On a boat
If you’re not ready to party in the Playpen or mix with tourists on an architectural boat tour, your crew can still cruise this summer. Check out the Chicago Electric Boat Company, which lets you rent vessels tailored to novice skippers. Choose from a fleet that includes 18-foot picnic boats with canopy tops, doughnut-shaped rigs with roundtable seating ideal for gazing at architecture, and 1950s-style cruisers in cool retro colors. From $900 an hour for up to 13 people. chicagoelectricboats.com
At the bowling alley
Following a long coronavirus-induced hibernation, Avondale Bowl reemerged as chill and Instagrammable as ever, but with half of the lanes closed to allow for social distancing and stringently disinfected shoes and balls. Go big and rent the whole shebang — you’ll have reign of the lanes and dedicated servers to ensure everyone has a drink in their nonbowling hand. Private parties for up to 50 people, from $350 per hour (includes shoe and lane rental). 3118 N. Milwaukee Ave.
At a vacation pad
Yes, you and your pod can responsibly staycation together, thanks to Airbnb options like a baller penthouse loft in Old Town. Two separate units adjoined by a private staircase make up the roomy 4,000-square-footer. Grownups can mingle freely while the unvaxxed kids watch Netflix in their own space, then convene for open-air shenanigans on the rooftop deck. From $799 a night for up to 16 people. airbnb.com/rooms/16453692
In a secret garden
While jetting off to the Piedmont region may not be in the cards quite yet, a cozy family-style Italian feast at Osteria Langhe can temporarily scratch the pasta-and-wine itch. Rent the entire lush patio for a dinner party and your whole group can gather around the single large table to enjoy a preset meal with wine pairings. $1,200 minimum on food and drink for up to 14 people. 2824 W. Armitage Ave., Logan Square
At the beach
Twelfth Street Beach may not be as prime for people-watching as its North Side counterparts, but this summer, that’s a good thing: There’s a greater likelihood of your group finding ample towel space here. Plus, the skyline view is stellar. 1200 S. Linn White Dr., Near South Side