Planning a quick getaway to Chicago? Whether you’re a first-timer or a repeat visitor looking to dig deeper, this Friday-to-Sunday itinerary blends iconic sights with hidden gems, delicious eats, and memorable nightlife. Let’s go.
Where to Stay:
The Hoxton, Chicago – West Loop
Trendy, central, and effortlessly cool. The Hoxton is your chic home base with comfy beds, rooftop vibes, and easy access to some of Chicago’s best restaurants. Plus, it’s a quick ride to most neighborhoods you’ll want to explore.
Friday: Arrival + Riverwalk Vibes
Afternoon: Check-in & Explore
After settling in, head straight to the Chicago Riverwalk. Stroll the water’s edge, sip on a cocktail at City Winery, and soak in that iconic skyline.
Dinner: RPM Italian
Upscale, modern, and celebrity-chef approved. Their truffle garlic bread and housemade pasta are a must. Pro tip: Make a reservation in advance.
Evening Drinks: Three Dots and a Dash
A hidden tiki bar with serious speakeasy energy. Expect colorful cocktails, tropical decor, and an unforgettable vibe.
Saturday: Art, Architecture & Nightlife
Morning: Brunch at Beatrix – Fulton Market
Health-conscious but indulgent (yes, that’s possible), Beatrix nails it. Try the mushroom quinoa burger or lemon pancakes.
Late Morning: Art Institute of Chicago
A world-class museum housing works from Monet to Basquiat. Don’t skip the Thorne Miniature Rooms—they’re weirdly fascinating.
Afternoon: Architecture River Cruise
A must-do, even for locals. Grab a seat on the upper deck and learn how Chicago became the architectural capital of the U.S. Bonus: cocktails on board.
Dinner: Girl & the Goat
Top Chef winner Stephanie Izard’s flagship restaurant. Bold flavors, shareable plates, and West Loop charm. (Reservations are gold—book early!)
Nightcap: Lazy Bird (in the basement of The Hoxton)
Cozy, swanky, and jazz-filled. This cocktail den serves up perfectly crafted drinks in an intimate setting. Ideal for winding down.
Sunday: Chill Day + Local Favorites
Breakfast: Doughnut Vault
Tiny but mighty. These doughnuts are legendary, especially the buttermilk old-fashioned. Grab a coffee and take your breakfast on a stroll through River North.
Midday: Millennium Park & The Bean
Yes, it’s touristy. But also… It’s the Bean. Snap a photo, then relax in the park or check out the nearby Lurie Garden if it’s sunny.
Lunch: Lou Malnati’s (River North)
You can’t leave without trying deep-dish pizza. Lou’s is a classic. Go half ‘n’ half with The Malnati Chicago Classic and a veggie option.
Afternoon: Walk through the Gold Coast
Wander tree-lined streets, admire historic mansions, or pop into 3 Arts Club Café at RH Chicago for a last coffee or glass of rosé under chandeliers.
Evening Flight? Grab a quick bite at Ema
Light Mediterranean fare close to the Loop. Order some hummus, lamb kefta, and a glass of wine before heading out.
Pack List:
- Comfortable sneakers (you’ll be walking a lot!)
- A cute layer for rooftop evenings (Chicago can get breezy)
- Portable charger
- Appetite for carbs, cocktails, and culture
Chicago is one of those cities that somehow balances world-class everything with Midwestern charm. A weekend is just enough to fall in love—and start planning your return. Whether you’re in it for the museums, the pizza, or the perfect skyline sunset, the Windy City won’t let you down.
