Curator’s statement
With sleek rooms, a rooftop bar and ideal access to everything, Pendry Chicago is the perfect base for your Windy City stay. The lobby is a warm and welcoming space, with comfortable couches, plush seating and an inviting ambiance that encourages you to settle in and relax. It’s the perfect spot to regroup with a coffee, sip a cocktail from the lobby bar, or just soak in the stylish vibe before heading out.
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Day 1: Arrival, deep-dish pizza & historic theater
Lobby at the Pendry
Afternoon: Explore the Magnificent Mile
Unpack, refresh and take a walk along the Magnificent Mile — Chicago’s buzzing avenue of upscale shops, architectural gems and people-watching opportunities.
Dinner: LaBriola
Head to LaBriola, just off Michigan Avenue, for some of Chicago’s best deep-dish pizza. Their crispy, focaccia-like crust is legendary, and the menu has great options for salads, pasta and more if you’re not in a pizza mood.
Evening: Show at the Chicago Theatre
Take a short walk to the Chicago Theatre, a stunning 1920s landmark with a glowing marquee and opulent interiors. Whether it’s live music, stand-up or a play, there’s always something magical on stage here.
Day 2: Private tour, Brownie history & Italian vibes
The famous 'first brownie' at the The Palmer (now Chicago Hilton)
Morning: Private city tour with Chicago Tours
Kick off with a 3-hour private tour through Chicago Tours, complete with a driver and expert guide. Cruise through historic neighborhoods like the Gold Coast, Old Town and Hyde Park while soaking up stories of architecture, culture and Chicago lore.
Afternoon: Brownie break at the Hilton Chicago
Your tour ends with a sweet touch: a drop-off at the Hilton Chicago, where the first brownie was created for the 1893 World’s Fair. Order one in the grand lobby lounge and enjoy the setting — equal parts historic and indulgent.
Dinner: Piccolo Sogno
Dinner tonight is at Piccolo Sogno, a warm and lively Italian restaurant with a lush patio and a “see and be seen” vibe. The handmade pastas and all-Italian wine list make this a fan favorite, especially on weekends.
Evening: Nightcap at Château Carbide
Head back to the Pendry and ride the elevator up to Château Carbide, the hotel’s rooftop bar. Sip a cocktail while enjoying sweeping views of the skyline — the perfect way to end a full day in the city.
Day 3: Art, architecture & an elevated farewell
Medieval Wing at the Chicago Institute of Art
Morning: Stroll Millennium Park to the Art Institute
Start your morning with a walk through Millennium Park. Snap photos at Cloud Gate (“The Bean”), admire the landscape design and enjoy the peaceful green space before heading next door to the museum.
Late morning: The Art Institute of Chicago
Explore the Art Institute of Chicago, home to masterpieces by Monet, Van Gogh, Hopper and more. It’s a can’t-miss cultural stop, and a great spot to take things slow and soak in the city's creative side.
Afternoon: Relax at the hotel
After your museum visit, head back to the Pendry to recharge. Whether that’s a nap, a light bite and coffee at Venteux, The Pendry's French Brasserie or a visit to the fitness center, this is your time to wind down before the grand finale.
Dinner: Maple & Ash
Wrap up your Chicago getaway with dinner at Maple & Ash, a bold and sexy Gold Coast steakhouse. Go classic with a perfectly grilled filet, or let the chef surprise you with their “I Don’t Give a F*@k” multi-course experience. It’s indulgent, stylish, and unforgettable — just like Chicago.
Need to know
Final tips:
Transportation: Ride shares and walking will cover most of the trip. CTA is handy if you’re exploring farther out.
Packing essentials: Good walking shoes, a jacket for breezy lakefront nights and something upscale for dinner at Maple & Ash.
Reservations: Strongly recommended for all restaurants and the private tour.
Travel Advisor
Debra Botta
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