Growing up in rural Illinois, I could drive at night through cornfields like a pro, but I could not tell you what came on a Chicago-style hot dog. Any urban setting felt like an entirely different world to me. Until I started living in the city myself did I begin getting to know, and love, Chicago. And while there is no shortage of tours that show off the city’s world-famous architecture, iconic foods, and mobster history, the best walking tour in Chicago actually gives you all three.

This tour is perfect for first-time visitors who want to experience what the Windy City is most known for — plus little-known spots precious to locals. Whether you're coming in from another part of Illinois, another state, or another country entirely, this walking tour gives you a taste (literally) of some of Chicago's best attributes.
best walking tour in Chicago
John Picken, CC BY 2.0 , via Wikimedia Commons
For about $108 per person, the tour includes a guide, tasting five different food samples at five different locations, transportation, tips on what else to do while you're in town, and plenty of architectural sightseeing.
The 5-hour tour begins in the heart of Downtown under the iconic Chicago Theatre marquee on State Street. Pro tip: Make sure to wear comfy shoes!
Viator
The journey continues through Chicago's underground Pedway tunnels, then reemerges at the street level to revel in City Hall's breathtaking design.
Viator

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Then, as you stroll along the Chicago Riverwalk, you'll admire classic buildings like the "corncobs" (aka the Marina Towers) and the Willis Tower (which many locals still refer to as the Sears Tower).
Viator
Other stops along the tour have included The Bean (ie Cloud Gate), Macy's (formerly Marshall Field's), the Palmer House hotel, and more.
Viator
Of course, no trip to Chicago would be complete without sampling its fabulous fare. Restaurants big and small offer up their best dishes — like Italian beef, Chicago-style hot dogs, deep-dish pizza, and two other beloved snack spots.
Viator
And if you really want to impress your guide, memorize the seven "Chicago-style" dog dressings: mustard, neon green relish, chopped onion, celery salt, tomato, a pickle spear, and sport peppers.
Viator

So, would you spend a day having an urban adventure with the best walking tour in Chicago? Where’s a place in Illinois you’ve always wanted to tour? Tell us in the comments! Start planning your visit now by booking your excursion with Viator — and you may want to plan sooner rather than later, as this top-rated tour has been known to sell out! Or, if you want to just focus on one area of Chicago, this architecture boat tour through the Chicago River is a favorite for half the price. While you’re here, make it a weekend getaway! A room at The Langham in River North is a luxurious experience with amazing city views, or a night in The Godfrey Hotel offers a fantastic rooftop bar and sleek rooms with an unbeatable location for a fraction of the price.

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