The 7 Best Bed and Breakfasts in Chicago

This handsome 11-room bed and breakfast epitomizes the boutique lifestyle. Just minutes from upmarket West Loop restaurants, the former publishing house (built in 1909) is ideal for a peaceful getaway. Rooms are named after famous writers in a nod to the building’s roots, and include kitschy details such as clawfoot tubs, vintage trunks-turned-footstools and longhorn skulls mounted on dusk-blue walls. Rent out the whole space for a one-of-a-kind event, or just enjoy a long weekend, complete with ricotta pancakes in the morning and wine by the fireplace in the evening.

Perched on a tree-lined street, this inn blends in with the historic landscape of its neighborhood. Owned by a 20-year resident of Wicker Park, the space includes homey touches with fireplaces and bouquets on bedside tables. The nine rooms – elevated by floral feature walls – come complete with complimentary gym access to Wicker Park Fitness, plus a freshly prepared gourmet breakfast. If you’re in town for a few weeks, stay a while in one of the multi-room apartments, which have their own kitchens. It’s just steps from the art galleries and restaurants on Milwaukee Ave and a few train stops away from The Loop.

A gray-stone facade and embellished iron gate characterize this stunning Lincoln Park property built in 1887. Wander through the grotto and up the spiral staircase of the Italian-style villa to catch some sun by the spa, or borrow a bike and head out for a beach day along Lake Michigan. Italian architecture exudes old-world charm in each of the unique rooms, some with their own fireplaces and separate entrances. Enjoy a homemade breakfast, or use the kitchen to whip up your own meal using fresh ingredients from the weekly Lincoln Park farmers’ market. No matter your reason for visiting Chicago, a stay at Villa D’Citta will be a memorable experience.

Recharge with a stay in a house designed by famous architect Frank Lloyd Wright. The Prairie-style home in the Rogers Park neighborhood was built in 1915 and features characteristic aspects of Wright’s signature clean-line aesthetic: a flat roof, geometric patterns and the extensive use of natural materials. Each detail of the restoration has been meticulously logged to stay in line with the original vision. Make sure to visit the Japanese Tea House on the property, a wood-walled den that pays homage to Wright’s experience in Japan and its influence on his later works.

Eat, drink and sleep all in one place at this humble inn situated above a Michelin-star restaurant of the same name. No room is the same – ranging from smaller stripped-back spaces with exposed brick and paint-flecked wood paneling, to generously sized options with hanging terrariums, wall murals and electric-violet bedcovers. All also include a vintage cassette console with mixtapes and complimentary earplugs to lessen the buzz of their often-raucous tavern – don’t leave without a glass of whiskey or craft beer in its saloon-style setting.

Live like a local in the apartment-style rooms of the Guesthouse. Once intended to be a luxury condo building (before the recession prompted a change in direction), this boutique hotel is full of deluxe amenities. The plant-filled rooftop deck is a picture-perfect spot for sundowners, there’s a library lined by a colorful spectrum of books and, if you’re craving some cardio, there is a small gym. Suites range from one-bed rooms with a kitchen and private balcony to family-friendly three-bed rooms. If you fancy breakfast in bed, local restaurant Southport Grocery can deliver – the cupcake pancakes are a great gluten-free option.

Situated on the storied streets of historic Old Town, the Sono Chicago is a welcoming big-city stay. The open-plan living area is bathed in natural light – an idyllic spot to dig into continental breakfast made by the friendly host, or recline with a book in front of the flickering fireplace. Rooms are plush and set with pillowy beds and 55-inch TVs, while you can also upgrade for the added luxury of a balcony. Climb up to the roof deck for 360-degree views and evening tipples around the fire pit.