Exploring Chicago from New Perspectives: Walking and Cycling Tours of the City

Mar 14, 2023

Maybe you’ve been to Chicago regularly for work, or perhaps hit the city for a sporting event or parade, but no matter how many times you’ve visited, there’s always something new to discover! Today we’re highlighting some unique ways to explore the city up close and personal with unique walking tours and other fun activities.

Xperience Days Bike Tours of Chicago offer two different types of tours, day or night, for a 2 ½ to 3 hour cycling tour of the city! It’s perfect for your high energy travel companions, with a gorgeous outdoor experience of the city on the Linoln Park Tour. that tour stops by the Chicago LAkefront, Navy Piere, Lincoln Park Zoo, North Avenue Beach, and the Conservatory. The Night Tour takes you down the Magnificent Mile for gorgeous, sparkling views of the Chicago Skyline, stops at Crown Fountain, and fireworks at Navy Pier! Even Chicago natives are raving about how fun and interesting these locally guided tours are, so you know they’re great!
Bobby’s Bike Hike Tours of Chicago have been the USA’s longest running bike tour company, and offer a wide variety of bike and walking tours of the Chicago area. No matter your age or skill level, there’s a tour for you! You’ll get a new perspective on the Chicago Metro Area, learn about its history, and have some delicious local Chicago Favourites to eat.

Bikes, Bites, and Brews by Bobby’s Bike Hikes offer a cycling tour of Chicago’s best neighborhoods and top eateries! You’ll take in the sights, learn about local history, and chow down on the most delicious grub including pizza, hot dogs, cupcakes, and beer! Bike rental, helmet rental, water bottle, and samples of food are included in the cost.
Chicago’s West Side Foodie Bike Tour is a half-day cycling experience through the city exploring Chicago’s architecture while stopping off for some incredible food tastings. You’ll experience a wide variety of local ethnic foods and drinks, and all tastings and drinks are included in your rental price. From Polish food to Mexican food to locally crafted chocolate and more, you’ll have a blast!
Free Chicago Walking Tours are led by local guides who know the neighborhoods inside and out for free public tours or reasonably priced paid private tours for groups of more than 6 and up to 20! (Tipping your guide is recommended, especially on the free options.) This group’s tours are perfect for those who do not want to do endurance training via sightseeing, because they’re just 1 to 3 miles in distance! It’s the perfect option for those with kids and teens, because it’s just the right amount of time. It’s a great way to make new friends and socialize with locals and tourists alike. Click here to learn more about upcoming tours or schedule a private group!

Bizarre Bucktown is where it’s at if you’re looking for interesting, quirky, and memorable experiences of Chicago. It doesn’t matter how many times you’ve been to the city, you’ve never seen it like this! On your 90 minute walk with a small, intimate group of folks, you’ll learn about the history and hauntings of Bucktown and Wicker Park. Tickets are just $15 per person, but the memories are priceless; click here to book your tour!
Chicago Prohibition Tours in Chicago offers both bus guided and walking tours exploring Chicago’s storied history during The Prohibition Era. You’ll visit many of the area’s historic speakeasies, and become a “scofflaw” as you learn about the history of politics, gangsters, and Prohibition crimes. You’ll love that it’s coupled with great food and drinks along the way on your 3 hour trek or 2 ½ hour bus tour.Chicago Architectural Center Tours offers a 90-minute walk through tour highlighting the most famous buildings in Chicago, and the history and stories behind their inspiration and design. This wonderful nonprofit organization aims to inspire new generations of architects and designers. The city also has numerous options for walking, bus, or boat architecture tours if you are further inspired by the CAC’s exhibits and programs
Chicago Detours Walking Tours offer a personal and up close look at the different neighbourhoods around Chicago! You will be invited to learn about the history, food, and culture of the city while connecting with local businesses and enjoying some sightseeing. You’ll take “the roads less traveled” and explore the city from a local’s perspective, and see the city like never before.