Wendella Boat Tour. Photo by Lou Stejskal via Flickr

Top Chicago Architecture Tours

Chicago Architecture Center River Cruise

This should be a prerequisite to calling yourself a Chicagoan. Board the boat near the Chicago Architecture Center and travel west and south along the Chicago River to see over 50 of the city's greatest buildings. The 90-minute tour is offered in four languages and many times throughout the day most days.

Be sure to visit the Chicago Architecture Center afterward to learn more about the history and biographies of the city's greatest designers and builders.

Wendella 90-minute Chicago River Architecture Tour

Like the Chicago Architecture Center tour, these boat rides give guests a glimpse into the past 130 years of Chicago's history. You can also enjoy beverages and snacks at Wendella's on board.

Free Tours By Foot

Boat tours are amazing, but the cost can add up quickly, especially for families with more than one or two kids. Free Tours By Foot offers walking tours showcasing the architecture of downtown, Lincoln Park, the Magnificent Mile, and more at pay-what-you-can prices.

Tours are available Wednesday through Monday and approximate times and walking distances are posted for each tour. Make a reservation in advance to ensure you get the tour you want.

Inside Chicago Tours

We all know what the exteriors of Chicago's great buildings look like, but what about the interiors? There are amazing gems of artwork in building lobbies, atriums, elevators, and even in L Stations and along the Pedway. Join a local expert to find all the great bits of interior architecture the Windy City has to offer.

 
Photo courtesy of Bobby's Bike Hike

Best Chicago Food Tours

Bobby's Bike Hike

By bike or by food, find some of Chicago's favorite foods on these tours. Choose from a family-specific tour, or tours for all ages that focus on Chinatown or holiday-centered fare. Grown-ups can also choose tours like the Chicago Specialty Foods Tour or the West Side Food and Bike Tour, which include beer and wine. 

These are a great way to combine knowledge of the city's attractions with tasty treats like Italian beef, hot dogs, and more. 

Pizza City USA

Are you a deep dish or a tavern-style family? Either way, you might love the bus or walking tours from Pizza City USA. Bring an empty stomach: you'll get four pizza samples in a general city-wide bus tour or walking tours of Bucktown/Wicker Park, the West Loop, or downtown. Grown-ups can also buy beer at each site with a valid ID.

Chicago Underground Donut Tour

Part food tour and part history lesson, this walking tour of downtown and River North is as sweet as it gets! Try samples from four different donut shops, including Doughnut Vault and Do Right Donuts, and learn about the Chicago River, the central business district, and the Magnificent Mile with anecdotes from a local expert.

Best Chicago Ghost and Cemetery Tours

Graceland Cemetery Tour

Do you ever wonder why the cemetery at Clark and Irving Park is so big and who is buried there? Spoiler alert! Many of Chicago's founding fathers are here: Daniel Burnham, Potter Palmer, Charles Wacker, and George Pullman; Chicago's neighborhoods, streets, and parks are named in their honor and you'll learn all about them on this unique Chicago tour.

American Ghost Walks

Many Chicago ghost stories are expanded upon in the wide variety of tours offered by American Ghost Walks. Choose a general ghost tour covering a larger portion of the Chicago area, or pick a specific ghost story you want to learn more about. We're excited for our kids to be big enough for The Devil in the White City tour, and there's also a walk featuring Resurrection Mary.

As a bonus, ghost hunts happen in different suburbs and neighborhoods like Lincoln Park, River North, Woodstock, Aurora, and Naperville!

Windy City Ghosts

Choose from the Hauntings of Chicago tour or the Chicago Gangsters and Mobsters walking tour for a few thrills and chills. The tours travel across burial grounds, haunted hospitals, and pubs that survived the prohibition. Much of the tours take place in Lincoln Park, where even the most seasoned Chicagoans may hear a new ghost story or two. 

 
The Vivian Maier mural was painted by Eduardo Kobra in Bucktown. Photo by Jay Galvin via Flickr

Chicago Art Tours 

Offbeat Street Art Tour 

We all love the Art Institute and the Museum of Contemporary Art, but there are also cool paintings on the streets of Chicago that are free for all to enjoy. The Offbeat Street Art Tour. takes visitors on a two-mile, two-hour journey through the Bucktown, Wicker Park, and Logan Square neighborhoods to explore cool, funky, and unique pieces on walls and in alleyways.

Another cool part of this tour is that it can change as new murals pop up or old ones disappear.

Chicago History Museum Mural Tours

Old Town's Chicago History Museum changes up its tours regularly, but the Pilsen Mural Tour and the Hyde Park Mural Tour are frequently in the mix. The Pilsen tour meets at the National Museum of Mexican Art; it's a 1.5 to 2-hour loop of public art on railroad viaducts, buildings, and doors showcasing the evolution of the city's Latin American heritage. The Hyde Park tour mostly consists of artwork in the Metra underpasses between Hyde Park Boulevard and Cornell Avenue, many of which were painted in the 1970s.

Walk Chicago Tours Public Art in the Loop

Many Chicagoans can already identify the Picasso, Chagall, and Miro statues in downtown Chicago; this tour gives a more expansive view of some of the more than 100 pieces of art on display throughout the Loop.

Listen to the stories of these Chicago treasures, and maybe you'll find out why there's a flamingo in a temperate climate or what that black-and-white thing outside the Thompson Center is anyway.

Chicago Tours with Unique Forms of Transporation

Big Bus Tours Chicago

Get on a hop-on hop-off tour during the day or take a sunset tour in the evening on this double-decker bus that travels throughout Chicago's downtown. See the Sears (Willis) Tower, Millennium Park, the Art Institute, Water Tower, Navy Pier, the Adler Planetarium, and more throughout your day-long journey. Start and stop at any point along the trip.

Chicago Segway Tours

Some parents remember how cool Segways seemed in the early 2000s, and they make the perfect alternative to kids complaining about tired feet on a walking tour today. Chicago Segway Tours offers regular Museum Campus and Lakefront tours, or you can take a nighttime tour to see the fireworks on Navy Pier. Larger groups can book a specialty tour based on their time availability.

Urban Kayaks Chicago River Tour

Tandem kayak with your kid on an intro paddle or a history tour along the Chicago River. The intro paddle includes one hour on the water and is kept to small sizes of one instructor per six boats. The more advanced tour involves a two-hour paddle in the river and teaches tourists about architecture and history. Lakefront and fireworks tours are also available, but may be better for teens and up.

All Flickr photos in this post are licensed with CC BY-NC-ND 2.0.