Boston vs Chicago
Boston or Chicago? Best season, ideal length of stay, neighbourhoods, dining and where to stay, compared side by side.
Boston 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.
Boston, United States
Boston packs nearly four centuries of American history into a compact, walkable city of brick lanes, harbour views and leading universities. Beacon Hill's gas-lit streets, the Back Bay's brownstones and an excellent seafood scene make it an easy and elegant long weekend, especially in late spring and autumn.
- Getting around: Boston is best explored on foot, supplemented by the T subway. Logan Airport is close to downtown: the Silver Line bus, the water taxi or a short car ride all work. Avoid driving in the centre, where streets are narrow and parking is scarce.
- What to avoid: Driving downtown; walking and the T are faster.,Visiting in mid-winter if you dislike snow and cold.,Skipping reservations on autumn weekends, when the city fills with visitors and university events.,Calling it 'Bean Town' to locals.
Where to base yourself in Boston
- Beacon Hill: Gas-lit lanes and Federal-style brick row houses beside the State House and Boston Common. Best for History, antiques shops and a classic Boston setting.. A walk down Acorn Street and along Charles Street's shops.
- Back Bay: Elegant Victorian brownstones, Newbury Street boutiques and Copley Square. Best for Shopping, galleries and central hotels.. Newbury Street's boutiques, then the Boston Public Library's courtyard.
- North End: Boston's Italian quarter, with narrow streets of cafés, bakeries and trattorias. Best for Food, Freedom Trail landmarks and an evening stroll.. Cannoli after dinner on Hanover Street.
- Seaport: A modern waterfront district of restaurants, contemporary hotels and the Institute of Contemporary Art. Best for Harbour views, seafood and newer hotels.. The ICA's harbour-facing galleries at sunset.
Dining in Boston
- Neptune Oyster: Seafood. The hot buttered lobster roll and a selection of raw oysters.
- Mistral: French-Mediterranean. Seasonal French-Mediterranean plates in an elegant South End room.
- Union Oyster House: Traditional New England. Clam chowder and oysters at the raw bar in one of America's oldest restaurants.
Planning details for Boston
- Follow the red-brick Freedom Trail for 2.5 miles of Revolutionary landmarks; walk it in the morning before tour groups.
- Visit the Isabella Stewart Gardner Museum, whose Venetian-style courtyard is a quiet escape.
- Catch a game at Fenway Park, Major League Baseball's oldest ballpark, in season.
- Autumn is peak season; book hotels early for September and October weekends.
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
- Boston 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.
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Published by Peters Signature Travel.