things to do in Oakbrook Terrace, IL

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Step inside Chicago Loop landmarks and trace the evolution of its skyline

Taste your way through Chicago’s West Loop with a local guide

Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio

Get your bearings on your first day in Chicago

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion

Taste Dublin’s doughnuts while uncovering city stories on foot

Create a one-of-a-kind poured-paint figurine

Take the controls in a 30-minute helicopter intro flight

Bike Miami Beach and sample local food with a guide

Hire a US Coast Guard licensed captain for your Chicago boat day

Cruise Chicago’s river in a vintage 1950s Milo Craft

Private skyline cruise with a local perspective

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Cruise a 47-foot Carver with space to relax, dine, and play your music

Explore the history, neighborhood culture, and presidential ties of Chicago's South Side

Take in Chicago's parks, waterfront, and landmark sights in one ride

Explore historic prison spaces at your own pace

Walk Edinburgh’s Old Town and sample doughnuts and pastries in 2 hours

Paint a doormat that matches your style

See Chicago's northwest suburbs and the Fox River from the air

Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks