So, you want to explore the Windy City? You’ve come to the right place. Chicago is home to many must-do sightseeing attractions and tours, from walks along the waterfront to boat rides down the Chicago River, all while eyeing up its iconic skyline.
Chicago tours are next to none (and yes, there is one to sample its famous deep-dish pizza). So, it’s time to grab an eyeful (and mouthful) of what Chicago tour attractions have to offer.
Chicago Architecture Boat Tour
What better way to discover more about the city’s iconic architecture than by cruising along the Chicago River, with a history lesson on the side? The city has a number of boat tours led by architecture experts and city guides to give you an insight into what really went into building Chicago. See the whimsical Marina City towers, the super-tall Willis Tower and the Spanish-influenced Wrigley Building.
Browse deals on Chicago boat tours.
Big Bus Tours
Ok, so maybe you don’t fancy getting your feet wet. How about doing the classic tourist thing and jumping onto a Big Bus Tour? This way, you’ve got the freedom to hop on and off whenever and wherever you like, as well as exploring the city at night. This Chicago tour is perfect for first-timers to the city, with stops at Millennium Park, the Hancock Center & Observatory, Buckingham Fountain and much more.
Explore the Big Bus Tour deals.
City Cruises
Set sail on a Premier Chicago Cruise for an unforgettable dining experience on Lake Michigan, featuring gourmet meals, creative cocktails, live DJ entertainment, and breathtaking skyline views.
See our Chicago City Cruises experience deal.
Aerial Tour
Want to keep your feet dry, get up high, and see Chicago from the sky? Consider a skyline aerial tour! It’s obviously not for those with an aversion to heights or who like to keep their feet on the ground, but an aerial tour is the best way to see literally all of the city in one go.
Explore all Chicago flight tour deals and offers.
Historical Crime Tour
Chicago is famous for hot dogs, deep-dish pizza and some of history’s most infamous mobsters. To get a taste of that last part, take a Chicago Crime double-decker bus tour on a historical journey through the city’s dark corners, hidden mysteries and blood-soaked mob-ridden legacy, from Capone to Dillinger. It goes without saying, this one’s not for kids.
Check out the Chicago Crime Bus Tour deals – from $70.
Underground Donut Tour
Do we really need to say more than the words “underground donut tour” (other than “donuts included in the ticket price”)? This unique Chicago sightseeing tour takes you through a handpicked selection of the city’s best and hidden donut shops, sampling tasty treats as you go. Tour guides will also accommodate any dietary requirements so it’s suitable for everyone!
Check out the Underground Donut Tour deal at Groupon.
Chicago Food Walk
Worried you’ll get bored of donuts? We don’t think that’s possible but, just in case, you could also venture out on the famous Chicago Food Walk instead (or as well!). You’ll explore and sample food from some of the town’s most-iconic grub spots, including stuffed sandwiches, hot dogs and, of course, pizza. We think it’s worth the ticket price simply because you probably won’t have to eat again for the next five days.
Take a look at the Chicago Food and Culture Walking Tour - from $39
Pizza Tour
Pizza time! The food tour of dreams — the Chicago Pizza Tour — takes you on a greasy, cheesy journey through the city, stopping at a selection of amazing restaurants for a slice or two. Plus, you don’t even have to walk around all full of mozzarella and marinara — this is Chicago’s only bus-guided pizza tour.