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:

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:

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

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:

Day 1: brunch and craft brews

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