Fully private, fully customizable tours in Chicago — plus the top attractions to see, each with its own guide. Tell us what matters to you and we'll build the day around it.
Chicago sits on the shore of Lake Michigan and is widely regarded as one of the birthplaces of modern skyscraper architecture — a legacy still visible from Skydeck Chicago, the observation deck near the top of the Willis Tower, where glass floor boxes called The Ledge extend out from the building, 103 stories above the street. The Chicago Architecture River Cruise, consistently rated among the best tours of any kind in the US, takes that history to the water, narrating the city's building styles from a boat on the Chicago River.
In Millennium Park, Cloud Gate — universally known by its nickname, 'The Bean' — is Anish Kapoor's mirror-polished sculpture that reflects and distorts the skyline above it, and has become one of the most photographed public artworks in the world since its 2006 installation. Along the lakefront, Navy Pier adds a century-old pier turned entertainment district, with a Ferris wheel, gardens, and some of the best lake views in the city.
The Loop, Millennium Park, and Navy Pier sit within a few miles of each other along the river and lakefront, close enough that a private tour can combine the architecture cruise, The Bean, and Navy Pier into one well-paced day without backtracking.
Private Tours
A private, fully customizable tour of Chicago — Skydeck views, Cloud Gate, and a narrated architecture cruise along the Chicago River — in your own vehicle with a dedicated guide.
Private Tours
A private, skip-the-line guided tour of the Art Institute of Chicago — one of the largest and most respected art museums in the US, from Impressionist masterpieces to American classics.
Private Tours
A private, guided food tour through Chicago's neighborhoods — deep-dish pizza, Chicago-style hot dogs, and local spots chosen around your group's tastes.
Popular stops our guides build into Chicago itineraries — tap any attraction to learn more.
May through September brings Chicago's warmest weather and the best conditions for the Architecture River Cruise and Navy Pier's lakefront. Winters are cold, often well below freezing, with strong wind off the lake.
Downtown Chicago (the Loop), Millennium Park, and Navy Pier are close together along the river and lakefront — walkable in good weather, and easily combined by private vehicle for a full day that includes Skydeck Chicago as well.
Chicago is famously windy, especially along the lakefront and near Willis Tower's Skydeck — a windbreaker is worth having even in summer. Winters are cold with lake-effect wind chill well below the actual temperature.
The US dollar is used throughout, and 18–20% is standard tipping at restaurants. Contactless card and mobile payment are widely accepted.
Skydeck Chicago and the Architecture River Cruise both get busy in summer — booking timed tickets in advance avoids the longest lines, especially for The Ledge glass boxes at Skydeck.
The Chicago Architecture River Cruise is widely considered one of the best introductions to the city — even a short 90-minute cruise covers dozens of buildings and gives context you won't get from ground level alone.
Tell us your group size and dates — we'll take care of the rest.
