy some sun all four seasons and is perfect for lounging, people watching or reading during your staycation in Chicago.
6. Take a Water Taxi Ride
While boat tours on the lake and river can be expensive, a lesser known and more budget-friendly option can be found in the local water taxis, which ferry you about to various city locales via the lake and river for on lonely $10 a ride (with an even better deal for a 10 ride pass for only $25.) Stops include Navy Pier, the Loop, Chinatown and the Museum Campus.
7. Visit Chicago Park District Locations
The Chicago Park District has locations, services and green spaces in every neighborhood in the city. Many larger parks boast historic field houses that offer classes, lessons and other programming for free. They are just one of many local places to find painting classes in Chicago or pottery classes in Chicago, including community centers, craft retailers and educational institutions.
8. Ride the Train
One of the best and most budget-friendly ways to see the city during your staycation in Chicago is to ride the elevated trains, transferring between lines downtown. Choose a line you don't usually take on your daily commute, like the Red line from end to end or chart the Green, Pink, Brown line to branch off in other directions. The Blue Line will take you all along the northwest corridor of the city and out to O’Hare Airport if you'd like to pretend you're going on a vacation out of the city.
9. Check Out Chinatown
This little pocket of the city has some of the best places to get Asian cuisine, including dim sum and Chinese delicacies and pastries. Wander the small shops and eateries or check out the Chinese American Museum in the afternoon. During the Lunar New Year, you can also enjoy Chinese New Year food, festivities with parades and performances.
10. Wander Art Galleries
Most Chicago art galleries offer free admission and are scattered throughout the city in various neighborhoods, some in clusters that make it easy to wander through a few in any one day without having to drive. Pair a local gallery crawl with dinner in nearby neighborhoods like River North or the Fulton Market District.
Staycation In Downtown Chicago
11. Visit The Fine Arts Building
If you love art, music or dance, check out what's happening at the Fine Arts Building during your staycation in Chicago. Located in the historic Studebaker building on South Michigan Ave, it contains ten stories of galleries, musical instrument craftsmen, dancers, music tutors and working artists. There is even a bookstore on the second floor and a sheet music retailer on the ninth Floor. Bring a lunch to enjoy in the building's center Italianate courtyard or see a performance at the Studebaker Theater in the bottom. It's also a great place to check out dance classes, art classes or photography classes in Chicago.
12. Take in a Show
Chicago is home to a number of amazing world renowned local theater and other performing arts institutions, including Chicago Shakespeare Theater, The Goodman Theater, The Joffrey Ballet and more. Broadway in Chicago also brings in a regular and varied schedule of touring Broadway productions mounted at beautiful historic theaters in Downtown. Pair theater tickets with a night at one of the Loop Theater District's many restaurants and bars for a complete staycation in Chicago.
13. Stay at a Historic Hotel
While this one can be expensive depending on the season and demand, booking a couple nights at one of the fancier historic Chicago hotels can be a great way to feel like a visitor in your own city. Great posh options include The Congress Hotel, The Hilton or The Blackstone Hotel, all of which offer park and lake views. Or go further into the loop to stay at The Palmer House or the Royal Allegro Sonesta for beautiful historic details closer to theaters and shopping. Or make a staycation night of luxe living at The Drake or The Warwick Allerton Hotel along the Magnificent Mile for a staycation in Chicago that favors shopping.
14. Take a Chicago Architecture Tour
These tours operate dually during the warmer seasons, offering a river-level view of the city with informed tour guides that explore history and the finer points of architecture along the river and lakefront. They even host nighttime tours that show you the city in all its glittering beauty. Or, take a dinner cruise on the lake or river for an evening of music and sightseeing.
15. Visit The Art Institute
The Art Institute of Chicago is world-renowned for its huge collection of art and artifacts, including famous Impressionist paintings from Monet and Renoir, as well as touring collections from artists of many eras. The beautiful and sprawling museum also hosts exhibits devoted to furniture and architecture, design and textiles. Have lunch in the museum’s eateries or head across the street to one of the many cafes and bars for lunch or dinner after your visit. Or, visit the Museum of Contemporary Art just off the famous Magnificent Mile for a complete artistic staycation.
16. Haunted Chicago History Tours
Chicago is a city filled with ghosts and haunted history, from the famous Eastland disaster victims that haunt the riverfront to local cemetery lore and vanishing hitchhikers. You can take a walking tour of many of Downtown’s most famous haunted locations or take a bus tour to some other far flung spooky spots around the city like Hull House, the site of the St. Valentine's Day Massacre or the suburban Resurrection cemetery of Resurrection Mary fame.
If you don't know the history of this famed hitch-hiker, Resurrection Mary is Chicago's legendary "vanishing hitchhiker" ghost. She's a blonde woman in a white dress, appearing along Archer Avenue and waves down drivers near Resurrection Cemetery. Mary then vanishes from the sight, sometimes even after the door has been opened. The ghost is thought to be the restless spirit of a young woman who died in a hit-and-run accident in the 1930s and is buried in the cemetery. Her exact identity is debated.
Fun options include Chicago Ghosts and Gangsters and Windy City Ghost Tours.
Staycation In Chicago For Families
17. Bumper Car & Bowling Fun at Whirlyball Chicago
Great hijinks for the whole family, this cross between basketball, lacrosse and old-school bumper cars is sure to be a hilarious hit, either as a family endeavor or as a fun team building activity in Chicago. The Whirly Ball courts also have other adjacent activities like arcade games, laser tag, bowling, food and an extensive bar available in their Lincoln Park spot.
18. Explore Navy Pier
This famous attraction in Chicago has something for everyone, including the ferris wheel and carousel, the Chicago Children’s Museum, the Chicago Shakespeare Theater, boat tours, outdoor events and concessions and the largest rooftop bar in Chicago — Offshore Rooftop. It also houses a hotel at the end of the pier and the best views of the skyline you can get.
19. Street Festivals and Block Parties
Throughout Summer and early Fall in the city, you can find corridors of streets blocked off, some with carnival attractions, large stages and vendors. Listen to live music and enjoy barbecues, corn dogs and kids activities. You can also get to know your neighbors in small celebrations throughout the various neighborhoods. Find a complete list for the season at Choose Chicago.
20. Bike Along the Lakefront
Ride your own or rent a bike to enjoy the long lakefront trail system. Add in a picnic and stop with a view of the water for lunch. Or dine at many of the small food stands and trucks that line the sprawling path in warmer weather. You can literally ride from one end of the city to the other, starting in Edgewater and continuing to the far south side Hyde Park. Tandem bikes and trolley bikes are also available for rent for Chicagoans who don't own bikes.
21. Sporting Events
Sports are a way of life in the city with a multitude of professional teams in all sporting genres, including Cubs/White Sox baseball, Bulls basketball, Bears Football and Blackhawk hockey.
Or go smaller with minor league and non-league games and gatherings throughout the city in venues and parks which make a great outing for a Summer or Fall day. You can also enjoy various conferences and events that cater to certain franchises like Bears and Cubs draft celebrations.
Staycation In Chicago For Couples
22. Arts & Crafts Day
If you and your better half are into arts, crafts or DIY, check out some of the city's wealth of art stores, craft shops and home improvement stores. Great stops include Blick Art Materials downtown Randolph Street location or Humboldt Park’s The Waste Shed, offering discounted secondhand supplies. Or take a candle-making class in Chicago. There are also a number of small boutiques throughout the city that specialize in handmade goods, like Andersonville’s Milk Handmade or Westown’s One Strange Bird. These hops are also a great spot to pick up Chicago gifts — to support local or for visiting friends.
23. Paint and Sips
Paint and sips are a fun way to learn and enjoy creating together while having a few cocktails. This makes them perfect for first dates or for long term partnerships. Find paint and sip classes in Chicago with typical programming based around a theme, subject, artist or special occasion for artmaking.
24. Chicago Brewery and Distillery Tours
There are a number of local breweries and distilleries that offer tours, tastings and other events that make a boozy good staycation visit. You can learn about brewing and manufacturing while trying out various craft creations. Or take a mixology class in Chicago to get the skills to make your own unique cocktails at home. For spirits, visit Wolf Point Distilling or the KOVAL Tasting Room. For beer, must-visit breweries include Goose Island Brewery and Revolution Brewing.
25. Chicago Cooking Classes
You can find cooking classes offered by top chefs spanning all sorts of cuisines and topics of interest, including basic kitchen skills for new chefs and crazy culinary competitions for large families or groups of friends. Learn how to concoct the tastiest pasta or how to roll sushi. There are also cooking classes in Chicago devoted to classic Chicago foods like sausages, hot dogs and deep dish pizza. Cooking classes also make awesome experience gifts in Chicago.
26. Sneak Off to a Speakeasy
Chicago bars are fun, but you can capture the essence of a Chicago nightlife scene at one of the city's many speakeasies, some with more findable locations than others. Check out the alleys, back entrances and underground lairs, some of which offer cabaret and other kinds of regular performances. Your local tavern may even have a secret private speakeasy serving specialty cocktails and offering tastings in the back room. Great suggestions include Gatsby’s Speakeasy, The Drifter and Brando’s Speakeasy.
27. Learn About Chicago Improv
Chicago is famous for its improv theater that makes a great date idea in Chicago because you can get to know your partner more intimately through acting. Join as a participant by enrolling in a class at IO Improv or the famed Second City with infamous alumni like John Candy, Dan Aykroyd, Eugene Levy, Gilda Radner, Richard Kind, Mike Myers, Chris Farley, Tim Meadows, Bob Odenkirk, Amy Sedaris, Stephen Colbert — we have to stop somewhere. Or remain an observer by taking in any number of performances offered in the city in a given week. Most theaters offer food and drinks aplenty to enjoy during the show.
28. Antiques and Thrifting Afternoon
Many neighborhoods have an abundance of antique and thrift stores that are worth visiting if you love finding unique home decor, furniture and clothing eras past. Great options include Brown Elephant (with Lakeview and Andersonville Locations), Green Element Resale, Broadway Antique Mall and Woolly Mammoth (all in Edgewater.) Each Summer, you can also find outdoor antiques at the Randolph Street Market every weekend.
29. Go for Brunch
Brunch is a way of life for some in Chicago, so checking out the more famous and tastiest spots in the city can make a great addition to your Chicago staycation. If you're Downtown, check out spots like Wildberry Pancakes and Cafe, Beatrix or Yardbird for a bite or hit up neighborhoods like Wicker Park, Logan Square and Anderson. If you want brunch with a view, try Cindy’s Rooftop, one of the most famous Chicago rooftop restaurants right along Millennium Park.
29. Catch a Film at a Historical Cinema
Looking to see a movie during your staycation? If Summer has ended and you missed all the outdoor theaters mentioned earlier, there are still many great choices. While there are numerous modern multiplexes all over the city, you might want to take a bit more of a historical approach and visit some of the classic Chicago theaters that show modern showings of movies, like Logan Square’s Logan Theater or Lincoln Square’s Davis Theatre, both of which have been restored to their Art Deco era opulence fused with modern audience expectations (comfier seats, concessions, excellent sound) and boast multiple screens and event spaces.
31. Visit the City’s Literary Locales
Chicago is a city of writers, with many famous authors hailing from the city like Gwendolyn Brooks and Carl Sandburg. This means Chicago also has a wealth of literary institutions, including The Poetry Foundation's large facility that hosts readings/events and houses a vast library of poetry titles. Or, visit the Chicago Writers Museum on Michigan Ave. Check out weekly performance poetry and spoken word at the famous Green Mill Lounge in Uptown, the home of slam poetry.
Staycation In Chicago FAQs
What Is The #1 Tourist Attraction In Chicago?
While Chicago has many famous attractions, depending on what interests you, many consider the sprawling Millennium Park to be the top attraction that draws the most visitors each year. Millions flock to see the famous “Cloud Gate” sculpture by Anish Kapor (a.k.a., “The Bean”). They also come to enjoy ice skating, music performances, green spaces and other public art pieces all perched between the bustle of Michigan Avenue and the lakefront.
Where Can I Sleep For A Few Hours In Chicago?
If you just need to crash for a few hours or find a place to rest in proximity to your destination, there are a number of local hotels listed on Dayuse.com that will allow you to rent rooms for a few hours at a time or offer rates for designated blocks of time. There are also hostels in the city that offer affordable beds at discounted rates for travelers, which can also be a great place to catch some Zs if you don't want to rent an expensive downtown room overnight.
Whether you are new to the city or a long time resident, these Chicago staycation ideas are perfect for a wide variety of interests and schedules. Use one or combine several for an active staycation that will make you feel like you are visiting for the first time.
For even more fun gift ideas in the Chicago area, check out other experiences happening on Classpop!
