Chicago City Tours

Explore Chicago Tours by Land & Sea

Chicago tours will widen your knowledge about the city and allow you to experience the rich history, cultures, and enjoy the beautiful view of this city. No matter what time of the year it is, Chicago always has something for you to see and do.

Whether it’s spring, summer, winter or fall, taking one of the many Chicago tours available can allow you to see this city during it’s many seasons. Venturing out in the spring when the flowers and greenery are coming alive, and in the summer when everyone is enjoying the weather, and outdoor fun can be an amazing way to spend time. If the seasons don’t limit you, you can continue touring the city in the fall when all the bright colors are at their peak, or in the winter when the outdoor can appear like a winter wonderland.

There are many ways to explore this city. Whether it’s by bus, horse drawn carriages , or walking. There are a variety of themed tours that you can adventure out on and learn more about Chicago.

Trolley tours are another option and one of the more popular tours in the city. You can ride around in a red trolley and get a first hand view of what Chicago has to offer while enjoying the fun that only a trolley can bring. If you are a hands on person who wants to take your voyage into your own hands you can discover the city via a Bike or a Segway tour. Some tours occur during the day and night. This can give a person a chance to see the city’s contrasting views.

Chicago Neighborhood Tours

Sample the charms and histories of three diverse neighborhoods. From the Greek Town, Chinatown & Little Italy tour to the new Chicago Public Art tours, Summertime Sampler tours are the perfect introduction to Chicago communities.  Encounter the history, culture, and people of 35-plus Chicago neighborhoods on 15 different tours. Church spires and stylish boutiques define Wicker Park & Ukrainian Village. Uncover Chicago’s past and last Masonic Temple when Jefferson Park, Portage Park & Six Corners debuts. On the new South Chicago tour, think “Green” at Calumet Park and the old U.S. Steel site. Rotating on Saturdays, Neighborhood Tours hold surprising discoveries.

With many different tours to choose from, the Chicago Neighborhood Tours offers something for every section of Chicago. You can choose to do a single neighborhood tour such as Bronzeville or Devon Avenue – or try a Summertime Sampler, which will take you on a tour of several Chicago neighborhoods in one afternoon, such as Greek Town, Chinatown & Little Italy. Most tours begin at 10 am on their respective dates. Mine the city’s hidden gems, its neighborhoods. From South Side neighborhood Beverly on the new Beautiful Beverly tour to historic parks on the new Garfield Park & Beyond tour, Neighborhood Tours showcase the arts, culture, history, and people of Chicago.

Get in on memorable events, people and ideas that helped make up modern Chicago on 6 different expert-led tours. On The White City tour, feel the excitement of the 1893 World’s Fair, or delve into the history of Greek Chicago. Navigate Polish Chicago, the largest such community outside Warsaw, and try a tasty assortment of ethnic cuisines on Taste of the Neighborhoods.

Summertime Chicago Tour

Sample the charms of diverse neighborhoods on 4 abridged tours. The delightful trios featured include the popular Greek Town, Chinatown & Little Italy and brand-new, Bucktown, Humboldt Park & Logan Square. In several communities on Art Around Town, see classic, contemporary, indoor and outdoor mosaics and sculptures. Summertime Sampler Tours
are the perfect introduction to Chicago’s many neighborhoods.

Albany Park

More Albany Parkers were born around the globe than any other Chicago community’s residents. Begin in this sprawling neighborhood visiting local treasure Indian Boundary Park before enjoying light refreshments at Superdawg Drive-In. Travel its “Bungalow Belt”, spot urban wildlife roaming the 155-acre North Park Village (once the Municipal Tuberculosis Sanitarium site) and leisurely walk North Park University campus, along the river. End at the serene Cambodian American Heritage Museum.



Art Around Town

Amazing, world-class artworks add panache to Chicago neighborhoods with hundreds of sculptures, paintings, murals and monuments from private and public enterprises as well as Chicago’s Public Art Collection.  Spot pieces in and around building lobbies, parks, plazas, viaducts and other surprising places.  The intimate knowledge gained illuminates why Chicago takes pride in being a leading promoter of public art.

Beautiful Beverly

Trees galore, historic homes—including the country’s largest cache of architect Walter Burley Griffin designs—beautiful parks and lovely churches distinguish Beverly Hills. And winding streets wow at every turn. Join a discussion at the Ingersoll-Blackwelder House, a privately owned historic residence. Delight in refreshments at a local restaurant in Beverly’s charming shopping district. Drop by Beverly Arts Center for a look at its current exhibits and performance schedule.


Bucktown, Humboldt Park & Logan Square

Take in the 200-plus-acre Humboldt Park‘s Refectory and Boat Landing, Rose Garden, and Receptory and Stable, designed by turn-of-the-20th-century greats such as landscape architect Jens Jensen. Nearby, Logan Square offers some of the city’s most elaborate dwellings, facing Logan Boulevard, and the striking Illinois Centennial Monument, commemorating the 100th anniversary of Illinois’ 1918 statehood. In Bucktown, look around dozens of shops on Damen and Armitage avenues.

Chicago’s Magnificent Churches  

Observe a captivating cross-section of religions, cultures and communities when you call on three or four Chicago-area churches, temples and sanctuaries.** Compare and contrast religious faiths and customs on this popular tour of Chicago’s sacred spaces. Restaurant stops will vary by community areas visited. ** Church stops vary by tour date and are subject to availability

Devon Avenue

Cruise through the Bryn Mawr Avenue [national] Historic District before reaching Devon. Set off on foot for guided discovery. Find exotic delicacies in international delis and grocers. Browse sparkling jewelry stores and colorful sari shops, and sample Indian tasty treats along the way. Come across Devon Avenue’s Jewish roots to the east and later, its Croatian legacy during a short discussion at Angel Guardian Croatian Catholic Church (subject to availability).



Greek Chicago

On this excursion, community experts herald the fascinating history, customs, and religion of Greek Chicagoans. The importance of the famed Jane Addams Hull House to early Greek immigrants comes to light during a private tour and discussion. Then, the National Hellenic Museum chronicles their American experience. Savor lunch at a Greek restaurant before visiting Annunciation Greek Orthodox Cathedral** for an in-depth look at the Greek Orthodox religion.

storefront on devon avenue

Great Cemeteries of Chicago  

Arrive at the city’s most famous resting place, Graceland Cemetery, for a unique twist on defining moments and key players. View the eye-catching architecture and art honoring Chicago leaders, politicians and everyday citizens including architects Louis Sullivan and Daniel Burnham, retailer Marshall Field and hotelier Potter Palmer. At Rosehill’s vast Mausoleum, unearth little-known accounts, peer through awe-inspiring Tiffany windows and find opulent tombs of notable families. Wear comfy shoes.

Garfield Park

Greek Town, Chinatown & Little Italy

Look into the Near West Side neighborhoods of Greek Town and Little Italy where Greeks and Italians first settled. Traverse Little Italy’s Taylor Street, as have generations of Italian families. Enjoy vibrant Chinatown of the Near South Side. Browse Chinatown Square and dozens of shops full of all kinds of goods from China and other Asian locales. Spend some time on your own exploring Little Italy and Chinatown.

Historic Bronzeville

A leading 20th-century African American community, Bronzeville is moving toward a modern-day revitalization. Travel throughout this quiet neighborhood, and tap into past and present at DuSable Museum of African American History, a major independent institution. Observe youths and adults in action at Little Black Pearl Art and Design Center, offering opportunities through cultural entrepreneurship. Finish up at one of the lovely area galleries, Gallery Guichard.

storefront on devon avenue

Hyde Park & Kenwood

Here’s where lakefront vistas, architecture, ancient history and Nobel Prizes meet. Admire Kenwood dwellings including President Barack Obama’s. Enter Hyde Park’s Art Deco–style St. Thomas the Apostle Catholic Church,** by noted architect Barry Byrne. On the University of Chicago campus, enjoy the world-famous Oriental Institute Museum’s Egyptian, Iraqi and Persian antiquities, and Rockefeller Memorial Chapel.** At tour’s end, stroll the enchanting, lakeside Osaka Garden on Jackson Park’s Wooded Island.

Hyde Park

Humboldt Park, Wicker Park & Ukrainian Village

Discover the unique histories, traditions, and stories of these three neighborhoods. See the distinct homes, churches, and parks in each. Gather in the heart of Wicker Park for self-exploration.

Irish Chicago

Irish Chicago’s vital role, during early American history and since, comes alive at Holy Name Cathedral,** the seat of Chicago’s Roman Catholic Church. Tour the second oldest church, Holy Family** (a survivor of the Great Chicago Fire). The traditionally Irish Bridgeport neighborhood provides the backdrop for exploring why Irish immigrants settled here. Following lunch at a local Irish pub, check out the lively Irish American Heritage Center.

Jefferson Park, Portage Park & Six Corners

Both Jefferson Park and Portage Park’s peaceful residential streets surround busy far-north hubs such as Six Corners. At Portage Theater, discuss its restoration, 1920s beaux-arts interiors, and audiences then and now. Look into spiritual and architectural matters at the Spanish Revival–style Our Lady of Victory Church.** Go behind the scenes at Gateway Theater, serving Jefferson Park’s thriving Polish population alongside others, and Jefferson Park Masonic Temple.

Hyde Park

Land of Lincoln

Lincoln statue in Senn Park marks an 1860 presidential campaign stop. Enjoy The Chicago Lincoln in Lincoln Square and Lincoln Restaurant’s light fare. It’s a friendly talk on the Lincoln-Douglas Debates at Stephen A. Douglas Tomb and Monument. View Lincoln, The Orator near Oak Woods Cemetery Civil War graves. In Lincoln Park, stand in awe of the Standing Lincoln and Chicago History Museum Lincoln memorabilia.

Little Italy

Little Italy

Late 1800s Southern Italians and Sicilians settled this Near West Side jewel, then hosting Chicago’s largest Italian population. Muse on early Italian heritage during the private tour-discussion at national landmark Jane Addams Hull-House Museum. Hit Taylor Street for refreshments at a local Italian restaurant before a guided walk through the neighborhood’s quiet, tree-lined streets. Finish with a short talk at the Shrine of Our Lady of Pompeii.** Bellissimo!

Little Italy, Pilsen & Little Village

Sample Little Italy, the charming home to generations of Italians. Hear about Pilsen’s Bohemian roots and modern-day Mexican and Mexican American community, shared with nearby Little Village. Browse Little Village’s 26th Street shopping district on your own.

Little Italy

Pilsen & Little Village

Viva, Pilsen and Little Village! Together, they’re one of the country’s largest Mexican and Mexican American communities. Scope out Little Village’s 26th Street. This top-shopping destination offers many diverse establishments including authentic dulcerías (sweet shops), restaurants and panaderías (bakeries). In Pilsen, visit a local church** and view several bold, expressive murals and mosaics en route to the nation’s largest and accredited Latino museum, the National Museum of Mexican Art.

Pilsen & Little Village

Polish Chicago

Where’s the largest Polish population outside of Warsaw, Poland? Chicago! Experience it starting with St. John Cantius Catholic Church,** whose spectacular Romanesque Baroque architecture makes it a standout. As you veer along Milwaukee Avenue the “Polish Triangle” is revealed. Break for lunch before the enjoyable guided tour and discussion at the Polish Museum of America. There’s ample time to roam on your own through this important cultural institution.

Pullman Historic District

Pullman Historic District—the first planned industrial town, created by George M. Pullman of Pullman Palace Car Company—is a city, state and national historic landmark. Architect Solon Beman designed this 1896 World’s Most Perfect Town. The exploration is afoot with a short historical presentation inside the Pullman Visitor Center. On a comprehensive walking tour, visit Greenstone Church** and the celebrated Hotel Florence for a restoration update and tour.


South Shore Neighborhoods

After the 1893 World’s Columbian Exposition, South Shore became a middle-class sensation. Alive with such cultural, historical and architectural landmarks as the intriguing South Shore Cultural Center, South Shore, Chatham and Greater Grand Crossing offer much. Visit Saint Philip Neri Catholic Church,** and spy the restored New Regal Theater. Expect more pleasurable viewing at the award-winning Gary Comer Youth Center, whose John Ronan Architect design supports local kids’ activities.

South Shore Neighborhoods

South Chicago

Long-standing industrial pockets on the far-south shore, South Chicago and Southeast Chicago are “going green”. Take stock of the old U.S. Steel South Works site slated for reuse in a LEED-certified eco-friendly community. Visit Saint Michael the Archangel Catholic Church** founded for Polish immigrants, whose later arrivals for steel jobs soared. And find a National Shrine at Chicago’s oldest Mexican parish** before discovering a Chicago landmark, Calumet Park Field House.


Taste of the Neighborhoods

Travel Chicago and savor cuisines from lands near and far. This delectable journey features two different restaurants serving assorted small-plate samplers. Taste the nuances; talk exotic ingredients, techniques, and cultures; and collect recipes. Dessert or sweets at the last stop are the cherries on top. Destinations change every two months; restaurants are determined about three weeks before tour dates. Seats go quickly on this popular tour. Please call for details.

The White City

During the 1893 World’s Columbian Exposition, “The White City” enthralled 27 million visitors. You’re transported there through the photographic slide presentation at the Chicago Cultural Center. In Jackson Park, picture the fair’s hundreds of buildings, and see the Statue of the Republic and other original sites. After a bite, you’re off to the Chicago History Museum, where the elevated train that transported fairgoers to the exposition is on view.

Photo of a gilded sculpture in a park.

Uptown, Andersonville & Lincoln Square

These Far North Side neighborhoods. Time is allotted to explore Clark Street in Andersonville and the shops along Lincoln Avenue in Lincoln Square.

Wicker Park & Ukrainian Village

You’ve hit upon two distinct West Town neighborhoods. Wicker Park’s towering Victorian-era mansions and Ukrainian Village’s Eastern European accents hint at divergent origins. Soak up old- and new world history and culture at Ukrainian National Museum and a local church.** Shop fashionable boutiques in the heart of the oh-so-trendy Wicker Park, along Damen and Milwaukee avenues. Meet up for a revealing, walking exploration of Wicker Park and area architecture.

Wicker Park

Chicago Boat Tours

There are Chicago boat tours, and river tours where you can enjoy fun and food on the water. You can sail away in a custom river boat and enjoy the waves on the Chicago River or Lake Michigan. The views can be just stunning. You can gather with your friends, family or significant other and tour the city from a different point of view.

Weather permitting, these River and boat tours can involve viewing the many unique architectural styles that Chicago has.  Chicago Boat Tours and cruises can give you a chance to relax and sight see in this beautiful city. You will have a variety of boating companies to choose from along with different sizes of boats and ships.

You will definitely be able to find a ship that will cater to your needs. Some may be river boats and some may be larger boats that can also offer a cruise and dinner on Lake Michigan. Whatever your choice may be, it’s a great way to spend time on the water.

People love to go out on Lake Michigan especially when the weather gets warm. Chicago also has cruise boats that offer different themes with their cruises. Some are sightseeing architectural cruises. Some themes involve firework viewing during the cruises. These different themes can allow you to relax and enjoy the entertainment, and night views of the city. Others themes can involve a sightseeing sunset cruise if you desire to spend a romantic evening on the water.

Some cruises may just involve cruising under the moonlight and enjoying the presence of a loved one. You can also explore the city on one of the many River Cruises. These tours and cruises are seasonal as the River and Lake Michigan freezes in the winter. However in the spring, summer and fall the lake and river are alive with plenty of action and touring boats. The ships are very busy catering to their customers needs for a good time, and a terrific sightseeing and tour experience.