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.
Day 1
- The Chopping Block in Lincoln Square is offering in-person cooking classes, 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. Or get cozy on a heated restaurant patio, like the cool dining domes at Beatrix in the West Loop.
Day 2
- If it’s nice outside, 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 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 Sognoand 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 or Laugh Factory, see a drag show at Baton Show Loungeor burlesque at Bordel, or live jazz in historic surroundings at the Green Mill.
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.
Day 1
- First, hop on one of the many sightseeing cruises, a great all-ages way to see the city’s top sights.
- 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.
- For dinner, pick from one of Chicago’s best family-friendly restaurants. There’s kid-sized pizzas at Lou Malnati’sand drive-in fun at Superdawg.
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 at ChiTown Movies in Pilsen. They screen everything from family favorites to cult classics, plus you can order snacks to your car.
Local daycation in Chicago
The best way to make a staycation feel like a vacation is by getting out there and exploring a different area of the city. So 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.
- Start your day of neighborhood exploration off strong with a solid brunch. A few of our neighborhood favorites: Pilsen Yards in Pilsen, 90 Miles Cuban Cafe in Logan Square, and Osito’s Tap in Little Village.
- 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 Park & Field in Logan Square, housemade cider at ERIS Brewery and Cider House , or beer and sausage at Kaiser Tiger in the West Loop.
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!
Explore Go Chicago options:
Go Chicago — All Inclusive
Go Chicago — Explorer
Go Chicago — Build Your Own
