Best 124 things to do in Deerfield, IL

Eat a donut, then head up to the Willis Tower Skydeck

Walk the Chicago Loop to see hidden interiors and Millennium Park

Cruise the Chicago River on a private boat with local architecture stories

Cruise the Chicago River for skyline views and Riverwalk sights

Sail Lake Michigan on a private day charter with skyline views

Cruise about two miles offshore for wide-open Chicago sunset views

Speed across Lake Michigan with your own music and skyline views

Cruise offshore from Navy Pier for fireworks and skyline views

Sail Lake Michigan for Navy Pier fireworks views on a private charter

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft

Fly over Chicago landmarks with a private helicopter for up to 3

Take the controls in a 30-minute helicopter intro flight

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

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

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

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Eat your way through Chicago’s Chinatown with 5 seated tastings

Walk Pilsen for tacos, cocktails, and mural-filled streets

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Paddle the Chicago River and learn downtown architecture in 3 hours

Night kayak tour to watch Navy Pier fireworks

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