Best results for Tours And Adventures in Chicago IL

Cover Chicago's icons in 2 hours with a guide, from the Magnificent Mile to Millennium Park.

Taste Chicago classics and explore top landmarks on a guided 5-hour tour

Explore masterpieces with a private guide and skip the ticket lines.

Explore the hidden Pedway and stunning interiors while uncovering quirky stories beneath downtown Chicago

Explore hidden architectural gems and ornate lobbies with a guided 2-hour stroll through the Loop

Explore Chicago’s darker past with ghost stories, gangster lore, and true crime on a relaxed 2-hour city walk

Explore Chicago’s glamorous Art Deco interiors with stories of the Roaring ’20s

Taste top donuts and uncover sweet history on a 2-hour downtown walking tour

Sample creative donuts and hear West Loop stories on a 2-hour guided stroll

Experience Chicago as it was during the 1920s and 1930s!

Skip lines and explore masterpieces with an expert guide in a small group for a more personal, flexible visit

Savor a donut and enjoy 103rd-floor views as you learn how Chicago rose from the Great Fire

See Chicago's top landmarks by air on a private, air-conditioned helicopter flight

Taste top donuts and beignets as you explore Magazine Street history in a 2-hour walking tour

Taste baked and artisan donuts across West Hollywood on a relaxed 2-hour stroll

Sample delicious donuts as you explore historic DC landmarks

Sample Miami favorites and explore Wynwood Walls on a guided 3-hour food and art walk

Sample donuts and churros as you explore Wynwood's art scene on a 2-hour walk

Taste signature donuts while exploring Harvard Square's history

Sample iconic Brooklyn donuts on a 2-hour walk through Williamsburg and Greenpoint

Taste classic and artisan donuts while exploring East Village landmarks and music history

Taste standout donuts while exploring Times Square and Rockefeller Center with a local guide

Taste top donuts while exploring Union Square and Greenwich Village

Taste top donuts and explore Philly's sweet spots on a guided downtown stroll

Taste top donuts and uncover sweet local history on a 2-hour walking tour

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

Discover Chicago's iconic skyline and rich history on a narrated lake and river cruise

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing

Charter a 47 ft yacht to cruise the Chicago River or Lake Michigan with BYOB and skyline views

Captain your own pontoon on the Chicago River for two hours with training and life vests provided

Drive your own pontoon on the Chicago River with BYOB and a quick lesson

Sail past the Chicago skyline on a 2-hour 21+ cruise with drinks for purchase and Thursday brewery or Friday live music

Discover Chicago architecture and fireboat history on a guided river cruise.