Chicago — Traveler Guide
History comes alive in these extraordinary properties. Each hotel occupies a building with genuine heritage significance — whether a former palace, a converted monastery, an art-deco landmark, or a centuries-old townhouse — sensitively restored with contemporary comforts.
Quick Answer
History comes alive in these extraordinary properties. Each hotel occupies a building with genuine heritage significance — whether a former palace, a converted monastery, an art-deco landmark, or a centuries-old townhouse — sensitively restored with contemporary comforts.
6 hotels reviewed · Price range: $$$, $$ · Last updated March 2026
About This Guide
Chicago offers exceptional options for travellers seeking historic hotels, and we've curated the very best. Each property has been selected for its outstanding facilities, prime location, and the quality of experience it delivers. Leading our list, The Drake Hotel Chicago excels with its exceptional attention to detail and commitment to the historic experience. The Hoxton Chicago offers a compelling alternative with its unique approach and distinctive character. Whether you're a first-time visitor to Chicago or returning for another stay, these hotels represent the gold standard for historic accommodation in the city. Each has been independently evaluated for quality, location, and value.
Insider Tips
Book directly with the hotel for the best rate guarantee and potential upgrades.
Read recent guest reviews for the most up-to-date assessment of facilities.
Consider visiting during shoulder season for better rates and fewer crowds.
Ask the concierge for local recommendations — they know Chicago better than any guidebook.
Our Picks
6 hotels · Updated February 2026
Gold Coast
Chicago's grande dame since 1920, the Drake has hosted every US president from Roosevelt to Obama and remains an irreplaceable part of the city's social fabric. The Palm Court afternoon tea, the Coq d'Or cocktail lounge, and rooms with Lake Michigan views make it a compelling historic alternative to the Mag Mile towers.
Fulton Market
The London boutique chain planted its flag in Chicago's hottest food neighbourhood — the former meatpacking Fulton Market District — with a thoughtfully restored industrial building, an excellent ground-floor brasserie, and rates that undercut comparable properties by 30%. Walking distance from the city's best restaurants including Smyth, Girl & the Goat, and Au Cheval.
Magnificent Mile
Named for Gwendolyn Brooks, Illinois's first Poet Laureate, this Art Deco hotel blends Chicago literary heritage with Marriott's Luxury Collection polish. The gold-leaf lobby ceiling and rooftop bar with Mag Mile views are defining features of this mid-range luxury sweet spot.
River North
A scrappy, irreverent River North boutique beloved by creative travellers for its record player–equipped rooms, a lobby with vintage arcade games, and one of the neighbourhood's best late-night bars in Happy Village. Rates are significantly below the Mag Mile competition while the location is equally convenient.
Fulton Market
The neighbourhood's original creative-class hotel, with rooms featuring local artist commissions, a lobby designed for lingering, and a rooftop with fire pits and a view of the West Loop skyline. The ground-floor restaurant and coffee bar hum with the energy of Chicago's creative and tech communities.
River North
Richard Branson's take on the boutique hotel, set in a magnificent 1928 Mayan Revival skyscraper with rooms reimagined as 'Chambers' featuring a clever dressing room foyer, adjustable climate and lighting, and a fridge stocked at grocery-store prices. The Commons Club restaurant and bar is one of River North's most reliably enjoyable dining rooms.
Keep Exploring
Common Questions
Yes — the best historic hotels preserve architectural character while offering thoroughly modern amenities including high-speed WiFi, premium bedding, and contemporary bathrooms.
Room sizes vary. Some heritage properties have grand suites, while others feature cozier rooms with unique architectural details. Room dimensions are usually listed in the booking description.
More Destinations
Prices and availability change daily. Lock in the best rate by booking early — most of our top picks offer free cancellation.
View All Chicago Hotels