Chicago vs Florence
Chicago or Florence? Best season, ideal length of stay, neighbourhoods, dining and where to stay, compared side by side.
Chicago or Florence? Side-by-side on best time to go, ideal length of stay, neighbourhoods, dining, costs and where to stay — with a clear verdict.
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.
Florence, Italy
Florence, the cradle of the Renaissance, beckons with its unparalleled artistic heritage, exquisite Tuscan cuisine, and timeless beauty. Every corner reveals masterworks by Michelangelo, Botticelli, and Leonardo da Vinci, creating an immersive experience in art and culture. Discover a city where luxury intertwines with history, offering a refined journey for the discerning traveler.
- Getting around: Walking is delightful in Florence's compact historic center, but for convenience and luxury, a chauffeured Mercedes-Benz or private car service is ideal for transfers to and from the airport, visits to hillside viewpoints, or day trips into the Tuscan countryside. Consider a private gondola-style boat tour on the Arno for a unique perspective of the city.
- What to avoid: Queuing for major attractions; always book skip-the-line tickets or private tours well in advance.,Eating at restaurants directly adjacent to the Duomo or Ponte Vecchio, which are often overpriced and tourist-focused.,Visiting the busiest streets in the height of summer midday, when crowds and heat can be overwhelming; plan for early mornings or evenings.
Where to base yourself in Florence
- Oltrarno: Artisan, bohemian, and authentic with numerous workshops and studios. Best for Handicraft shopping, traditional trattorias, and a more local feel.. Exploring the artisan workshops along Via de' Serragli and Via del Presto di San Martino.
- Duomo & Piazza della Signoria: Iconic, bustling, and the heart of Florence's historical and artistic core. Best for Access to major landmarks, high-end shopping, and vibrant city life.. Climbing to the top of Brunelleschi's Dome for unparalleled city views.
- Santo Spirito: Lively, bohemian, and charming with a beautiful piazza and local markets. Best for Local nightlife, authentic Florentine dining, and less touristy experience.. Visiting the basilica and enjoying an aperitivo in Piazza Santo Spirito.
- San Niccolò: Picturesque, upscale, and tranquil, with stunning views of the Arno. Best for Romantic strolls, boutique hotels, and access to panoramic viewpoints.. Walking up to Piazzale Michelangelo for a sunset panorama of Florence.
Dining in Florence
- Enoteca Pinchiorri: 3-Michelin star Modern Tuscan. The extensive tasting menu, perfectly paired with selections from their legendary wine cellar.
- Borgo San Jacopo: 1-Michelin star Creative Tuscan. The 'risotto with cacio e pepe and red prawns' or any dish featuring local seasonal ingredients.
- Ora d'Aria: 1-Michelin star Contemporary Tuscan. Their inventive interpretation of classic Florentine dishes, particularly the pigeon or guinea fowl.
Planning details for Florence
- Arrange a private, after-hours tour of the Uffizi Gallery or Accademia to admire the masterpieces, including Michelangelo's David, in sublime solitude.
- Indulge in a private leather-making workshop with a master artisan in the Oltrarno district, creating a bespoke piece to take home.
- Engage a personal shopper for a curated experience discovering Florence's high fashion, artisanal jewelry, and bespoke tailoring.
How to choose
- Chicago suits travellers who want its particular character
- Florence suits travellers who want its particular character
- They sit in different regions, so most travellers pick one per trip.
Chicago city guide · Florence city guide
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Published by Peters Signature Travel.