A Local’s Guide: Discover Dining and More in Chicago

The Chopping Block: Unleash your inner chef with cooking class at Chicago’s premier home cooking school.

Koval Distillery: A local distillery specializing in craft spirits like whiskey and gin. Learn more on a behind-the-scenes tour or enjoy cocktails, flights and light bites at the tasting room.

Chicago Cultural Center: A landmark building with free exhibits ranging from art to music. Don’t miss the opportunity to admire the world’s largest Tiffany glass dome. It really is stunning.

Walking Public Art Tour: Right across the street from the cultural center, Cloud Gate (aka the bean) is an iconic sculpture in Chicago’s millennium park. You will also find works by artists such as Picasso and Alexander Calder sprinkled throughout Chicago’s Loop.

Chicago Riverwalk: Stroll down this picturesque riverside walkway anytime of day. Make stops along the way to soak in the views at a riverside winery or tap. (Closed during winter.)

Water Taxi: Experience Chicago from a unique perspective by taking a scenic water taxi ride to Chinatown, where you can indulge in delicious dim sum.

Architecture Tour via River: Learn about Chicago’s beautiful architecture and take in stunning views of Chicago’s skyline while on a river tour. I always enjoy sharing in this activity when my own guests visit.

Art Institute of Chicago: Immerse yourself in art at this world-class museum, featuring some of my personal favorite artists and works.

Lincoln Park Zoo: Pop in to this delightful, and free, destination while exploring Chicago’s lakefront trail by Divvy bike.

Kingston Mines: Dive into the world of blues music at this world-famous club.

The Green Mill: Step back in time at the Green Mill, a historic music and poetry club that may have been frequented by infamous mobsters in a bygone era.

Eat

Girl and the Goat: Owned by Top Chef winner Stephanie Izard, this is the spot I return to time after time. It’s approachable and perfect for any occasion. Fantastic small plates meant for sharing mean you can really explore the menu.

Oriole: There’s a reason it has two Michelin stars. Out of this world small bites jumpstart the tasting menu and leave you craving more. Book the kitchen table for an up-close view of the culinary magic.

Moody Tongue: This unique restaurant pairs its tasting menu with chef-driven beers. It’s the first two Michelin star brewery in the world. If a tasting menu isn’t your style, the bar offers a la carte dining and a famous chocolate German cake.

Cabra: Stephanie Izard strikes again with her Peruvian-inspired rooftop restaurant atop the Hoxton hotel. The ceviche is a must-try for either lunch or dinner.

The Loyalist: Indulge your love of cheeseburgers at this moody pub that offers not one, but two amazing burgers.

Galit: This intimate spot offers a four-course, choose-your-own-adventure menu that is perfect for sharing. With a James Beard award-winning chef at the helm, there was no surprise to its neighbors when it earned its first Michelin star.

HaiSous: A Michelin bib gourmand gem, the Vietnamese cuisine is high-quality at a great value.

Kasama: This modern Filipino restaurant, and another of Chicago’s one Michelin stars, is a bakery by day and a fine dining hotspot by night. Securing a reservation here will surely make your friends jealous.

Jake Melnick’s: Catch your favorite sports game while enjoying the firecracker wings and don’t forget the parmesan tots.

Pequod’s: Skip the chains and hit this off-the-beaten-path spot for the world-famous Chicago deep-dish pizza.

GG’s: Your quest for the best fried chicken sandwich might end here.

Little Goat: Discover bold flavors at Girl & the Goat’s diner, open for breakfast, lunch, and dinner.

Southport Corridor Grocery: A go to spot for locals seeking a casual but tasty breakfast or brunch.

Drink

The Aviary: Prepare to have your cocktail expectations shattered at this award-winning bar, where mixology becomes an art form that engages all your senses.

Kumiko: Immerse yourself in an elevated, Japanese-inspired beverage program paired with delightful bites.

Bordel: For an unforgettable night, gather a group and head to this racy cocktail bar and cabaret. Enjoy live performances while sipping on expertly crafted drinks.

Lazy Bird: Seeking an exceptional ambiance and bartenders who can craft any cocktail you desire? Look no further. This modern speakeasy in the Hoxton hotel is a great stop for pre or post-dinner drinks accompanied by live music.

Berkshire Room: This is my go-to spot in town to enjoy the best old-fashioned.

Up & UP: Intimate and chic lounge with views of the Chicago skyline from the 13th floor of the Robey hotel.

The Redhead Piano Bar: An iconic Chicago piano bar tucked away in the bustling River North neighborhood. 

Sparrow: The perfect dark and moody vibe for a nightcap.