8 Popular Guided Tours in Chicago
Arriving in Chicago and want to get to know the Windy City up close? Instead of trying to figure out where to start exploring, join guided tours that will show you all the must-sees in the birthplace of skyscrapers on Lake Michigan.
Here are 8 tours in Chicago that will offer you everything you need to see and experience in the big city, in an engaging and comprehensive way ????
- Chicago River Cruise with Skyscraper Tour
- Guided Sightseeing Tour of Chicago's Most Famous Sites + Tastings
- Guided Tour of Downtown Chicago Following the Gangsters
- Guided Riding Tour in Chicago (Segway, Electric Bikes or Bicycles for the Fit Ones)
- Guide at the Art Institute of Chicago
- Guided Tour Following Movies and Series Filmed in Chicago
- Guided Culinary Tour in the Food Scene of Downtown Chicago
- A Sweet Guided Culinary Tour Following Chicago's Donuts
Tour 1: Sailing on the Chicago River and Lake Michigan, and a Guide on the City's Skyscrapers
The Chicago River flows through the heart of the city, between the downtown (or the Loop) and the Magnificent Mile. Along the river, there's an impressive row of unique and beautiful skyscrapers that showcase modern architecture from the late 19th century to the early 21st century. A cruise on the Chicago River is one of the most popular guided tours in the city and usually offers commentary focused on the historic skyscrapers lining the riverbank.
Click here for a river cruise with a guided tour of the city's towers…
There are all sorts of cruises, both short and longer ones. There's a cruise only on the river and there's also one that combines a journey along the city's shoreline on Lake Michigan (there are also cruises solely on Lake Michigan). On the longer cruises, you can also learn about the skyscrapers that are distant from the river, including the Sears Tower and the John Hancock Center.
Click here for a cruise on Lake Michigan and a guided tour of Chicago's architecture…
Tour 2: Guided Sightseeing Tour of Chicago's Most Famous Sites + Tastings
The sightseeing in Chicago is one of the heaviest burdens on the neck. This is a fascinating city with a large number of sites and attractions from Millennium Park, through the Loop Towers and of course, the Magnificent Mile. There are many guided walking tours in downtown Chicago that encompass all the city's main attractions. Guided walking tours are a great way to see Chicago quickly and efficiently, reaching all the must-see spots in downtown.
Click here for a guided walking tour in downtown Chicago + tastings of the city's unique foods…
Tour 3: Guided tour in downtown Chicago following the gangsters
Chicago is a historic city associated with many things, but nothing is as intriguing as the mafia that took over the city in the early 20th century during the Prohibition Era. The city has its own mythology regarding gangsters, led, of course, by Al Capone from New Jersey, who is considered the most famous gangster to have operated in the city and who led the Chicago Outfit.
The mafia's defining event in the city was the Valentine's Day Massacre on February 14, 1929, when Capone's men murdered the soldiers of his bitter rival, George “Bugs” Moran, head of the Irish gang. Tours following the gangsters, the mafia, and the victims of the violent events in central Chicago are very popular and are an integral part of the city's pop culture in general.
Tour 4: Guided Ride Tour in Chicago (Segway, Electric Bikes or Regular Bikes for Those in Shape)
Chicago is an almost perfect city for guided ride tours. The city offers a huge selection of such tours on Segways, electric bikes, and of course regular bikes that also incorporate a bit of physical activity. Most tours take place along Lake Michigan, from Soldier Field Stadium and the Field Museum, through Grant Park and Millennium Park to the Navy Pier.
Click here for a guided Segway tour in Downtown Chicago…
Tour 5: Guided Tour at the Art Institute of Chicago
The Art Institute of Chicago is one of the largest museums in the United States, boasting one of the most magnificent collections of European and especially American art. The most famous and significant painting by the American giant Edward Hopper, “Nighthawks” or known as the Night Cafe, from 1942, is one of the great and well-known paintings by American artists. A strong contender with Hopper's painting is Grant Wood's masterpiece “American Gothic” from 1930. This painting, depicting two stern and devout rural folk, is considered an American classic.
The European collection at the museum features some of the most famous artworks in the world. Leading the display is the most famous pointillist masterpiece “La Grande Jatte” by Georges Seurat, the stunning landscape painting “The Bay of Marseille, Seen from L'Estaque” by Paul Cézanne, the impressionist masterpiece “Paris Street; Rainy Day” by Gustave Caillebotte, and Vincent van Gogh's iconic painting “Bedroom in Arles” from 1888. The institute offers a wealth of especially fascinating guided tours that delve into the richness of the collection.
Click here for skip-the-line entry + guided tour of the Art Institute of Chicago…
Tour 6: Guided Tour Following the Movies and Series Filmed in Chicago
Chicago is one of the hottest spots for Hollywood movies. Many famous films have been shot in the city, like Home Alone filmed in the suburbs, and all of John Hughes' '80s movies (a nod to Molly Ringwald fans and '80s enthusiasts).
A super cool guided tour traces the locations of movies and series filmed in downtown Chicago, including The Dark Knight, the successful installment in Christopher Nolan's Batman series. Another location closely associated with Chicago is Buckingham Fountain, which prominently features in the opening of the cult series Married with Children.
Click here for a guided tour following the series and movies filmed in Chicago…
Tour 7: Guided Culinary Tour of Downtown Chicago's Food Scene
Chicago is an empire of American cuisine, often on the calorie-rich side of the food map. Due to the waves of Irish, Polish, German, and particularly Italian immigrants in the late 19th century, the city boasts a stunning fusion of dishes including the pizza pie (or Deep Dish Chicago-Style Pizza), a huge variety of hearty meat sandwiches, and all kinds of sausages like the Chicago-style and Polish sausage, among others.
The city is packed with fantastic restaurants offering dishes light-years away from the American fast-food scene (it is also the birthplace of McDonald's, but that's not on the tours). There is a variety of culinary tours in the city center, offering tastings of signature dishes from city restaurants. There are also tours in Chicago's Chinatown known for its excellent Chinese restaurants.
Click here for a guided culinary tour of all the most unique spots in downtown Chicago…
Tour 8: A Sweet Guided Culinary Tour Following Chicago's Donuts
Another entirely popular culinary tour is Chicago's Great Donut Tour. If you haven't filled up on pizza pie or Polish sausages, or if you still have a special spot for something sweet, Chicago is a donut empire offering every kind imaginable. This great donut tour combines tastings of the local donut scene, including more traditional and veteran places, alongside modern cafes and bakeries that offer new takes on the sugary, fried doughy treat.
Click here for a sweet culinary tour following Chicago's special donuts…
6 Tips from Guy for Fantastic Tours in Chicago!
Chicago, the formidable Windy City on the shores of Lake Michigan, is the great metropolis of the vast expanse between New York City and Los Angeles that we know as the United States. Chicago birthed skyscrapers in the late 19th century with modern construction techniques that were later adopted in Manhattan, shaping the stunning skylines of both cities.
Since then, Chicago has evolved into an important cultural, transportation, and culinary hub. Today's city is buzzing with life, offering a huge variety of attractions in the Loop (Chicago's downtown) and on the Magnificent Mile. The city boasts excellent food, exceptionally fun shopping, and thrilling observation decks atop the Willis Tower (formerly Sears Tower) and the John Hancock Center.
Guy's Tips
- How to choose the right tour for you? – Visiting the Art Institute of Chicago could be a dream for one person and quite boring for another (both American Gothic and Edward Hopper's Nighthawks are displayed there, it's an amazing museum for art lovers????). Pick a tour theme that interests you. If Georges Seurat's pointillism doesn't make your day, there's really no point in paying for an entrance ticket + someone to explain the unique point-building method of the Grande Jatte painting. Choose a tour that truly interests you, that's how you'll enjoy it the most.
- English Proficiency – If your English is decent, the tour options in Chicago are limitless. Guided tours are becoming incredibly trendy all over the USA and Europe as a convenient and efficient way to see big cities. Chicago tours focus on architecture and food and offer a fun experience mingling with tourists from all over the world, with guides proudly showcasing their city.
- Comfortable Shoes – We know appearances matter, but do your feet a favor and wear comfortable closed shoes for each tour (both walking and riding tours). The cumulative walking in Chicago can lead to sore muscles.
- Dress Appropriately – Tours in Chicago are held throughout the year, both outdoors and indoors. Summer days can be hot, so it's advisable to come in light clothes. Winter is freezing, so it's best to come prepared with warm clothing that can be easily removed when entering indoor spaces.
- Backpack with snacks and drinks – Guided tours are kind of a structured group setting, designed for everyone's comfort on one hand, yet run on a fixed schedule on the other. These tours involve walking and, even more tiring, the need for listening and staying focused. To avoid holding up the group or staying hungry, it's a good idea to bring a backpack with water, drinks, and some snacks in case hunger strikes.
- Read a bit ahead about your destination – Nothing whets the appetite like nibbling on some information the night before about the tour destination. If you love traveling and getting to know places in depth, some basic prep will give you orientation. When you reach your destination, you'll already understand what the guides are talking about and have a clear context.
