Best 317 things to do in Deerfield, IL

Paddle the Chicago River past the Wild Mile and downtown skyline

Paddle Chicago River routes in a single or double kayak

Build foundational kayaking skills on calm Chicago River waters

Paddle Goose Island and downtown as Chicago lights reflect on the river

Cruise Chicago by private 47 ft yacht with space for up to 12 guests

Cruise the Chicago River for 2 hours on a private, self-drive pontoon

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown

Ride Lake Michigan with downtown Chicago views

Explore Chicago's past with a private guide and museum admission included

Tour and tasting for two with a tasting room reservation and wine

Taste Chicago classics while exploring the city's landmark-filled streets

Taste Chicago donuts while uncovering Fulton Market’s industrial past

Trace Chicago's haunted lore, gangster history, and true-crime disasters on foot

Ride Chicago’s 1920s–30s gangster trail with actor guides

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

Taste Chicago’s donuts while uncovering the city stories behind each shop

Taste international dough-based treats while exploring Wynwood’s art district

Taste Santa Monica’s donut culture on an outdoor walking tour

Taste Dublin’s doughnuts while uncovering city stories on foot

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

Ride in a 2-seat supercar and capture your Chicago photo moment

Sample Chicago favorites while cycling through vibrant Near West Side neighborhoods on a fun 4-hour guided ride

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