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.

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.