The 6 best tours and walks in Chicago

If you look for flexibility when it comes to sightseeing, this bus tour is your best bet. Choose between a 24 or 48-hour ticket and alight as you please; stepping on for a relaxing ride around the city, and stepping off when you'd like to get up-close and personal with one of the landmarks or attractions. You'll be passing by Willis Tower, Adler Planetarium, Chicago Water Tower, Magnificent Mile and many more must-see sites – with plenty of conveniently-located stops along the way. The route is a loop, so you won't have to worry about straying too far from the starting point. 

Don't miss: A shopping trip at Magnificent Mile or a food pitstop at Navy Pier (or both). 

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.

Dont miss: Drinks from the on-board bar (don't forget to bring cash). 

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 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. 

Don't miss: The chance to marvel at Hugh Hefner's original Playboy Mansion. 

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. Reservations are required.

Don't miss: You'll get to see bits of where Dark Knight was filmed, which will suit the batman fans among you. 

No Chicago tour will take you higher than the Chicago Helicopter Experience, which offers aerial views 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. 

Don't miss: A lesson in Chicago's rich architecture and architect Frank Lloyd Wright. 

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, 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.

Don't miss: The chance to ask your guide for some top dinner recommendations.