3 Streets that Deserve Your Whole Afternoon
Whether you’re here for the food, the shopping, or the neighborhood vibes, these streets deliver the perfect mix of eats, drinks, and things to do.
1. Randolph Street – AKA “Chicago’s Restaurant Row”
Why go: Famous for its award-winning dining scene, Randolph is a food lover’s dream. Start your day with brunch at HIDE+SEEK, grab a locally brewed beer and hearty bites at Haymarket Pub & Brewery, or satisfy your sweet tooth with cookies from Levain Bakery. In between, sip craft cocktails at a rooftop bar and soak in the vibrant West Loop energy.
Don’t miss: Happy hour oysters, rooftop sunset views, and ending the night with dessert from Jeni’s Ice Cream.
2. Fulton Market – Where Trend Meets Tradition
Why go: Fulton Market blends Chicago’s historic meatpacking past with a fresh wave of coffee shops, acclaimed restaurants, and even a couple of art galleries and design studios. Savor globally inspired small plates at Girl & The Goat, enjoy elevated Asian flavors at Sunda, or indulge in farm-to-table fare at The Publican. It’s the perfect street to wander without a plan—just follow your nose (and your cravings).
Don’t miss: Pop into a gallery, grab an artisanal latte, and people-watch from a sidewalk table.
P.S. Mark your calendar: Fulton Market comes alive September 20–21 with the West Loop Music & Art Fest – two days of live music, art activations, and local vendors. Then on September 25, it’s Beers + Bites, a rooftop evening of local brews, seasonal food, and cozy fall vibes.
3. Madison Row – West Loop Fitness and Fun
Why go: This charming stretch is home to local boutique shops, wellness spots, and some of the West Loop’s tastiest bites. Browse the racks at independent fashion boutiques, unwind with a spa session, then fuel up with Italian classics at Monteverde, hearty comfort food at Ranalli’s, or elevated pub fare at Black Barrel Tavern.
Don’t miss: Cap your afternoon with a glass of wine at a cozy bar or a cold pint on a brewery patio—perfect for soaking up the neighborhood vibe.
P.S. Mark your calendar: On September 6, Madison Row Fest takes over the street with food, shopping, music, and activities for the whole family—your perfect excuse to explore everything the block has to offer.
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