Chicago is so much more than deep-dish pizza and a selfie at The Bean. This insider guide takes you beyond the clichés, into the neighborhoods where locals actually eat, shop, and unwind. From mouth-watering pizzerias and taco joints to skyline parks...
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Local-Approved Eats
Hidden Gems & Seasonal Magic
Shop Small & Chic
Local-Approved Eats
Affordable, authentic restaurants Chicagoans actually visit. No overpriced tourist traps, just seriously good food.
The original deep-dish that started it all. Grab a classic pie or try their thin crust for a local-approved twist on tradition.
Pizzeria Uno
Chicago-style hot dogs and Italian beef sandwiches done right. Fast, fun, and wallet-friendly.
Portillo's & Barnelli's Chicago
Iconic breakfast spot serving fluffy pancakes, fresh donuts, and Milk Duds with every coffee—a Chicago tradition since 1923.
Lou Mitchell's
A cozy Little Italy gem serving classic pasta dishes, wood-fired pizzas, and warm hospitality—perfect for a hearty meal without the touristy markup.
Francesca's on Taylor - Little Italy
Legendary, no-frills taco spot where locals happily wait for fresh tortillas and perfectly seasoned fillings.
Taqueria El Milagro
Hidden Gems & Seasonal Magic
Places locals love that tourists often miss—perfect for quiet moments, culture, and holiday sparkle.
A lush indoor oasis, one of the largest conservatories in the country, and totally free.
Garfield Park Conservatory
A scenic elevated path lined with murals and neighborhood views—great for biking or a crisp fall walk.
The 606
A peaceful lakeshore park offering incredible skyline sunsets without the crowds.
Burnham Park Promontory Point
Legendary jazz club with Capone-era history and top-notch live music.
The Green Mill
In December, State Street transforms into a holiday wonderland with elaborate department store window displays (Macy’s at the historic Marshall Field’s building is a must).
Macy's State Street Holiday Windows
Shop Small & Chic
Skip the big box stores and discover Chicago’s indie boutiques, local markets, and vintage treasures.
A multi-level marketplace packed with local artists, makers, and unique gifts.
Andersonville Galleria
Beloved vintage boutique with carefully curated finds at fair prices.
Knee Deep Vintage
A rotating pop-up featuring handmade goods and artisan crafts—check dates if you’re visiting in fall or winter.
Renegade Craft
Three floors of used books in Wicker Park—an absolute haven for book lovers.
Myopic Books
A dreamy boutique offering stunning floral arrangements and eclectic home décor.
