Chicago vs New York
Chicago or New York? Best season, ideal length of stay, neighbourhoods, dining and where to stay, compared side by side.
Chicago or New York? 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.
New York, United States
The City That Never Sleeps: iconic landmarks, world-class culture, and unparalleled energy.
New York City is an undeniable global epicenter, offering an intoxicating blend of iconic sights, revolutionary art, and culinary innovation. From the dazzling lights of Times Square to the serene expanse of Central Park, every corner holds a new discovery. Immerse yourself in the vibrant energy of this metropolis, a beacon of luxury and limitless possibilities.
- Best time to visit: April-June (spring) or September-October (autumn) for pleasant weather, less humidity, and vibrant outdoor activities. December offers festive holiday charm.
- Ideal length of stay: 5–7 nights
- Currency: United States Dollar ($)
- Getting around: The NYC Subway is the quickest and most efficient way to navigate the city; purchase a MetroCard. Taxis are ubiquitous, but traffic can be heavy. Ride-sharing apps (Uber, Lyft) are also readily available. Walking is excellent for exploring individual neighborhoods, but distances between areas can be significant.
- What to avoid: Don't wait in line for discounted Broadway tickets at TKTS in Times Square; consider booking full-price in advance for premium seats or trying the digital lottery.,Avoid eating at chain restaurants around Times Square; venture into local neighborhoods for authentic cuisine.,Don't forget comfortable walking shoes; you'll be doing a lot of exploring on foot.,Ignoring street performers in subway stations or parks; if you enjoy their act, a small tip is customary.
Where to base yourself in New York
- Manhattan (Midtown): Iconic, bustling, tourist-heavy Best for First-time visitors, theater, major landmarks. Catch a Broadway show.
- Greenwich Village: Bohemian, charming, historic Best for Couples, foodies, live music. Explore Washington Square Park and its surrounding cafes.
- SoHo: Trendy, upscale, artistic Best for Shopping, art galleries, affluent dining. Browse designer boutiques on Greene Street.
- Upper East Side: Elegant, residential, refined Best for Culture, luxury shopping, museum mile. Visit The Metropolitan Museum of Art.
Dining in New York
- Per Se: New American, French Fine Dining. The Chef's Tasting Menu, an unparalleled culinary journey.
- Le Bernardin: French Seafood Fine Dining. The 'Almost Raw', 'Barely Touched', or 'Lightly Cooked' tasting menu.
- Carbone: Italian-American. Spicy Rigatoni Vodka and the Veal Parmesan.
Planning details for New York
- Purchase a CityPASS or a similar attraction pass if you plan to visit multiple major museums and observation decks to save time and money.
- Explore NYC's diverse boroughs beyond Manhattan, like the vibrant street art in Bushwick, Brooklyn, or the culinary delights of Flushing, Queens.
- Catch a sunset view from a less crowded spot like Brooklyn Bridge Park or the High Line, rather than just the Empire State Building.
- Utilize the extensive subway system; it's the fastest way to get around, but avoid rush hour if possible.
How to choose
- Chicago suits travellers who want its particular character
- New York suits travellers who want The City That Never Sleeps: iconic landmarks, world-class culture, and unparalleled energy.
- Both sit in North America; check distance and transport before combining them.
Chicago city guide · New York city guide
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Published by Peters Signature Travel.