Chicago (IL)
Boutique Hotels

Blending hostel vibes with boutique charm, Freehand Chicago offers an eclectic, artistic atmosphere. Its vibrant decor and laid-back ambiance make it a trendy, affordable stay near the Magnificent Mile.

A sleek, modern gem near the Magnificent Mile, Ivy Boutique Hotel offers spacious rooms with minimalist design. Its intimate ambiance and personalized service make for a tranquil, luxurious stay.

With striking, minimalist design and floor-to-ceiling windows, Eurostars offers a stylish, serene escape. Its rooftop bar and city views create an unforgettable, cosmopolitan experience.

Set in the historic Gold Coast, Claridge House offers a cozy, home-like atmosphere with contemporary design. Its relaxed vibe and boutique charm make it a peaceful retreat from the city’s hustle and bustle.

With Art Deco design and historic charm, The Allegro offers a glamorous, retro-inspired stay in the Loop. Its chic interiors and lively atmosphere make for a vibrant, stylish escape.

A blend of contemporary art and luxury, 21c Museum Hotel offers a unique, cultural experience. Its on-site art museum and sleek design make it a sophisticated, creative retreat just off the Magnificent Mile.

Bold, playful design meets modern luxury at Virgin Hotels Chicago. Its vibrant atmosphere and innovative features create a fun, dynamic stay in the heart of the Loop.

With bold, playful decor and a prime location in the Loop, Staypineapple offers a quirky, vibrant stay. Its lively atmosphere and unique touches create a fun, memorable escape in the heart of the city.

A Gold Coast icon, Ambassador Chicago offers classic charm with a modern twist. Its historic architecture and stylish interiors make for an elegant, comfortable stay in one of the city’s most exclusive neighborhoods.

In the heart of River North, Acme Hotel offers tech-savvy design with a playful edge. Its funky decor and lively atmosphere create a trendy, modern escape in the city’s entertainment district.

Located in the historic Hyde Park neighborhood, Sophy blends art, science, and music in its design. Its cozy, artistic ambiance reflects the spirit of the nearby University of Chicago and the city's cultural legacy.

With a prime riverfront location, The Langham offers timeless luxury and contemporary elegance. Its sleek design and world-class service create a refined, peaceful haven amidst the city’s vibrant energy.

In the historic Carbide & Carbon Building, Pendry Chicago offers a blend of Art Deco elegance and modern luxury. Its stylish rooftop bar and chic interiors provide a refined, cosmopolitan retreat.

Set on the iconic Navy Pier, Sable offers sleek, modern design with panoramic views of Lake Michigan. Its waterfront location and sophisticated ambiance create a serene, unforgettable stay.

Nestled in the Gold Coast, Viceroy Chicago offers a blend of historic charm and contemporary luxury. Its rooftop pool and Art Deco-inspired interiors create a chic, sophisticated urban retreat.

Set in the heart of Wicker Park, The Robey occupies a striking Art Deco building. Its minimalist design and rooftop views of the Chicago skyline create a vibrant, modern escape.

A Gold Coast classic, The Talbott offers timeless elegance with modern comfort. Its luxurious rooms and refined service make for a sophisticated, relaxed stay in one of Chicago’s most upscale neighborhoods.

Housed in a historic former office building, Kimpton Gray blends vintage charm with modern sophistication. Its rooftop lounge and chic interiors create a stylish, urban escape in the Loop.

Blending the comforts of home with boutique luxury, The Guesthouse offers spacious suites with fully equipped kitchens. Its relaxed, neighborhood vibe provides a tranquil retreat in Andersonville.

A beacon of luxury in the Gold Coast, Waldorf Astoria offers opulent design with French-inspired elegance. Its lavish rooms and world-class amenities create an indulgent, exclusive retreat.

A celebration of art and science, Hotel EMC2 offers an innovative, tech-savvy stay. Its quirky design and creative touches make it a playful, unique retreat in the heart of Streeterville.

Housed in a historic Venetian Gothic building, this hotel offers a nostalgic journey into Chicago's past. With its grand design and playful modern touches, it’s an eclectic mix of old-world charm and urban energy.

Inspired by the Art Deco movement, The Gwen offers a blend of timeless elegance and modern comfort. Its rooftop terrace and striking design provide a chic, luxurious retreat along the Magnificent Mile.

With sweeping views of Lincoln Park and Lake Michigan, Hotel Lincoln offers a playful, vintage-inspired stay. Its quirky decor and lively rooftop bar make for a fun, unique escape.

With floor-to-ceiling windows overlooking Lake Michigan, Thompson Chicago blends bold design with timeless luxury. Its sleek interiors and personalized service offer a refined, intimate stay in the heart of the city.

Set in a former printing house, this boutique B&B offers an intimate, cozy stay with industrial-chic design. Its personalized service and warm ambiance make for a charming escape in the West Loop.

Tucked away in Lincoln Park, this Italian-inspired bed and breakfast offers an intimate, romantic escape. Its charming, vintage decor and cozy atmosphere create a warm, home-like stay.