Celebrate Valentine's Day in Chicago (Updated 2026)

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks are...

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous past...

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold...

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience!...

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse...

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience...

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past...

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all...

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s...

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights...

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy...

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological...

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about...

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think...

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have...

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest...

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of...

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes...

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s....

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers....