Top Illinois Dining Experiences

Take in the Chicago skyline from a vantage point most travelers miss on this brunch cruise. Gaze up at the Willis Tower, the Old Chicago Post Office, the Tribune Tower, and much more as you drift along the Chicago River while listening to light commentary and enjoying a curated menu of brunch favorites.

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.

One of the most unique experiences in Chicago. Immerse yourself in the Roaring Twenties. Step back in time to Prohibition Chicago with da gangsters and da flappers, and your host, Vito Valentino. Great music, great food, great comedy, and a great time, not to mention Vito's bootleg hooch. Give da password at the door, but when you're in, you're in.

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!

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.

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.

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.

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).

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.

Enjoy a private and authentic cooking class and meal in a local Naperville home with your host Nancy. Nancy is one of those warm and wonderful people who make you feel at home as soon as you meet her! This is a perfect experience for anyone looking to connect with local culture over food. Your cooking class takes place in Nancy's open kitchen and lasts about 1.5 hours. Choose between Chicago-style deep dish pizza or fresh, handmade pasta for your main. Learn the tips and techniques of Italian American cooking before enjoying the meal you helped prepare with your warm and hospitable host. Come prepared for a morning or evening of food, laughter and, hopefully, new friendship.

Chef Janet, a seasoned head chef, personal chef and culinary instructor, has served and educated countless food enthusiasts throughout her career. Let Chef Janet's expertise and charisma guide you in mastering the art of dumpling-making. This class takes place at a beautiful local venue known for its warm atmosphere and excellent craft beers. In this session, you'll start by preparing meat dumplings (vegetarian option available) using ingredients like carrots, cabbage, scallions, garlic, ginger and soy. You'll then create a tasty dipping sauce with soy and citrus. The class concludes with steaming or pan-frying your dumplings and enjoying your flavorful creations. What to Expect: - Step-by-step guidance from a talented chef who makes it make sense. - A fun, beginner-friendly class where no one judges your knife skills. - Tasting, laughing and leveling up your kitchen game. - Ideal for: a solo outing, date night, girls’ night or group fun.

Sample three different styles of pizza all in one day: this Chicago tasting tour offers a delicious way to explore. In the evening, meet your guide at the first restaurant, and be sure to come hungry—you’ll sample everything from the city’s iconic deep-dish pizza to Neapolitan and artisan slices. In between, meet the pizza makers and learn more about the Windy City’s culinary history.

This beginner-friendly chocolate class turns a classic confection into an approachable, rewarding skill. Led by Chef Janet, the experience focuses on teaching essential techniques while keeping the atmosphere relaxed and fun. You’ll learn how to temper chocolate correctly, experiment with popular fillings and use molds to create beautifully shaped treats. Chef Janet breaks everything down step by step, making the process easy to follow even if you’ve never worked with chocolate before. With plenty of tasting, hands-on practice and a supportive environment, this Chicago class is ideal for dessert lovers, curious home cooks or anyone looking for a creative night out that ends on a sweet note.

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.

Roll, slice and build your own plant-based sushi in this hands-on class in Chicago. Booked through Classpop!, this interactive cooking class with Chef Natalie introduces you to the fundamentals of sushi making using creative vegetarian ingredients. You’ll begin by preparing fillings and practicing simple knife skills to build confidence before rolling. Next, learn how to assemble and roll two sushi styles, including a smoked “salmon” roll made with lentil-based tofu and a spicy dragon roll with carrot “tuna,” cucumber and avocado. Chef Natalie will guide you step by step to help you achieve clean, well-formed rolls. Finish by preparing a light seaweed salad and enjoy your handmade sushi at the end of class.

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.