Chicago — Insider Luxury City Guide

Insider luxury city guide to Chicago — hand-selected hotels, fine dining, cultural highlights, and local secrets for discerning travelers.

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.

• Language tip: English is spoken everywhere. Locals give directions by the lake (east) and the city's grid; most addresses count outward from State and Madison streets.
• 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.

Where to base yourself

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.. Top pick: 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.. Top pick: 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.. Top pick: 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.. Top pick: Dinner along Randolph Street's restaurant row..

Where to eat

• Alinea — Progressive tasting menu
• Smyth — Contemporary American tasting menu
• Gibsons Bar & Steakhouse — Steakhouse
• Lou Malnati's — Chicago deep-dish pizza

Insider tips

• 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.

Suggested itinerary

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