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. Reservations are strongly recommended. $47–$52
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 along the Lakefront Trail, admiring the breathtaking skyline sights. Ticket price includes bike, helmet and guide. $46.30
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—and for a total steal. $48
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). Guests share iPads loaded with historic photos, videos and archival maps for additional context. Reservations are required. $23
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. $158
Want to take in a history lesson over a pint of beer? This walking tour offers a behind-the-scenes look at three of the city's oldest and most influential watering holes. Along the way, you'll learn about the legendary mobsters, 1960s nightlife and so much more. Complimentary appetizers are served at each bar, but guests should bring cash for 2.5 servings of beer, wine, soda or water. $38
A visit to the Chicagoland area wouldn't be complete without a tour of the Frank Lloyd Wright Historic District in Oak Park, home to the world's largest collection of Wright-designed buildings, including the architect's own home and studio. You can take a self-guided walking tour, but for the full experience you'll want to spring for the Wright Around Oak Park tour, a three-hour walk that includes access to Wright's studio as well as visits to nine other buildings. $60
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, handmade chocolates and more. Consider it your primer to Chicago's most notable food groups. $55
Chicago has been the backdrop to many classic films and Hollywood blockbusters—from Ferris Bueller's Day Off to The Fugitive to The Dark Knight. This bus tour ventures all over the city to more than 30 locations where more than 80 movies were shot. You'll learn behind-the-scenes trivia, details of current filming activity in Chicago and more. It's a reel adventure. $30
Just a heads up: This is not a tour for visitors to Chicago who want to "blend in" and "do what the locals do." Riding a Segway around the Loop with your friends and family is akin to tattooing "TOURIST" on your forehead. If you don't mind looking like a mall cop, it's way more fun than walking. You'll explore city landmarks, famous architecture and scenic spots along Lake Michigan. $70.85
If flying buttresses, Tiffany mosaics and Gothic columns get you all hot and bothered, you’ll love these fascinating architecture tours of Chicago
For a family vacation that’s as educational as it is entertaining, you’re going to want to book some kid-friendly tours in Chicago
Explore Chicago's amazing architecture from the top of a boat.
Learn how your favorite beer is brewed while sipping a pint on these behind-the-scenes tours.
Soar over the skyline on these high-flying excursions.
There's no more efficient (and fun!) way to experience the best Chicago's restaurants than on a food tour.