Watch Chicago fireworks on a 90-minute tiki bar cruise
Paddle the Chicago River and learn downtown architecture in 3 hours
Stretch, cuddle, and play with rescue kittens in a 1-hour indoor class
Host a private kitten yoga party with playtime at The Arboretum of South Barrington
Paddle Chicago River routes in a single or double kayak
Paddle Goose Island and downtown as Chicago lights reflect on the river
Stretch, cuddle and take photos with rescue puppies in a private yoga session
Explore Lake Michigan’s quieter shore, from lakeside towns to grand mansions
Explore the history, neighborhood culture, and presidential ties of Chicago's South Side
Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours
Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide
See Chicago landmarks from the water on a private sightseeing outing
Photograph Chicago's skyline from a US Navy-built boat
See Chicago from the water aboard a former Navy tactical boat
Explore Chicago through social adventures with fellow solo travelers
Paddle Lake Michigan from Ohio Street Beach for two hours
Paddle Lake Michigan for Chicago skyline views
See holiday lights, market traditions, and Chicago's tree on a downtown stroll
Taste Chicago's holiday flavors and festive sights on foot
Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing
Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises
Bring your group aboard for a captain-led Chicago outing
Hire a Polish-speaking captain for your rented Lake Michigan boat