There are those who understand that you can never really experience a city like a native until you’ve navigated her streets on foot, rubbed shoulders with her locals, and “pounded the pavement” from one community to the next, watching as each block transitions from residential to commercial or mixed use. Chicago’s neighborhoods almost demand an intimate exploration, and for those fit and prepared for the elements, a walking tour can provide the nearest experience to a local’s understanding of the Windy City.
Walking tours are an excellent way to keep up fitness over two, three, or even more hours of sightseeing. You’ll have an opportunity to directly interact with a guide who isn’t in danger of being distracted while driving, flying, or piloting a boat. If you want to step away a little from the group to take pictures, it’s fine- so long as you don’t wander off and get lost!
Tour operators want to make sure you experience exactly what you came to town to enjoy. Whether that’s delighting in the famous Midwestern cuisine on offer throughout the city or a knowledgeable description of the architectural achievements of architects past, your tour operator has something mapped out just for you. Just be sure you have sturdy, comfortable shoes and are not prone to exhaustion after a reasonably leisurely stroll.
Remember that whichever walking tour you choose, be prepared for the weather to change on a moment’s notice. It’s always a good idea to check the forecast before setting out for a stroll. Winter can be frigid, so dress warmly. Spring brings showers, so an umbrella and rain-proof shoes or boots can be a major travel benefit. Of course, the city is best known for its wind, so make sure your hats are securely and firmly on your head!
- Chicago Food Planet Tours: From the West Loop, Gold Coast, Old Town, Chinatown, or Navy Pier, you’ll get to know a neighborhood or two’s unique tastes.
- Chicago Greeter Tours: Meet an expert local volunteer, an energetic and informed person eager to show you their best Chicago as they know it.
- Chicago Detours: Step up to learn about architecture, food and drink, and special events; take on your favorite Chicago experience in stride with style!
- Inside Chicago Walking Tours: Go inside a few interesting buildings along the walking route at a leisurely pace near the Loop and River North.
- Tastebud Tours: Sample the most famous Chicago grills and bars, indulge in comfort food, and walk off the experience over three hours.
- Bobby’s Bike Hike: “Stroll instead of roll” on one of Bobby’s many hiking tours, including a tasty seasonal food sampling during the holidays.
- Chicago Architecture Center: With a mission to inspire visitors to understand why design matters, this tour focuses on the city’s numerous architectural masterpieces.