Top Chicago Dining Experiences

Dining Experiences

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City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

2 hoursFree Cancellation

Likely to Sell Out

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

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City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

4.0

(388)

from $63

Member Pricing

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

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Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

2 hoursFree Cancellation

Member Pricing

Step into Chicago’s coolest hidden bars on a mid-century cocktail adventure! Join a local guide to discover vintage lounges, secret speakeasies, and retro bars most tourists miss. Savor expertly crafted cocktails (own expense), hear untold stories of the city’s nightlife boom, and soak in stylish decor straight from the 1950s and 60s. This small-group tour is perfect for cocktail lovers, architecture buffs, and anyone seeking an off-the-beaten-path night out in the Windy City.

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Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

1 hour 30 minutesFree Cancellation

Likely to Sell Out

City Cruises Chicago: River Architectural Lunch Cruise

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

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City Cruises Chicago: River Architectural Lunch Cruise

2 hoursFree Cancellation

4.4

(44)

from $116

Member Pricing

Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.

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Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

2 hoursFree Cancellation

Member Pricing

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

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City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

2 hoursFree Cancellation

Member Pricing

In the heart of Chicago, near Wrigley Field, a culinary adventure awaits. Led by Rakhi, a professionally trained chef and Le Cordon Bleu graduate with experience working with Bobby Flay, this private cooking class immerses you in the rich flavors of Italian-American cuisine. Over 2.5 hours, you'll learn to prepare iconic dishes such as Chicken Vesuvio, hot fried chicken, and homemade desserts, all while enjoying a relaxed and interactive atmosphere. With the chance to tailor your menu, every class becomes a unique experience that celebrates Chicago's vibrant food culture. Gather your friends or family for a memorable evening of cooking and dining together.

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Private Chicago Cooking Class with Le Cordon Bleu Chef

2 hours 30 minutesFree Cancellation

5% savings

from

$149$142

Member Pricing

Savor the flavors of Mexico’s Yucatan Peninsula, right in Chicago—and feel like a local when you dine in your host’s own home—during this small-group dinner experience. Be sure to come hungry: alongside a small group of diners, you’ll savor a multi-course menu of Yucatan classics, from a tropical starter to pibil tacos and beyond. In between, enjoy cocktails and the chance to converse with your host and fellow guests.

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Yucatan Delights by a Michelin Star-Trained Chef in Chicago

2 hoursFree Cancellation

Member Pricing

Learn the secrets of making one of Mexico’s most celebrated dishes during this beginner-friendly, local-hosted cooking class. Meet your Michelin-trained chef guide at her home, enjoy a refreshing hibiscus agua fresca upon arrival, and roll up your sleeves. Your guide will break down the steps to make an authentic mole sauce, and share tips as you go. Finally, sit down to enjoy your tasty and traditional meal.

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Learn To Make Mole The Real Mexican Way Before Lunch

2 hoursFree Cancellation

Member Pricing

Little Diners Crew invites young food enthusiasts aged 4-12 to embark on culinary adventures that expand their palates beyond mac-n-cheese and chicken fingers. Each month, kids explore different cuisines at Chicago's best restaurants while interacting with chefs, tasting and rating new dishes, and learning about food preparation and dining etiquette. Meals become memorable experiences as kids discover the world through food.

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Little Diners Crew Culinary Adventures for Kids

2 hoursFree Cancellation

5% savings

from

$105$100

Must-Dos in Chicago

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Chicago's food scene reflects the city's multicultural heritage, creating a unique culinary landscape. Chicago dining experiences offer unique tours that go beyond a simple dinner reservation, to learn more about the Windy City’s foodie heritage. Options range from lunch cruises on Lake Michigan, brunches on the Chicago River, speakeasy tours, pizza crawls, and cooking classes. They’re all designed to leave you well fed and entertained, while you gain a new perspective on the city.

Top Chicago Dining Experiences

11 results

Must-Dos in Chicago

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

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