Chicago is a vibrant city with a bustling nightlife, and one of the best ways to experience it is by taking part in a pub crawl. Whether you’re a local looking for a new spot to hang out with friends or a visitor eager to explore the city’s bar scene, there’s a Chicago pub crawl to suit your preferences. In this post, we’ll explore some of the best pub crawls in Chicago, from classic routes to new and innovative tours. So grab a drink and let’s dive into the Windy City’s pub crawl scene.

The 3 Best Chicago Pub Crawls

1. Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
2. Haunted Chicago Ghost and Pub Walking Tour
3. Private Speakeasy Pub Crawl in Chicago with Local Historian

The 3 Best Chicago Pub Crawls

1. Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Discover the fascinating history of Prohibition in Chicago with the Chicago: Prohibition Speakeasies tour. This guided tour takes you to 3 or 4 of Chicago’s famous Prohibition Speakeasies where you’ll be able to learn about the city’s notorious gangsters and high society. The tour is available in two options: a Hidden in Plain Sight walking tour Downtown, or a Chicago Prohibition neighborhood bus tour. Both options come with a professional guide and entry to the Speakeasies, with the bus tour including a professional driver. You’ll have the chance to purchase food and drink at each of the speakeasies, with drink recommendations provided to enhance your experience. This tour is not suitable for people under 21 years old.

2. Haunted Chicago Ghost and Pub Walking Tour

Join the Haunted Chicago Ghost and Pub Walking Tour for a unique experience exploring the city’s spooky hidden corners. Led by a costumed guide dressed as a Flapper or 1920s Gangster, you’ll journey on a mile-long walk while learning about Chicago’s haunted past. You will stop at three different bars for drinks (at your own expense) and hear the secret tales behind each location. This tour is perfect for those looking to discover forgotten cemeteries and lingering spirits. The tour starts at Lincoln Station and ends at either Racine Plumbing Bar & Grill or a nearby spot. Don’t miss out on this haunted pub crawl adventure.

3. Private Speakeasy Pub Crawl in Chicago with Local Historian

Step back in time to the roaring twenties with a private speakeasy pub crawl in Chicago led by a local historian. Dressed in period attire, your guide will take you on a journey through secret entrances to speakeasies once frequented by notorious gangsters such as Al Capone. Learn about the colorful history of prohibition-era Chicago while sipping on prohibition-era cocktails (additional cost). Guests are welcome to dress up in period clothing and get fully immersed in the experience. This private tour includes convenient transportation with hotel pick-up and drop-off, bottled water, and of course, fascinating firsthand accounts of gangsters and bootlegging in Chicago. Join us and experience Chicago like never before with this exclusive pub crawl.

Exploring the City of Chicago: Tourists’ Frequently Asked Questions

Chicago, also known as The Windy City, is a vibrant and diverse city located in the Midwest region of the United States. It is the third-most populous city in the country and has a rich history that attracts millions of visitors every year. If you’re planning a trip to Chicago, you might have some questions about the city. Don’t worry, we’ve got you covered. Here are some of the most frequently asked questions by tourists about the city of Chicago.

1. What’s the best time to visit Chicago?

Chicago has a diverse climate, characterized by cold winters and hot summers. The best time to visit Chicago is during the summer months, from June to August. During this time, the weather is warm and there are numerous outdoor events and festivals, making it the busiest and most tourist-friendly season. If you are looking for lesser crowds and better deals, the spring and fall seasons are also great options to explore the city.

2. What must-see attractions should I visit in Chicago?

Chicago boasts numerous must-see attractions that cater to different interests. Here are some of the most popular ones:

(i) The Willis Tower (formerly known as Sears Tower)

The Willis Tower is one of the most iconic landmarks in Chicago and the Western Hemisphere. It stands at 110 stories tall and was the tallest building in the world when it was completed in 1973. The Skydeck observation deck on the 103rd floor offers a spectacular view of the city.

(ii) Millennium Park

Millennium Park is an urban park located in the heart of Chicago. It features various art installations, gardens, fountains, and landscaped greenery. The highlight of the park is the Cloud Gate sculpture, also known as “The Bean”, which is a must-see for tourists.

(iii) Museum Campus

Museum Campus is a park located in the South Loop neighborhood of Chicago. It comprises three famous museums: The Field Museum, the Shedd Aquarium, and the Adler Planetarium. Visitors can enjoy a full day exploring the exhibits, artifacts, and interactive displays.

(iv) Navy Pier

Navy Pier is a popular tourist destination located on the shoreline of Lake Michigan. It features various family-friendly attractions such as a Ferris wheel, an IMAX theater, and boat tours. Visitors can also enjoy a variety of restaurants and shops.

3. What’s the best way to get around Chicago?

Chicago has a well-connected public transportation system. The Chicago Transit Authority (CTA) offers “L” trains and buses that can take you to most parts of the city. The “L” train has several lines that run 24/7 and cover most of the popular tourist spots.Taxis and ride-sharing services such as Uber and Lyft are also available for those who prefer a more direct mode of transportation. Biking is also a popular option, with several bike rental stations located throughout the city.

4. What are some budget-friendly activities to do in Chicago?

Chicago has plenty of affordable attractions for budget-conscious tourists. Here are some suggestions:

(i) Chicago Riverwalk

The Chicago Riverwalk is a public promenade that runs along the Chicago River. Visitors can enjoy a leisurely stroll and view the city’s iconic architecture. They can also sit down and enjoy a picnic or a drink at one of the many outdoor cafes.

(ii) Lincoln Park Zoo

The Lincoln Park Zoo is a free zoo located in the Lincoln Park neighborhood of Chicago. It features a wide variety of animals, from lions to penguins, and is a great attraction for families with children.

(iii) Millennium Park

Millennium Park is not only an attraction for art lovers, but also budget-friendly. Visitors can enjoy the art installations, outdoor concerts, and free movie screenings. There is also a playground for kids to enjoy.

5. What’s the best way to experience Chicago’s food scene?

Chicago is known for its diverse and delicious food scene, ranging from deep dish pizza to Hot Doug’s iconic hot dogs. Here are some tips to fully experience it:

(i) Take a food tour

Food tours are a great way to experience the city’s different neighborhoods and local cuisines. There are various tours available, ranging from pizza tours to food truck tours.

(ii) visit a street festival

Chicago hosts several street festivals throughout the year that celebrate the city’s diverse food culture. The Taste of Chicago festival is one of the most popular ones and offers a variety of food options from different cuisines.

(iii) Visit local food markets

Chicago has several local food markets that offer a wide variety of cuisines and flavors. Some notable examples include the Chicago French Market, the Maxwell Street Market, and the Pilsen Community Market.

In conclusion, Chicago is a diverse and vibrant city that has something for everyone. Whether you’re a foodie, history buff, art lover, or simply looking for a fun vacation spot, Chicago has it all. By following these tips and recommendations, you can make the most out of your visit and create unforgettable memories.

How to Spend Your Time as a Tourist in Chicago

Chicago, also known as the Windy City, is a bustling metropolis with a rich history and thriving cultural scene. As a tourist, there’s no shortage of things to see and do in Chicago, but with so many options, it can be overwhelming to decide where to start. In this guide, we’ll break down some of the must-see attractions and activities to help you make the most of your time in the city.

1. Visit the world-famous attractions

Chicago is home to some iconic tourist attractions that shouldn’t be missed on your visit. One of the most famous is the Willis Tower, formerly known as the Sears Tower, which was once the tallest building in the world. Take a trip up to the Skydeck on the 103rd floor for an incredible panoramic view of the city. Another iconic attraction is the Navy Pier, a boardwalk-style entertainment complex on Lake Michigan that’s home to a Ferris wheel, shops, restaurants and more.

2. Explore the city’s architecture

Chicago is known for its stunning architecture, from the historic skyscrapers of the Loop to the modern designs of the city’s skyline. To explore the architectural history of the city, take a river cruise or walking tour led by an expert guide. The Chicago Architecture Center is also a great place to learn more about the city’s design history and famous architects.

3. Experience the city’s culture

Chicago has a thriving arts and cultural scene, with world-renowned museums, galleries, theaters, and music venues. The Art Institute of Chicago is one of the largest and oldest art museums in the country, with an extensive collection of works from around the world. For music lovers, the Chicago Symphony Orchestra and the Chicago Theatre host regular performances and concerts. And don’t forget to check out the Chicago Cultural Center for free events and exhibits.

4. Indulge in Chicago’s culinary scene

Chicago is known for its unique and diverse food scene, from deep-dish pizza to hot dogs to Italian beef sandwiches. To truly experience the city’s culinary offerings, consider taking a food tour or visiting some of the local food markets, such as the Chicago French Market or the Maxwell Street Market. Don’t leave without trying some classic Chicago-style pizza from one of the city’s famous pizza spots, like Lou Malnati’s or Giordano’s.

5. Enjoy the outdoors

Chicago has plenty of green spaces and parks to enjoy, even in the heart of the city. If you’re visiting during the summer months, head to the beaches along Lake Michigan for some fun in the sun. Alternatively, visit one of the city’s many parks, such as Millennium Park or Grant Park, for a picnic or a stroll. For a more active outdoor experience, rent a bike and ride along the lakefront trail or take a kayak tour along the Chicago River.

6. Discover the city’s neighborhoods

Each neighborhood in Chicago has its own unique character and charm, so take some time to explore beyond the city center. From the trendy boutiques of Wicker Park to the historic homes of Hyde Park, there’s something to discover around every corner. Consider taking a guided tour or even renting a bike to explore the different neighborhoods at your own pace.Chicago is a vibrant and exciting city with endless options for things to see and do. By following these tips and exploring some of the city’s top attractions and hidden gems, you’re sure to have an unforgettable trip.