Chicago is a city that’s meant to be explored on foot. From its stunning architecture to its vibrant neighborhoods, there’s no better way to experience the Windy City than on a walking tour. But with so many options to choose from, it can be overwhelming to pick the best one. That’s why we’ve done the research for you and narrowed it down to the 3 best walking tours in Chicago. Whether you’re a history buff, a foodie or just looking for a fun day out, these tours have something for everyone. So, lace up your shoes and get ready to discover the best of Chicago on these amazing walking tours.

The 3 Best Walking Tours in Chicago

1. Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
2. Walking Tour of Historic Chicago Pubs in River North and the Loop
3. Walking Tour of Chicago Loop the Home of the Modern Skyscraper

The 3 Best Walking Tours in Chicago

1. Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Discover the fascinating history of Chicago’s Prohibition Speakeasies on this guided tour. With the option to choose between a walking tour or a bus tour, you’ll visit three to four hidden bars either downtown or in the neighborhoods. Learn about the notorious gangsters and elites who frequented these bars during Prohibition and enjoy drink recommendations at each location. The tour includes a professional guide, entry to three to four Speakeasies (depending on the option chosen), a professional driver for the bus tour, and the option to purchase food and drinks. Please note that this tour is not suitable for individuals under the age of 21.

2. Walking Tour of Historic Chicago Pubs in River North and the Loop

This walking tour takes you on a journey through the iconic historic pubs in River North and the Loop. You’ll enjoy a four-hour guided experience, starting at Marquette Building at 140 S Dearborn St, and walk through the city’s oldest taverns and breweries.

Your expert guide will share interesting facts and stories about each establishment, explaining the significance it has played in the city’s social and political history. From the beer selection to the atmosphere, you’ll appreciate the unique character and charm of each pub.

Included in the tour are transit tickets, alcoholic beverages, and snacks. The tour ends with a drink and more stories at Monk’s Pub, a famous pub located at 205 W Lake St.

Please note that this experience requires moderate physical fitness as not all train stations have elevators. It is not recommended for those with back problems, heart problems or other serious medical conditions.

If you need to cancel, you can do so up to 24 hours in advance for a full refund. We hope you join us for this fantastic walking tour of the historic Chicago pubs in River North and the Loop.

3. Walking Tour of Chicago Loop the Home of the Modern Skyscraper

The Walking Tour of Chicago Loop the Home of the Modern Skyscraper is a must-do experience for architecture enthusiasts and history buffs. Led by a lifelong resident of the city, this small-group tour takes you on a journey through the heart of downtown Chicago. You’ll explore notable landmarks such as the Rookery Building and the Chicago Cultural Center, the latter of which boasts the world’s largest Tiffany dome. Learn about the city’s urban planning and modern history while discovering its tucked-away architectural highlights. This tour includes transit tickets, snacks, and the guidance of an expert local guide. With a maximum group size of just eight people, you’re sure to get a personalized experience. Meet your guide at the Fine Arts Building at 10:00 AM, and end your tour at the Chicago Cultural Center.

The Most Frequently Asked Questions About Chicago

Chicago is a bustling city known for its world-renowned architecture, delicious food, and lively culture. However, like any other city, visitors and tourists tend to have questions about their destination. In this post, we will answer some of the most frequently asked questions about Chicago to help you plan your next visit.

1. What is the best time to visit Chicago?

Chicago is a city with a history of harsh winters, but the summer is the best time to visit. The months between June and August offer comfortable temperatures, making it perfect for outdoor activities and festivals. The city is also lively with street fairs, outdoor concerts, and beach activities. Spring and fall are also popular times to visit, but the weather can be unpredictable, especially in April and October.

2. Where are the best places to stay in Chicago?

Chicago has plenty of accommodation options, from luxury hotels to budget-friendly hostels. The Magnificent Mile, the downtown area along Michigan Avenue, is a popular place to stay. It offers easy access to some of the city’s top attractions, including the Art Institute of Chicago and Millennium Park. The River North and West Loop neighborhoods are also trendy and offer a range of bars and restaurants. If you are looking for a more relaxed atmosphere, Lincoln Park and Lakeview offer peaceful surroundings and beautiful parks.

3. What are the must-see attractions in Chicago?

Chicago has a lot to offer for visitors of all ages. Here are some of the must-see attractions:

• The Willis Tower (formerly known as Sears Tower) – Once the tallest building in the world, it offers panoramic views of the city from its Skydeck.
• The Art Institute of Chicago – It has a vast collection of art from around the world, including iconic paintings such as Grant Wood’s “American Gothic.”
• Museum Campus – It includes some of the city’s top museums, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.
• Millennium Park – It’s a beautiful park featuring landmarks such as the iconic Cloud Gate, also known as the “Bean,” and the Jay Pritzker Pavilion, a unique outdoor amphitheater.
• Navy Pier – It’s an entertainment destination that offers attractions such as the Ferris wheel, IMAX cinema, and a variety of restaurants and shops.

4. What are the best food options to try in Chicago?

Chicago is known for its unique and delicious food. Here are some local dishes to try:

• Deep-dish pizza – A Chicago-style pizza that features thick crust, lots of cheese and tomato sauce, and various toppings. Some of the popular pizza places include Lou Malnati’s and Giordano’s.
• Chicago-style hot dog – A hot dog topped with yellow mustard, sweet pickle relish, chopped onions, tomato slices, a pickle spear, and peppers. You can find it at various hot dog stands in the city.
• Italian beef sandwich – Thinly sliced roast beef served on a roll with hot peppers or sweet peppers, and dipped in jus. Some of the popular places to try it are Al’s Beef and Portillo’s.
• Garrett Popcorn – A family-owned popcorn company known for their “Chicago Mix” – a blend of caramel and cheese popcorn.
• Chicago-style steak – Chicago has plenty of steakhouses, but some of the popular ones are Gibsons Bar & Steakhouse and Gene & Georgetti.

5. How do I get around in Chicago?

Chicago has a well-connected public transportation system, including trains and buses. The “L” train is the most popular mode of transportation, offering affordable and convenient transport throughout the city. Taxis and ride-share services such as Uber and Lyft are also available. Walking or biking is another great option, especially in downtown areas where attractions are close together. If you plan on driving, be prepared for traffic, and make sure to research parking options beforehand.

6. Is Chicago safe for tourists?

Like any major city, Chicago has its share of crime. However, most of the crime occurs in specific areas that are known for being high-risk. As long as you avoid those areas and take necessary precautions, you should have a safe and enjoyable visit. Always be aware of your surroundings, keep your valuables safe, and avoid walking alone at night.

7. What events or festivals are happening in Chicago?

Chicago has a packed calendar of events and festivals throughout the year. Some of the popular festivals include the Chicago Blues Festival, Lollapalooza, Chicago Jazz Festival, Taste of Chicago, and the Chicago Air and Water Show. During the holiday season, you can also visit the famous Christkindlmarket, an outdoor German market that sells food, crafts, and gifts.

Conclusion

Chicago is a vibrant and exciting city with something for everyone. We hope that our frequently asked questions guide has helped you plan your visit and make the most of your time in the “Windy City.” Remember to always check the latest COVID-19 safety guidelines before traveling and enjoy exploring the best of what Chicago has to offer.

The 3 Best Walking Tours in Chicago: FAQs

Chicago is a beautiful city with stunning architecture, rich history, delicious food, and lively culture. There’s so much to see and explore that it can be overwhelming for visitors to decide where to start. One of the best ways to experience the best of Chicago is by taking a walking tour. In this blog post, we will answer the most frequently asked questions about the 3 best walking tours in Chicago.

1. What are the 3 best walking tours in Chicago?

Chicago is a city that’s full of life and excitement, and it’s not surprising that there are several walking tours that are highly recommended. The 3 best walking tours in Chicago are:

a. The Chicago Architecture Foundation River Cruise

The Chicago Architecture Foundation River Cruise is a 90-minute tour that takes visitors on a journey along the Chicago River to view the city’s famous architecture. The tour is led by expert guides who share the history and behind-the-scenes stories of Chicago’s most iconic buildings. Visitors are also treated to stunning views of the city’s skyline while enjoying a relaxing boat ride.

b. The Chicago Crime Tours

The Chicago Crime Tours is a tour that explores Chicago’s notorious past. Visitors get to see the locations of famous gangster hangouts and the spots where some of the most notorious crimes in Chicago’s history took place. The tour is unique and informative, and visitors get to learn about the dark side of Chicago’s past.

c. The Chicago Food Planet Food Tours

The Chicago Food Planet Food Tours is a tour that explores Chicago’s diverse food culture. Visitors get to sample some of the city’s most delicious foods while learning about the history and culture behind them. The tour is led by expert guides who provide insights into the background and preparation of each dish.

2. How much do the walking tours cost?

The cost of the walking tours will vary depending on the tour and the tour company. The Chicago Architecture Foundation River Cruise costs $50 for adults, while the Chicago Crime Tours cost $41 for adults. The Chicago Food Planet Food Tours cost between $50-$60 per person depending on the tour.

3. How long do the walking tours last?

The length of the walking tours will vary depending on the tour and the tour company. The Chicago Architecture Foundation River Cruise is a 90-minute tour, while the Chicago Crime Tours lasts for 2 hours. The Chicago Food Planet Food Tours last for approximately 3 hours.

4. Are the walking tours suitable for children?

All three walking tours are suitable for children. However, some tours may not be recommended for very young children due to the length of the tours or the subject matter. Visitors should check with the tour company for specific information regarding age restrictions.

5. Do visitors need to make reservations for the walking tours?

Yes, visitors are advised to make reservations for the walking tours in advance. This is to ensure that they secure a spot on the tour, especially during peak seasons. Reservations can be made online, by phone, or in person, depending on the tour company.

6. Are the walking tours accessible for people with disabilities?

Most tour companies will make necessary accommodations for people with disabilities. Visitors should contact the tour company before the tour to discuss their specific needs.

7. What should visitors wear and bring for the walking tours?

Visitors should wear comfortable walking shoes and dress appropriately for the weather. Bringing a water bottle, sunscreen, and a hat is also recommended, depending on the tour.

8. Can visitors take pictures during the walking tours?

Yes, visitors are encouraged to take pictures during the walking tours. However, some tours may have restrictions on photography in certain areas. Visitors should check with the tour guide for specific information regarding photography.

9. Are the walking tours worth it?

Absolutely! The walking tours are an excellent way to experience the best of Chicago’s history, culture, and food. Visitors get to see the city up close and personal, and they get to learn about the city’s rich and diverse history.

Conclusion

In conclusion, the 3 best walking tours in Chicago are a great way to discover the many delights of the Windy City. Visitors can learn about the city’s architecture, past, and food culture through these fantastic tours. We hope this blog post has been informative and helpful in answering your most frequently asked questions about the 3 best walking tours in Chicago. Don’t hesitate to book your tour and discover the best of this vibrant city!