🛍️ Eat, Shop, Stay – A Stylish 48 Hours in Chicago’s Gold Coast & River North

From luxury flagships to hidden wine bars, classic steakhouse glamour to rooftop cocktail culture, Chicago’s Gold Coast and River North neighborhoods offer a design-forward escape for travelers who crave walkability, style, and substance. This 48-hour curated itinerary blends high-end shopping, architecture, art, and some of the city’s most unforgettable dining experiences.

✨ Day 1: Boutique Strolls & Rooftop Vibes in the Gold Coast

9:00 AM – Coffee at 3 Arts Club Café at RH Chicago (Gold Coast)

Located inside the stunning Restoration Hardware gallery, this café is a local favorite for a morning coffee surrounded by chandeliers, fountains, and lush greenery under a glass atrium.

Why it works: It’s stylish, serene, and walkable from Oak Street—perfect for setting a chic tone for the day.

Recommended order: A cappuccino and warm maple-glazed donut, or a light avocado toast if you’re staying for breakfast.

10:00 AM – Walk & Shop Oak Street

This tree-lined luxury retail corridor is Chicago’s answer to Rodeo Drive. Browse designer staples like Prada, Dior, and Hermès, then slip into Ikram—a fashion-forward boutique/gallery hybrid showcasing emerging designers.

🛍️ Insider Tip: Stop into Space 519—part concept store, part café—for curated home goods, clean beauty, and lunch-worthy toasts.

12:30 PM – Lunch at Le Colonial

Step back in time at this sophisticated French-Vietnamese spot on Oak Street. The upstairs terrace is the Gold Coast’s hidden gem. Order the crispy chicken dumplings and the shaken beef.

2:00 PM – Architecture Walk or Beach Break

Walk off lunch with a stroll through the nearby Astor Street Historic District, filled with 19th-century mansions and leafy lanes. Or, dip your toes into Oak Street Beach, just a block from the shopping strip.

4:00 PM – Check In: The Peninsula Chicago

This iconic five-star stay balances classic elegance with modern amenities. Book a suite for skyline views and plan a visit to the rooftop spa.

🧖 Pro Tip: Reserve a late massage at the Peninsula Spa, then head straight to the indoor pool for peak relaxation.

6:30 PM – Dinner at Adalina

Italian glamour meets bold flavors at this modern fine-dining spot. Start with whipped ricotta and end with house-made pasta or a Tomahawk for two.

9:00 PM – Drinks at The J. Parker

Head to this rooftop lounge atop the Lincoln Hotel (a quick rideshare away) for cocktails with panoramic city and lake views. The Gold Coast skyline shimmers from this perfect nightcap perch.

🎨 Day 2: Design, Galleries & Culinary Gems in River North

8:30 AM – Breakfast at Beatrix – River North

This bright and modern café is beloved for fresh-squeezed juices, healthy breakfast bowls, and bakery treats. Grab a table near the window and fuel up.

10:00 AM – Gallery Hopping on Superior Street

River North is home to Chicago’s largest gallery district. Walk Superior, Franklin, and Wells Streets to explore contemporary galleries like Zolla/Lieberman, Addington Gallery, and Jean Albano Gallery. You’ll find everything from abstract sculpture to experimental photography.

12:30 PM – Lunch at Ema

This light-filled Mediterranean spot from Chef CJ Jacobson serves shareable spreads, house-made labneh, and spicy lamb kefta in a stylish, coastal-inspired setting.

🍸 Try the cucumber gin cooler for a refreshing midday sip.

2:00 PM – Check In: The Gwen, a Luxury Collection Hotel

Tucked inside the McGraw-Hill building off Michigan Avenue, The Gwen oozes Art Deco glamour with sleek, contemporary interiors and a fantastic terrace lounge.

3:00 PM – Shopping at The Shops at North Bridge

Walkable from your hotel, this mix of luxury and accessible retailers includes Nordstrom’s flagship, Sephora, and emerging local labels. For vintage, swing by Lost Girls Vintage in nearby West Town later in the day.

5:30 PM – Happy Hour at RPM Seafood

Riverside views and expertly crafted cocktails make this an essential early evening stop. Share oysters and a crudo sampler as the river turns gold with sunset.

7:30 PM – Dinner at Siena Tavern

A buzzy River North staple known for truffle pasta, wood-fired pizzas, and bold Italian flavors in a dimly lit, velvet-heavy dining room.

10:00 PM – Drinks & DJ Sets at Celeste

Finish your night at this multi-level cocktail lounge-meets-nightclub in River North. The garden rooftop is intimate and eclectic, while the Deco-style main floor offers mood lighting and strong drinks.

🛏️ Where to Stay: Top Picks by Neighborhood

Gold Coast:

• The Peninsula Chicago – Iconic luxury, rooftop spa, impeccable service
• Viceroy Chicago – Boutique elegance meets bold design in a historic building
• Thompson Chicago – Sophisticated, modern interiors with Lake Michigan views

River North:

• The Gwen – Art Deco flair with terrace bar and designer interiors
• 21c Museum Hotel – Boutique-meets-gallery, rotating exhibitions and stylish rooms
• Trump International Hotel & Tower Chicago – Luxe amenities, spa, and riverside location

✨ Final Vibes

If your perfect weekend includes statement shopping, gallery gazing, rooftop sipping, and well-curated spaces, then Chicago’s Gold Coast and River North offer a perfectly packaged urban escape. Chic yet approachable, classic but never dated—these neighborhoods remind you why Chicago is one of America’s most stylish cities.

🏞️ Find your perfect waterfront getaway with Lakeside Escapes: Chicago’s Best Lake Destinations. From peaceful retreats to vibrant beaches, this guide shows you where to relax, recharge, and soak in the lakefront beauty.