The Best of Chicago’s Walking Tours

Chicago has been named among the top walkable cities in America by several top travel publications. With being named a top walkable city comes the reputation of having entertaining walking tours through Chicago that explore the unique cultures, neighborhoods, and history year-round. The city’s many festivals and events of music, comedy, sports, and food are easily accessible by foot from the spring to the fall and are a highlight on many of the best Chicago walking tours. During the winter months, visitors and locals can still enjoy strolling along on a guided walking tour that visits Chicago’s museums and its classic culinary scene.

To provide our readers with fun ideas on exploring the beautiful, flat Windy City on foot we have put together a list of the best Chicago walking tours for you to enjoy throughout the seasons in Chicago. The best of Chicago walking tours include sightseeing of local neighborhoods and popular attractions, informative historical tours, samples of classic Chicago foods and drinks, and guided walks of Chicago’s unique architecture.

Chinatown Food & Culture Walking Tour

Chinatown Chicago

If you love learning about and immersing yourself in various cultures, then Bobby’s Bike Hike’s Chinatown Food & Culture Walking Tour is the right walking tour for you. Bobby’s Bike Hikes has been voted the number one walking tour company in all of Chicago and offers numerous other walking tours, along with food and bike tours.

Chinatown is a lively neighborhood located near Chicago’s south loop neighborhood. The neighborhood is perfect for Chicago sightseeing and allows visitors and locals alike to immersive themselves in food, shopping, and musical experiences outside of the downtown area. 

With endless options available, it can be overwhelming for visitors to decide which places to visit for the whole Chinatown experience. This cultural walking tour provides the perfect overview for those interested in experiencing all of Chinatown’s best aspects. The tour offers a unique opportunity to learn about Chinese history and immigration specific to Chicago’s Chinatown, along with historic information you might miss in a self-guided tour. mongolian hot pot dish on Chicago Chinatown food tour

A city tour of Chinatown would not be complete without checking out Wentworth Avenue, located at the heart of Chinatown. This area features some of the best shopping in all of Chinatown.

This tour covers 1 mile in roughly 2.5 hours, is very easy walking for most people, and has ADA accessibility. Some unique aspects of the Bobby’s Bike Hike’s Chinatown Food & Culture Walking Tour are sampling popular dishes such as Dim Sum, Mongolian Hot Pot, and more obscure foods such as food derived from a northwestern city in Xi’an. We love to feed our guests ;). The ticket price also includes all food samples! You can upgrade to the VIP package if you want to try delicious samples of bubble tea, beers, and plum wine.

With all the sightseeing, local history, authentic dishes to sample and shopping, this is easily one of the best Chicago walking tours. This tour offers a one-of-a-kind experience for Chicago visitors, and even local Chicagoans wanting to learn about the charming Chinatown neighborhood and experience first-hand the cultural dishes and traditions. 


Chicago Loop Walking Tour

Famously referred to as the downtown of Chicago, the Loop neighborhood has endless Chicago sightseeing and breathtaking views. Step into the business district of Chicago with this informative walking tour offered by Wild Onion Walks Chicago.

Visitors will get to visit Chicago staples such as the elevated “L” train, the Willis Tower, and Chicago Cultural Center. This tour by foot is also great for individuals interested in learning about the Loop’s quieter and lesser-known areas (they deserve some attention too!). The Loop neighborhood is filled with a rich history that most people might not learn in a self-guided tour. This tour’s guide is committed to educating customers on all the exciting details behind Chicago’s rich cultural history.  

This tour is about two hours long and is not wheelchair accessible. This city tour is not recommended for individuals with mobility issues.

Chicago Favorites Walking & Food Tour

group on Chicago walking tour in the Loop Neighborhood

Bobby’s Bike Hike’s Chicago Favorites Walking & Food Tour is perfect for individuals who want to check out the best of Chicago sightseeing and food all in one day. This exciting tour lets you get a taste of the Windy City’s staple food items such as deep-dish pizza and the one-of-a-kind “Chicago-style “hot dog.

Chicago-style Hot Dog on Food Tour of the City with Bobby's Bike Hike


Visitors can find it challenging to plan out their visit to this beautiful city. Bobby’s Bike Hike’s Chicago Favorites Walking & Food Tour has organized the perfect tour for such individuals. It might be challenging to get such a classic “Chicago” experience on another tour or a self-guided tour. For all the foodies reading this, you’ll want to check out our blog on the Best Chicago Food Tours that incorporates either walking or biking to indulge in the city’s classic tastes. 

Visitors will gain valuable information and history of all of the beloved landmarks they visit. They will also learn the stories behind how Chicago’s staple dishes and establishments were created. The energetic and entertaining tour guide will take visitors to classic Chicago restaurants such as Giordano’s deep dish, Millennium Dogs, and Italian beef to die for.

deep dish chicago classic pizza slice being picked up

This tour takes guests along Chicago’s most beloved locations, such as Millennium Park. Guests love to take pictures for their Instagram by posing next to staples such as the Cloud Gate (famously referred to as “the Bean”). The tour also appreciates Chicago’s breathtaking skyline by stopping in the heart of Chicago’s river walk. Truly, Bobby’s Bike Hike’s Chicago Favorites Walking & Food Tour is one of the best tours by foot available in the Windy City. 

The tour lasts around 2.5 – 3 hours and is 1.4 miles long. It is easily walkable for most people. The tour is also ADA accessible. The ticket price includes all food samples. Beer lovers can upgrade to the VIP package to sample three delicious local craft beers.


Chicago Ghost Tours & Pub Crawls

Chicago’s Lincoln Park neighborhood has a spooky history of haunted spirits and murders. Nightly Spirits Chicago Ghost Tours & Pub Crawls is the perfect tour for those that want to get a little creeped out. The tour takes you along Chicago’s most haunted alleys, pubs, and buildings. A glass of wine can help take the edge off if visitors get too scared ;). This ghost tour includes unique features you will not find in other ghost tours or on a self-guided tour. The energetic tour guide will tell you all the stories about murdered gangsters and spirits that still haunt the buildings they used to own. 

The tour covers one mile of walking distance, lasts about two hours, and is easily walkable. You must be over 21 years old to purchase tickets. However, purchasing liquor is not a requirement inside the pub. The cost of liquor is not included in the ticket price. Whether it’s Halloween time or not, this is one of the spookiest and best walking tours available in Chicago.  

Holiday Hike Chicago-Style—  Festive Holiday Food & Walking Tour

guided walking tour to holiday markets in Chicago

There is nothing quite like Chicago during the festive holiday season. Experience the magic for yourself as the city lights up with beautiful lights and lively Christmas decorations in every corner. Bobby’s Bike Hike has created one of the best Chicago neighborhood walking tours for those in the holiday spirit. The Holiday Hike Chicago-Style: Festive Holiday Food & Walking Tour takes guests to unique holiday activities one can only experience while in the Windy City. Visitors will witness State Street’s breathtaking holiday decorations, the European-inspired Christkindlmarket, and the impressive Christmas tree at Millennium Park. Guests will enjoy the holiday festivities with a guide to lead them to the best markets, eateries and share holiday-themed city facts. 

This holiday walking tour lasts about 3 hours, is easily walkable for all ages, and accommodates people with disabilities. The ticket price includes delicious holiday treats and food samples, and the beer fanatics can enjoy seasonal craft beer tastings on the tour. Individuals looking for a holiday-themed city walking tour must check out this entertaining and festive tour.


We Love Chicago Walking Tour

Group on Walking Tour at Chicago Cloud Gate

Chicago has so many hallmark features. Some landmarks are famous worldwide while others are hidden gems. See It All Chicago has organized a walking tour that takes customers for a stroll through Chicago’s most beloved features. This tour exposes you to Chicago’s unique architecture in a way that other tours or a self-guided tour won’t be able to. Visitors will check out Chicago’s very first skyscrapers; stopping by famous Chicago buildings such as the Marquette Building, the Rookery Building, and the Chicago Board of Trade Building. Art fanatics will also appreciate this walking tour because they will see masterpieces by famous artists such as Picasso.  

The We Love Chicago walking tour is a little under two miles and lasts about two hours. The path is easily walkable and wheelchair accessible. The tour guide also educates the visitors on the exciting history behind all the adventures they will be embarking on. If Chicago’s beautiful architecture and art fascinate you then this is one of the best Chicago walking tours for you. You can also learn more about Chicago architecture by reading our blog on the 10 Famous Chicago Buildings and Architecture You Need to See.

Chicago’s active downtown, diverse neighborhoods, and urban lake beaches make it a popular destination for travelers and locals to explore, both by foot and on the city’s robust public transit. The city’s pedestrian walking trails and bike routes along the river and lakefront offer breathtaking urban views and access to explore one end of the city to the other.

There are numerous walking routes one can take to explore the city on their own at their own pace, but a guided Chicago walking tour gives more depth, organization and insight into the experience. Bobby’s Bike Hike provides a number of the best walking tours in Chicago, from the Chinatown Food & Culture Walking Tour to the Chicago Favorites Walking & Food Tour.

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2021-05-11T14:52:59-07:00March 3rd, 2021|0 Comments

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