Tours and Activities

Chicago’s famous Pirates Pub Sail departs every Friday night at 9:00 p.m. aboard Tall Ship Windy at Navy Pier. Please arrive at least 15 minutes prior to departure. Your ticket includes up to four complimentary beverages per person: beer, soda or water.

SHARE THE MARVEL of maritime heritage on the Great Lakes! History comes alive with an exciting, educational adventure for curious minds of all ages. Join a local school or youth group on their sail training mission for hands-on sailing aboard the Windy.

A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago skyline.

Leave the hustle and bustle behind! Explore Chicago’s shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Available now. Offered daily May to September.

Join a local guide on this exploration of Chicago’s amazing food scene! The Loop is buzzing with activity, day and night, and your local guide will navigate you through the downtown streets straight to the vendors and restaurants they love most.

Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago, then we’ll hit the Central Loop, where locals go to grab their favorite foods.

Come along with a local guide to check out some of the must-see spots in downtown Chicago. You certainly can’t miss the soaring architecture that Chicago is famous for (you’ll be surrounded by it!) – and you’ll learn about the history of some of Chicago’s most well-known buildings.

A tour designed to hit some of Chicago’s must-see TV and movie filming locations may include a stops at locations from hit movies such-as the action-packed Dark Knight, the ’90s classic romantic comedy My Best Friend’s Wedding, and every kid’s dream, Ferris Bueller’s Day Off.

A private tour with Weventure Chicago is always a completely custom itinerary, created just for you and your group! A private city tour of Chicago can be from 4-8 hours, depending on the destination. Pick-up and Drop-off locations are the group’s choice.

On this Chicago tour, we make four stops at some of the best donut spots in the city. Along the way, we’ll try new and interesting flavors of donuts as well as discover the hidden donut history of Chicago. Get your tickets online now!

We will be starting this food tour at Robert’s Pizza & Dough Co. for an outstanding example of an artisan pie, then we walk to Labriola for one of the city’s best deep-dish pies; and finally, a Roman al metro at Bar Cargo.

Get to know more about the history of Chicago and its pizza culture as you eat! Learn more about the history of the West Loop as well and meet some of the characters, including the owner of a legendary Italian grocery store.

This tour’s highlights include a traditional Chicago deep-dish, a creative giant slice, a modern artisan neo-Neapolitan and a classic E. Coast slice.  Included in your tour price is a seasoned doughcent who will teach you about Chicago’s 10 styles of pizza, some history about Chicago, and more!

Unleash your inner street artist! This interactive workshop will allow you and your group the opportunity to create your very own original pieces. Plus, you’ll get aquatinted with the ins and outs of working with spray paint and stencil application.

Come see the hidden side of Chicago. This engaging adventure pops you in and out of beautiful buildings, familiarizes you with the most interesting parts of the famous underground Pedway, and shows you the best hidden details all over that people walk by every day.

Let Inside Chicago Walking Tours guide you away from the hustle and bustle of downtown Chicago, and into some of the most stunning interior spaces you’ll ever see — spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide.

The Diva Royale restaurant is the ultimate drag dining experience and Chicago’s #1 bachelorette party and gay bachelor party haven! The queens of Diva Royale love to host the hottest and best bachelorette parties, birthday parties and all kinds of celebrations!

Discover Argyle & Andersonville, two of Chicago’s best neighborhoods, on one tour! Enjoy foods from Vietnam, the Middle East and Sweden. Enjoy a savory tour with us as we take you through an immersive food tour experience including a glimpse of culture and history.