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Chicago Loop Culinary & nightlife

Our most recommended Chicago Loop Culinary & nightlife

Chicago: Secret Food Tour

1. 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.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

2. 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

3. 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: Deep-Dish Pizza and Local Food Walking Tour

4. Chicago: Deep-Dish Pizza and Local Food Walking Tour

Immerse yourself in an exploration of Chicago’s outstanding food culture. Navigate through the Loop district, which is buzzing with activity, as your guide brings you straight to the vendors and restaurants they love most. Taste some of the local staples, including the world-famous deep dish pizza. Pass by iconic places like the Chicago Riverwalk and get to grips with the evolution of the city, as immigrants brought their culinary influence from all over the world. Get to know family shops owned for generations and learn the origins behind the Windy City's most beloved street eats. Enjoy a local street food staple, perhaps the famous Chicago-style hot dog or Italian beef sandwich. And, of course, a food tour of Chicago is not complete without a bite of the iconic deep-dish pizza. Try a slice and top it off with a traditional sweet treat for a complete foodie experience.

Chicago: Architecture and Food Walking Tour with Tastings

5. Chicago: Architecture and Food Walking Tour with Tastings

Experience the best of Chicago on a guided walking tour that explores the city's architecture and food culture. Your 2-part walking tour begins by exploring the heart of Downtown Chicago. Join your guide as you discover the city's architectural highlights, both old and new. Admire views of the Chicago River, see Chicago's City Hall, the Wrigley Building, the Water Tower, Cloud Gate, and much more. Then, hit the Central Loop, where locals go to grab their favorite foods. Sample some of Chicago's famous fare and learn about the history behind street food staples in the Windy City. Let your local guide show you the how-tos (and how-not-tos) of legendary dishes, from deep dish pizza to sandwiches, to a loaded hot dog. Listen as they entertain you with fascinating stories of the everyday immigrant chefs and vendors responsible for Chicago's eclectic food scene. By the end of the tour, you'll have a deep appreciation for both the evolution of this city and the role food has played in the lives of its residents.

Chicago: Private Neighborhood Food Tour with a Local Guide

6. Chicago: Private Neighborhood Food Tour with a Local Guide

Discover the best eats in Chicago on a private food tour with a local guide. Explore areas like Downtown Chicago and the Loop, visit a local coffee roastery, or try sweets at a chocolate factory. Enjoy a completely custom itinerary, created just for you and your group’s taste buds. Following pickup from your address in Chicago, meet your guide to start your personalized food journey. Choose specific spots to see or let your guide create a custom itinerary that fits you and your group’s interests, budget, mobility, and time. Try an iconic deep-dish pizza, go behind the scenes at a local coffee roastery, or try some tasty desserts at a chocolate factory. Typically, tours spend most of their time in and around downtown Chicago, but the possibilities are endless.

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What people are saying about Chicago Loop

Justin did a wonderful job giving a feel for Chicago and its history--loved it!

Justin was a wonderful knowledgeable tour guide. We had a great time!

Just a super time eating great food and learning some local history.

it was fun and learned tons of stuff about the city!

Our guide was Amazing!!!! Food was delicious as well