Want to get away without actually leaving town? A local staycation is a great way to explore your own city — you can revisit old favorites or try something new, all while supporting local businesses. Explore these staycation ideas for inspiration, then start planning your own Chicago experience. And don’t forget to book a hotel room for an overnight stay — there are tons of great hotel packages and discounts all around the city right now.

Check out our Chicago staycation ideas and itineraries:

Romantic getaway in Chicago

Whether it’s for an anniversary or your first weekend getaway together, Chicago has tons of romantic spots for couples. Start your staycation with an interactive cooking lesson, followed by cocktails with a view. Then get some culture with one of the world’s most prestigious art collections and a taste of Chicago’s vibrant music scene.

A couple enjoys fondue and candlelight at Geja's Cafe
©Adam Alexander Photography 2019

Day 1

  • The Chopping Block in Lincoln Square is offering in-person cooking classes on their outdoor patio, with plenty of space for social distancing. Choose from a variety of classes and demos, including wine tastings, a New Orleans-style brunch, and a German feast on the grill. You and your sweetheart can learn some new skills and enjoy generous tastings of each dish.
  • After class, enjoy cocktails with a view at one of the city’s many rooftop and patio bars. The Violet Hour, one of the city’s most famous cocktail bars, has recently opened a new outdoor space to sample their top-notch mixology. Near downtown, Three Dots and a Dash brings the tiki vibes to their new patio and The Laurel Room is a chic and airy rooftop space that feels like a California getaway.

Two women touring Chicago

Day 2

  • Grab some bites to go from a local restaurant and settle in for a scenic lunch at one of these top picnic spots. Check out spots like Ping Tom Memorial Park on the riverfront in Chinatown, near the historic boathouse at Humboldt Park, or Promontory Point with sweeping lake views in Hyde Park.
  • After lunch, visit the newly reopened Art Institute of Chicago. Even if you’ve been before, the museum’s massive collection means there’s always something new to see. Wander through their famous Impressionist rooms (one of the largest collections outside of The Louvre in Paris) before checking out their recently extended special exhibit El Greco: Ambition and Defiance.
  • For dinner, cross one of Chicago’s most romantic restaurants off your bucket list. Dine in a hidden garden on the patio of Piccolo Sogno, or enjoy a Michelin-starred tasting menu at minimalist Elske (the name of the restaurant means “love” in Danish). And Geja’s Cafe in Lincoln Park is a classic for couples — the fondue spot bills itself as the most romantic restaurant in Chicago, with hundreds of proposals each year.
  • End your evening with a nightcap and some live entertainment at one of Chicago’s music and comedy venues. Catch local and national standup acts at Zanies in Old Town, outdoor concerts on the patio at City Winery’s West Loop location, or live jazz in River North at Andy’s Jazz Club.

Family staycation in Chicago

Summer vacation might look a bit different this year, but that doesn’t mean you can’t create lasting memories. Plan a family-friendly staycation that hits all the right notes with kids and parents alike — interactive museums that are fun and educational, top attractions with breathtaking views, and drive-in movies theatres playing old-school favorites the whole family will love. Plus, Chicago museums and attractions have adopted new health and safety practices, like enhanced cleaning and social distancing measures, so you and your family can feel safe wherever you go in the city.

A family at Navy Pier
Photo by Ranvestel Photographic

Day 1

  • First, head to one of the most family-friendly places in Chicago — Navy Pier. There’s a reason it’s one of the top tourist destinations in the Midwest, and even locals will find something to love. Take the kids to watch the waves on the lake, see the jumping fountains in the Crystal Gardens, and enjoy live music along the waterfront.
  • Next, hop on one of the many sightseeing cruises that launch from Navy Pier. Take your pick from high-speed thrill rides to informative architecture tours to awe-inspiring tall ships. Afterward, get lunch with a lake view at one of the Pier’s many kid-friendly restaurants.
  • Keep your tour of Chicago’s top attractions going with a visit to one of the city’s sky-high observation decks. At 360 CHICAGO, the kids will love the heart-pounding TILT ride, you’ll love the bar with locally inspired cocktails — and the special ticket offers. All month long, youth tickets are free with adults and locals get 50% off admission. And Skydeck offers the jaw-dropping Ledge experience, where you can step onto a clear balcony more than 1,000 feet above the ground.
  • For dinner, pick from one of Chicago’s best family-friendly restaurants. There’s kid-sized pizzas at Lou Malnati’s, drive-in fun at Superdawg, and a whole sports museum attached to Harry Caray’s 7th Inning Stretch.
A girl explores an exhibit at the Museum of Science and Industry
Photo by Adam Alexander

Day 2

  • Start day two of your staycation with a visit to the animals at Lincoln Park Zoo. Meet creatures from all over the world in their outdoor exhibits, including lions, zebras, kangaroos, giraffes, rhinos, monkeys, and more. And don’t forget to check out the thriving wildlife around the Nature Boardwalk just south of the zoo. The free zoo has implemented timed reservations for all guests in order to support social distancing. Time slots fill up quickly, so make sure to plan in advance.
  • Next up: Museum Campus. Take your pick from some of the city’s most beloved (and family-oriented) museums. Tour a submarine and stand inside a tornado at the Museum of Science and Industry (and enjoy free admission through Aug. 14). Watch dolphins and touch stingrays at the Shedd Aquarium. Or meet an in-the-flesh version of the famous SUE T.rex for a limited time at the Field Museum. All Chicago museums are operating with limited capacity, rigorous sanitation, and plenty of social distancing — check museum websites for more details.
  • End your staycation with a classic drive-in movie experience. Near Museum Campus, CHI-Together at Soldier Field screens family favorites and cult classics — upcoming shows include Transformers, Spider-Man: Into the Spider-Verse, The Karate Kid and more. The pre-show entertainment includes live music and each car gets a free bag of popcorn. Or check out other drive-in and outdoor movie screenings all around Chicago, including free movies in the parks.

Friends weekend in Chicago

For the perfect staycation with friends, you’ll want a mix of bucket-list Chicago activities and some new adventures. For day one, cover the classics with some baseball and kayaking. For day two, pick a new neighborhood to go out and explore. Try checking out somewhere you haven’t spent much time in — Pilsen, Andersonville, Hyde Park, Chinatown, and West Town are all excellent options with tons of things to do. Once you’ve made your choice, use this itinerary as a template for a perfect day out. 

Day 1

  • Start your staycation with some light exercise and gorgeous views with kayak rentals on the Chicago Riverwalk. Urban Kayaks offers one- or two-person kayaks, so you and your friends can paddle on your own or join an informative architecture tour. Don’t feel like breaking a sweat? Check out the affordable and easy-to-drive Chicago Electric Boats.
  • Afterward, grab a drink on the many Riverwalk bars, like City Winery or Island Party Hut.
  • If you’re looking for a splurge, check the Chicago Cubs schedule to see if there’s a home game. While Wrigley Field is still empty, you can get a birds-eye view from one of the surrounding Wrigley rooftops. Capacity is limited, making ticket prices steeper than usual. But it’s a fun, all-inclusive experience if you’re looking for a way to make your staycation special. (The Chicago White Sox are also back in action. Watch the game in the beer garden at The Ballpark Pub.)
  • If baseball isn’t your thing, plan a walk-up window bar crawl with your friends. Chicago recently legalized to-go cocktails, opening up a whole new world of drinking possibilities. Just pick any neighborhood with lots of bars and restaurants close together — Boystown, Pilsen, Old Town, River North, and West Loop are all excellent candidates. A few can’t-miss stops: boozy snow cones from Ina Mae Tavern in Wicker Park, Japanese-inspired cocktails from kumiko in West Loop, and the large-format palomas for groups from Tanta. Check out this Instagrammer’s “to-go drink” highlight for more walk-up window bar crawl ideas.
Drinking beer on the ERIS patio
Sip house-made cider from ERIS Brewery in Irving Park.

Day 2

  • Start your day of neighborhood exploration off strong with a solid brunch on a patio. A few of our neighborhood favorites: Dusek’s Board & Beer in Pilsen, nana in Bridgeport, Longman & Eagle or Lula Cafe in Logan Square (Lula has a walk-up window where you can order food and bottled cocktails to enjoy in the park across the street). After brunch, pop into some neighborhood boutiques and bookstores to support local businesses, while scoring some cool stuff for yourself.
  • Chicago is a craft beer city, and much of that comes from the vibrant neighborhood breweries. Get to know a new area by exploring it’s local brew scene with these DIY neighborhood brewery tours. We’ve got guides for a tasting tour around West Loop & West Town, Pilsen & Bridgeport, Lincoln Park & Lakeview, Ravenswood, Beverly, and more.
  • Time for a little fresh air. Pick an outdoor space in your chosen neighborhood and go explore. Some great options include Garfield Park Conservatory, Jackson Park with the gorgeous Osaka Garden, the elevated 606 trail, and more.
  • End the night with cocktails and cool vibes. Enjoy the casual backyard feel at Sportsman’s Club in Ukrainian Village, fried chicken and frozen slushies at Parson’s Chicken & Fish in Logan Square and Lincoln Park, or beer and sausage at Kaiser Tiger in the West Loop.

Get your CityPASS
Planning a future trip to Chicago? Experience the city’s famous attractions at a 50% savings with Chicago CityPASS. Take your time and enjoy each attraction with 9 consecutive days to use your tickets. Rest assured that should your plans change, you’re covered by flexible 365-day risk-free returns. Trusted by 23 million travelers for 23 years. Includes prepaid admission to 5 must-see attractions:

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Go Chicago
Save up to 55% admissions to Chicago’s top attractions with Go Chicago. Explore Chicago at your own pace. Pay nothing at the gate — just use the pass on your phone or print it out in advance. No need to exchange money or hand over a credit card with contactless scanning at the attraction. The interactive mobile app will have you traveling around the city like a local! Choose from 25+ attractions, including:

  • Skydeck Chicago
  • Shoreline Architecture River Cruise
  • Hop-On Hop-Off Big Bus Tour
  • Art Institute of Chicago
  • Navy Pier rides
  • And so much more!

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