Chicago Loop
Culinary & Nightlife

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Our most recommended Chicago Loop Culinary & Nightlife

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

1. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

2. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

Chicago: Secret Food Tour

3. Chicago: Secret Food Tour

Sample the culinary delights of Chicago with the help of a fun and enthusiastic foodie guide. Be amazed by the city's eclectic mix of architecture and public art along the way. Taste delicious bites as you explore the city's central Loop district for 3 hours. Get better acquainted with what sets this friendly Midwest metropolis apart from other destinations and get a great insight into the art, architecture and everyday life in the city. Benefit from your guide's local knowledge and get tips to help you sightsee and explore the food and dining scene some more in your own time.

Frequently asked questions about Chicago Loop Culinary & Nightlife

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Which Chicago Loop Culinary & Nightlife are taking additional COVID-19 precautions?

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Other Sightseeing Options in Chicago Loop

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What people are saying about Chicago Loop

My friend and I were on a girls trip to Chicago, and booked this tour, as it had very good reviews. We were not disappointed. We were the only 2 on the tour, Denice was the best host. She was funny and very informative. The tour does not only involve food, but visits to different buildings in between eats. It was fun to hear the history of the buildings. The library was amazing. We were stuffed after the food tour so plan accordingly. We canceled our dinner reservations! Food was deep dish pizza, popcorn, hot dog, chopped beef sandwich, and brownie. All were amazing!

Had a great time on our food tour! It’s a great way to learn about foods that were improved upon by this city, some of the history and see a few blocks of downtown.

Loved our food tour. Guide Julia was great. Very knowledgable and entertaining. What a nice way to learn and eat some of Chicago food. Would highly recommend it.

Fun, informative, very tasty tour. Dylan, the guide, was knowledgeable and super fun.

Justin was phenomenal! So enthusiastic about the city. Made it so fun! Also, the food