Kathleen’s Chicago City Guide

Our Chicago stylist, Kathleen, has selected her favorite dining spots, coffee shops, and shopping destinations, offering you an insider’s look at the Windy City. Use Kathleen's guide to navigate Chicago’s top attractions and experience the city in a whole new way!

SHOPPING

For a unique shopping experience, Nomad in River North is a cute designer boutique that also features an amazing coffee bar. Armitage Street is another fantastic shopping destination, filled with little shops and small boutiques like Art Effects and Clare V. Enjoy a leisurely day exploring these stores, with plenty of lunch and coffee shops along the way. Don't miss Alice & Wonder, a Chicago-specific store just a few streets over.

For designer shopping, head up and down Rush Street, where you'll find both well-known brands and unique storefronts like Anine Bing, Reformation, and COS. This mix of high-end and boutique shops makes it a prime spot for fashion enthusiasts.

DINING

Chicago boasts a vibrant culinary scene, and our stylist Kathleen has handpicked some of her favorite spots to dine. If you're in the Logan Square area, don't miss Lonesome Rose. This casual eatery offers great tacos and margaritas in a beautifully designed space. Right next door, Bang Bang Pie and Biscuits is perfect for dessert or a delicious lunch.

For a night out downtown, head to Arbella in River North for fun drinks and a lively atmosphere. If you're craving homemade pasta and desserts, Torchio Pasta Bar is a small, family-owned gem that won't disappoint. Au Cheval in the West Loop is famous for its burgers, but be prepared for a long wait, as they don't take reservations.

COFFEE

Start your day with a visit to Goddess & the Grocer, where the strawberry matcha is a must-try. Ground Up offers a taste of Greek coffee and delicious spinach and feta hand pies. La Colombe, though not specific to Chicago, consistently serves up some of the best coffee in the city with fun latte specials. Finally, Sawada Coffee is renowned for its dirty chais and military lattes, making it a perfect stop for a caffeine fix.

Kathleen's insider tips will help you discover the best of Chicago, from its diverse dining scene to its charming coffee spots and unique shopping destinations. Whether you're a local or visiting the Windy City, this guide is your key to experiencing Chicago like a true insider.

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