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Shoreline Architectural Boat Tour
Photograph: Roark Johnson

The 6 best tours and walks in Chicago

Experience the city's rich history, culture, architecture and attractions on these essential Chicago tours

Written by
Kris Vire
Morgan Olsen
Rhys Thomas
Alex Floyd-Douglass

There are many ways to experience Chicago: by foot, bike, boat, bus, trolley, kayak… So in an effort to keep you on the right path while you're exploring the city, we've rounded up some top-rated Chicago bike tours, walking tours, boat tours and more. These are, in our opinion, the best ways to discover Chicago's best attractions, beautiful buildings, history and culture (not to mention the best restaurants, craft breweries and the lakefront). Embrace your inner tourist and hit the road on one of these adventures. Keep a couple dollars in the pocket though, there's a whole lot of food and drink to be added on to your adventures. 

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Chicago Architecture Foundation River Cruise

1. Chicago Architecture Foundation River Cruise

This Chicago architecture tour is a must for entertaining family and friends from out of town or just orienting yourself to the city’s many architectural wonders. With a knowledgeable docent in tow, you'll cruise along the Chicago River from River City north to Goose Island, taking in stunning, unimpeded views of some of the city's most famous skyscrapers along the way. On the river, you'll take in over 40 landmark buildings, including towers from the Tribune to the Trump. There's a bar too, just in case. Reservations are strongly recommended.

Lakefront Neighborhoods Tour

2. Lakefront Neighborhoods Tour

If you need a crash course in why Chicago is so damn awesome, this bike tour of the Lakefront should do the trick. Within three hours, you'll see Gold Coast mansions, Lincoln Park Zoo, the old Playboy Mansion and North Avenue Beach. You'll bike approximately seven miles (easy going in three hours) along the Lakefront Trail, admiring the breathtaking skyline sights. You'll also get a little glimpse at Oprah's pad, and of course, the whole affair will enrich both your mind and body. A lovely way to spend a day. Ticket price includes bike, helmet and guide. 

Chicago Grand Half-Day Tour

3. Chicago Grand Half-Day Tour

If you've got time to spare, dive into this immersive half-day tour of the city. You'll see the North and South sides, check out some of Chicago's most beautiful parks, snap a photo at the Adler Planetarium and take in some of the most inspiring architecture around town. The four-hour excursion might just be the best way to see it all. There's a choice of morning or afternoon tours too, so you can check out the windy city whenever it suits your schedule. Oh, and it's a bit of a steal.

Chicago Pedway Walking Tour
Photograph: CC/Flickr/John Greenfield

4. Chicago Pedway Walking Tour

After you've gotten an overview from the river, get inside some of those buildings with this 90-minute walking tour. Making use of the Pedway, the tour is almost completely indoors, making it a good option for winter visitors (or stormy summer days, equally common). Guests share iPads loaded with historic photos, videos and archival maps for additional context. The guides are known to be a witty bunch too, so it's a good time all round. You'll also get to see bits of where Dark Knight was filmed, which will suit the batman fans among you. Reservations are required.

Chicago Helicopter Experience

5. Chicago Helicopter Experience

No Chicago tour will take you higher than the Chicago Helicopter Experience, which offers aerial tours of the city's skyline. You'll board a chopper on the outskirts of Bridgeport and fly up the coast of Lake Michigan to Montrose Harbor and back in about 15 minutes. The cost of the flight might seem a little steep, but the photo opportunities are priceless. When else have you seen such a tall city, a wonderful lake, and so much more from a birds-eye view, ever? Exactly. It's a doors-open experience too, to get the adrenaline pumping. Time to get to the choppa!

Chicago Style Food Tour
Photograph: Nick Murway

6. Chicago Style Food Tour

If you want to fill up on iconic Chicago foods while you're in town, look no further than this epic three-hour guided adventure. Though the stops change occasionally, expect to nosh on deep-dish pizza (a pie, really, cheesy stodge factor 100), Chicago-style hot dogs (poppy seeds galore), handmade chocolates and so much more. Have a light breakfast, is our advice. Consider it your primer to Chicago's most notable food groups. The number of people per tour is pretty small too, so you can really geek out when asking the questions.

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