Aspen vs Chicago
Aspen or Chicago? Best season, ideal length of stay, neighbourhoods, dining and where to stay, compared side by side.
Aspen or Chicago? Side-by-side on best time to go, ideal length of stay, neighbourhoods, dining, costs and where to stay — with a clear verdict.
Aspen, United States
Nestled in the majestic Rocky Mountains, Aspen, Colorado, stands as a premier luxury destination, blending world-class outdoor adventure with unparalleled sophistication. This chic mountain town offers an exclusive retreat, where stunning natural beauty meets haute couture, refined dining, and vibrant arts and culture.
- Getting around: For seamless luxury transit, a dedicated chauffeured SUV is ideal for navigating the mountain roads and city. Within downtown, walking is pleasant, and complimentary shuttles connect the four ski mountains. Private jet services into Aspen Pitkin County Airport (ASE) offer an exclusive arrival.
- What to avoid: Underestimating the effects of altitude – hydrate generously and take it easy on arrival.,Attempting to find last-minute dinner reservations at top restaurants during peak season.,Forgetting to pack layers; mountain weather can change rapidly.
Where to base yourself in Aspen
- Downtown Aspen: Luxurious and lively. High-end boutiques, gourmet restaurants, and art galleries set against a stunning mountain backdrop. Best for Shopping, fine dining, après-ski, and celebrity spotting.. An evening stroll past designer shops and illuminated art galleries.
- West End: Historic and residential charm. Victorian homes, quiet streets, and proximity to cultural institutions. Best for Peaceful walks, architecture lovers, and those seeking a quieter stay close to town.. Exploring the historic Victorian homes adorned with intricate details.
- Red Mountain: Exclusivity and panoramic views. Home to multi-million dollar estates and breathtaking vistas of the Elk Mountains. Best for Ultimate privacy, spectacular views, and luxurious residential stays.. Enjoying a private chef experience at your magnificent Red Mountain villa.
- Snowmass Village: Family-friendly luxury with vast ski-in/ski-out access and a vibrant village atmosphere, just a short drive from Aspen. Best for Family ski trips, extensive outdoor activities, and comprehensive resort amenities.. Skiing the diverse terrain directly from your luxurious slopeside accommodation.
Dining in Aspen
- Matsuhisa Aspen: Japanese, Peruvian-inspired. Black Cod with Miso, Yellowtail Jalapeño, or the Chef's Omakase.
- Bosq Aspen: Globally Inspired, Modern. Their tasting menu, which changes seasonally and highlights unique global flavors.
- Clark's Oyster Bar Aspen: Seafood, American. A selection of fresh oysters from their daily rotating list and the Lobster Roll.
Planning details for Aspen
- Secure private ski instructors or guides for an unrivaled and personalized mountain experience.
- Explore the Aspen Art Museum, known for its striking contemporary architecture and thought-provoking exhibitions.
- Consider a private helicopter tour over the Maroon Bells for a truly spectacular and exclusive vantage point.
Chicago, United States
Chicago is America's architecture capital: a skyline of landmark towers rises along the river and Lake Michigan, backed by world-class museums, a celebrated dining scene and the Magnificent Mile's shopping. A luxury stay works best in late spring through early autumn, when the lakefront, rooftop bars and architecture cruises are at their best.
- Getting around: The 'L' trains connect both airports to downtown: the Blue Line serves O'Hare and the Orange Line serves Midway. Downtown is walkable, and taxis and ride-hailing are easy to find. Arrange a car service for airport transfers if you are arriving with luggage at rush hour.
- What to avoid: Visiting in deep winter unless you are prepared for freezing lake winds.,Driving downtown, where parking is expensive and traffic is slow.,Asking for ketchup on a Chicago-style hot dog.,Leaving architecture cruise tickets until the day in summer, when departures sell out.
Where to base yourself in Chicago
- River North & Streeterville: Central and polished, around the Magnificent Mile with flagship stores and many of the city's luxury hotels. Best for Shopping, hotels within walking distance of the lake and the river.. An evening walk along the Chicago Riverwalk.
- The Loop: The historic business district of landmark skyscrapers, theatres and Millennium Park. Best for Architecture, the Art Institute and Millennium Park.. Cloud Gate and the Art Institute of Chicago on the same morning.
- Gold Coast: Elegant tree-lined streets of mansions and brownstones near Oak Street Beach. Best for Boutique shopping on Oak Street and a quieter, residential feel.. Oak Street's designer boutiques, then the lakefront path.
- West Loop & Fulton Market: Former meatpacking warehouses now home to the city's busiest restaurant row. Best for Dining, cocktails and design hotels.. Dinner along Randolph Street's restaurant row.
Dining in Chicago
- Alinea: Progressive tasting menu. The full tasting menu, known for theatrical courses and edible balloons.
- Smyth: Contemporary American tasting menu. The seasonal tasting menu built on produce from the restaurant's partner farm.
- Gibsons Bar & Steakhouse: Steakhouse. A prime steak and an oversized slice of cake to share.
Planning details for Chicago
- Take the Chicago Architecture Center's river cruise early in your trip to understand the skyline.
- Book Art Institute tickets online to skip the line.
- Walk or cycle the Lakefront Trail for the best free views of the city.
- Pack layers, even in summer; the lake can drop temperatures quickly.
How to choose
- Aspen suits travellers who want its particular character
- Chicago suits travellers who want its particular character
- Both sit in North America; check distance and transport before combining them.
Aspen city guide · Chicago city guide
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Published by Peters Signature Travel.