The 20 Best Boutique Hotels in Chicago (2025)

Chicago has a world-class selection of hotels. Its unique architecture — a muddle of sleek skyscrapers and grand historic buildings — provides the perfect base for some truly unique city stays. When it comes to choosing a hotel, our Hotel Gurus always favour a boutique property to get a real flavour of the destination. With this in mind, we have compiled a collection of the best boutique hotels in Chicago chosen on their design, location, service, and amenities. Here you will find something to suit almost all tastes and budgets whether you are looking for a hip destination, cool sophistication or traditional charm. So why not browse through our collection to start planning your next break?

For a historic stay

• The Publishing House is a stylish boutique B&B set in a 110-year-old brick building with a literature theme. Complete with a heaving library and author-themed rooms, this is geek-chic territory. Breakfasts are home-cooked and there is a pantry available for guests all day.
• Set in an iconic Art Deco building downtown, The Pendry Chicago oozes elegance with plush soft furnishings, fireplaces, parquet flooring and views across the city, river and harbour. With a French brasserie and intimate bar for dining and drinks, it's a stylish choice. 

• Large in scale but boutique in style, The Allegro Royal Sonesta Chicago Loop is an elegant pick. Built in 1924, there's an Art-Deco theme throughout, especially in the Gatsby-esque cocktail bar and restaurant. The location is prime theatre-land — the Cadillac Palace Theatre is connected to the property and the Chicago Opera is nearby.
• Art-Deco glamour also reigns supreme at The Gwen, a luxury boutique hotel set in a historic building. Expect jewel tones, gold fittings, glossy marble and amazing city views. The restaurants and a wrap-around rooftop bar are the icing on the cake.

For a B&B

• The Sono is a boutique B&B in the Old Town. Immaculate light-filled rooms are serene yet homely with soft monochrome colour schemes, fluffy carpets and walk-in showers. A dreamy country kitchen with relaxed benches, a rooftop with city views and fireside sitting rooms seal the deal.
• Villa d'Citta is an Italian-themed B&B in a leafy residential neighbourhood. Built in the 1880s, expect high ceilings, wooden pillars and Georgian windows. Spacious suites channel a Mediterranean feel with marble baths, Roman busts and antique beds. Relax by the fire or soak in the outdoor hot tub. Made for couples.
• Harvey House Bed and Breakfast is a small yet sophisticated B&B located in leafy Oak Park. Rooms and suites have been lovingly designed and decorated; expect antique beds, exotic patterned rugs, burning fires and atmospheric slanting ceilings. A cosy hideaway.

For long stays

• Wicker Park Inn offers historic charm combined with boutique style in a residential neighbourhood. The mix of guest rooms and fully functioning apartments can also be booked out exclusively. Decor combines antique fireplaces, exposed brick walls, jewel tones and wallpaper accents. The friendly atmosphere works well for long stays.
• The Guesthouse Hotel comprises a range of fully-equipped one, two and three-bedroom self-catered apartments in the Anderson District. Each of the fresh, lofty and spacious units provides everything expected from a lovely home; dishwashers, driers, gym, balconies and even a roof terrace. A chic option for long stays.

For families

• Freehand is a great value hotel with a boutique feel in downtown Chicago. Rooms are boho chic and come in various sizes including quads and a penthouse, which sleeps up to six, meaning there are flexible options for families. For those of age, there is a popular cocktail bar. With quad rooms available, this is an affordable and hip choice for those travelling with kids.
• Close to beaches and plenty of green space, The Neighbourhood Hotel Lincoln Park  is ideal for families who enjoy the outdoors. Expect stylish, comfy suites with a mix of old and new furnishings; each has its own kitchen and some have a private patio. There are also three-bedroom options, some with cool bunk beds.

For a pool

• The Robey is a modern boutique hotel set in a striking Art-Deco building in Wicker Park. Pick this property for the chic whitewashed rooms (many of which have epic city views) and the French-American restaurant. However, the real lure is the rooftop pool and bar.

For great value

• Claridge House offers boutique luxury for those on a budget. Muted rooms are designed to feel like home with cosy throws, Netflix, spa showers and eclectic artwork. A spa and beautiful French bistro-style bar make this ideal for a romantic and affordable getaway.
• Ruby Room offers contemporary, bold and boutique rooms in Wicker Park. The unique decor mixes patterned curtains and brightly coloured walls with fun vintage-style furniture. Perfect for those who want to experience Chicago daily life without breaking the bank.

• Moxy Chicago Downtown is a fun boutique-style hotel with a reception that doubles as a bar. Decor is contemporary industrial-cool and although the rooms aren't huge they have everything you need. A great base from which to explore the city with a cool vibe and a reasonable price tag.
• Longman & Eagle is a superb farm-to-table restaurant with rooms at reasonable rates. The buzzing dining room channels a traditional Chicago inn with plenty of local charm while the menu is meat-heavy complemented by seasonal cocktails, biodynamic wines and craft beers. Will appeal to those keen to avoid cookie-cutter city hotels.

For proximity to Wrigley Field

• Hotel Zachary is a lively boutique hotel opposite Wrigley Field baseball stadium. An industrial conversion masterclass, interiors are cool, contemporary and yet cosy. Dining spaces are the real draw and popular with locals.

For the Magnificent Mile

• Lively Thompson Chicago is a converted mansion with a fabulous city centre position offering superb Magnificent Mile and lakeside views. Stylish, contemporary, and with an acclaimed Italian restaurant and trendy bar — this well-priced downtown stay is an alluring choice.
• Eurostars Magnificent Mile is well positioned to access the city's best shopping area. Sleek rooms boast floor-to-ceiling windows, polished wood floors, and minimalist furniture. Apogee Terrace is located on the 26th floor — a great place to sip cocktails with the city skyline as a backdrop.
• Another pick close to the Magnificent Mile is Found Hotel Chicago River North with its fun, relaxed atmosphere. Interiors feature mismatched colours, multi-layered textures and ethnic prints, plus there's an Asian-inspired lounge. The shared dormitories offer incredible value for money in prime downtown Chicago.

Still not sure where to book?

• Browse our list of the best places to stay in Chicago.
• Check out all our recommendations in Illinois.
• Refine your search and look at the best hotels in West Loop, Chicago, the best hotels in Downtown Chicago, the best hotels with rooftop pools in Chicago, the best five-star hotels in Chicago, cool hotels in Chicago or the top Chicago Hotels with parking.
• Alternatively, you could contact one of our friendly Gurus for personalised advice.