Summer staycation in Chicago: ideas for families, couples, and more

Want to get away without going too far? A Chicago staycation is a great opportunity to revisit old favorites or try something new, all while making the most of your summer.

Explore these Chicago staycation ideas with inspiration for couples, families, and locals. And don’t forget to book a hotel to make it a true summer getaway.

Check out our Chicago staycation ideas and itineraries:

Family staycation weekend in Chicago

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 kid-friendly restaurants that the whole family will love.

Staycation highlights:

• Kick off the weekend on the water with a sightseeing cruise.
• Explore one of Chicago’s unique interactive museums.
• Wow the whole family at the city’s sky-high observation decks.
• Enjoy bites from family-friendly restaurants and top ice cream shops.

Day 1: sightseeing cruises and skyline views

• First, hop on one of the city’s many sightseeing boat cruises, a great all-ages way to see Chicago’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 Skydeck Chicago, kids will love the hands-on exhibits in the first-floor museum and the jaw-dropping views from the 103rd floor.
• Let the kids run wild at one of Chicago’s interactive museums, from the sensory Sloomoo Institute for tots to the Instagram-friendly WNDR Museum for tweens and tweens.
• For dinner, pick from one of Chicago’s best family-friendly restaurants.

Day 2: wild animals and running wild in downtown parks

• Start day two of your staycation with a visit to the animals at the free Lincoln Park Zoo, where you can meet creatures from all over the world, including lions, zebras, kangaroos, giraffes, rhinos, monkeys, and more.
• Next up: head to the Field Museum for the Summer of SUE. Chicago’s iconic natural history museum is celebrating 25 years of SUE, the most complete and largest T. rex ever discovered. Find Summer of SUE events all season long.
• Head downtown to blow off some steam at Maggie Daley Park, a lakefront wonderland for kids of all ages. Or cool off in Crown Fountain, an interactive splash pad in Millennium Park.
• End your summer staycation with a sweet treat from one of Chicago’s top ice cream shops.

Explore more: Find top things to do with teens and tweens in Chicago.

Romantic summer getaway in Chicago

Whether it’s for an anniversary or just because, couples will find plenty of romantic spots for a summer getaway in Chicago. Start your staycation with an interactive cooking lesson, followed by cocktails with a view. Then enjoy the city’s sparkling waterfront and get a taste of the vibrant music and nightlife scene.

Staycation highlights:

• Learn a new skill together with fun classes and workshops
• Soak in the sun on rooftop bars with a view.
• Grab tickets to a top music venue or comedy club.
• Make reservations for one of the city’s most romantic restaurants.

Day 1: cooking classes, rooftop cocktails, and live comedy 

• Start your weekend by learning something new with one of the city’s fun classes and workshops, like blending your own custom candle scent at Embers + Apothecary Co. or crafting handmade pasta at Tutore Italian Cooking School.
• After class, enjoy cocktails with a view at one of the city’s many rooftop and patio bars. The newly revamped Solana offers poolside margaritas in Wicker Park, while VU Rooftop features stunning skyline views from the South Loop.
• End your evening with a nightcap and live entertainment at one of Chicago’s top live music and comedy venues. Catch improv at The iO Theater, enjoy dinner and a show at cabaret-style Teatro ZinZanni, or hear live music at Winter’s Jazz Club or The Redhead Piano Bar.

Day 2: retro boat rides and romantic eats

• Make the most of a beautiful summer day with a morning stroll in one of the city’s most romantic parks. Wander around historic lagoons in Humboldt Park, admire blooming flowers in Lincoln Park, or walk the elaborate gardens in and around the Garfield Park Conservatory.
• Impress your date by renting a vintage boat and cruising down the Chicago River. The retro rides from Chicago Boat Company are outfitted with electric motors, making it easy to captain a romantic voyage with breathtaking skyline views.
• Step back in time at the Driehaus Museum, a Gilded Age-era home filled with ornate marble, antique furniture, and stunning stained glass.
• End the day with a Big Bus Chicago Sunset Live Tour, which offers panoramic views of the city as you cruise around during golden hour.
• For dinner, cross one of Chicago’s most romantic restaurants off your bucket list. Enjoy Michelin-level cuisine and cocktails at After, soak in the chic atmosphere at Bronzeville Winery or Maxwells Trading, or split a plate of pasta at Mano a Mano.

Local summer staycation for Chicagoans

The best way to make a staycation feel like a vacation is by getting out there and exploring a different area of the city. This itinerary covers a wide range of Chicago neighborhoods, from theatre districts staging unique productions to culturally rich enclaves filled with one-of-a-kind museums. 

Staycation highlights:

• Brunch and boutique shopping in Andersonville.
• A craft brewery crawl in Ravenswood.
• Dim sum and bubble tea in Chinatown.
• Culture and outdoor space in Hyde Park.
• Dinner and drinks in Bridgeport.

Day 1: brunch and craft brews

• Start the day with brunch and shopping in the quirky Andersonville neighborhood, known for its abundance of local boutiques and eateries. Top brunch options include Southern fare at Big Jones, Middle Eastern cuisine at Fiya, Taiwanese dishes at Minyoli, and more.
• Next, wander over to Malt Row to sip your way through some of the city’s best craft breweries and distilleries. Make sure to hit Begyle Brewing Company and KOVAL Distillery.
• Enjoy an early dinner at one of Rogers Park’s many international dining options, like Khmai Cambodian Fine Dining, Mango Pickle, Badou Senegalese Cuisine, and beyond.
• Grab tickets to see a show in the Edgewater Theatre District, home to unique local venues like TimeLine Theatre, City Lit Theater Company, The Edge, Redtwist Theatre, Steep Theatre, and more.

Day 2: dim sum and under-the-radar museums

• Start your day off with a dim sum brunch in the Chinatown neighborhood. Bonus points if you take the water taxi from downtown.
• Walk off brunch at lakefront Jackson Park, where you can wander through the Osaka Garden, an authentic Japanese garden from the 1893 World’s Fair.
• Explore one of the many museums and historic attractions in the Hyde Park neighborhood, like the Robie House (a UNESCO World Heritage Site), The Renaissance Society, the Smart Museum of Art, the Institute for the Study of Ancient Cultures, and more.
• Head to Bridgeport to grab a bite to eat at Kimski, serving Korean-Polish fusion, or The Duck Inn, known for their rotisserie duck and duck fat hot dog.
• End the day with a drink on the patio at Maria’s Packaged Goods & Community Bar or listening to curated vinyl selections at Charis Listening Bar.