The Best Bed & Breakfast Destinations in Chicago

Chicago offers a number of delightful bed and breakfast destinations, and they just happen to be in real neighborhoods bursting with local activities, from dining and drinking establishments to shopping and theatrical venues. So you don't have to sort through them all--or wind up in a place that's a little too lived-in for your tastes--we narrowed the choices to the very best around town.

01 of 05

Longman & Eagle

Address

2657 N Kedzie Ave, Chicago, IL 60647-1607, USA

Get directions

Phone +1 773-276-7110

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Some of the most nationally acclaimed eateries and cocktail lounges are located in hipster neighborhood of Logan Square, so if you don't want to spend most of your vacation dollars in taxi fare you can book one of the six rooms at this inn. Directly below the small, yet contemporary rooms is the Michelin-starred Longman & Eagle. For more dining and drinking choices, you should head over to the nearby Billy Sunday, Fat Rice, Lost Lake, Lula Cafe, Scofflaw, Webster's Wine Bar.

02 of 05

Roscoe Village Guesthouse

Address

2104 W Roscoe St, Chicago, IL 60618, USA

Get directions

Phone +1 773-633-3567

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Not too far from the Chicago Cubs' Wrigley Field and Southport Corridor is Roscoe Village Guesthouse, which features 18 suites equipped with a Jacuzzi, fireplace, and full kitchen with granite and stainless steel appliances. The guesthouse welcomes one pet up to 50 pounds for an additional fee of $20 per night, plus $100 per stay. Guests traveling with pets must call prior to booking to verify availability of a pet-friendly room.

03 of 05

Ruby Room

The eight guestrooms are set up for a tranquil experience that include luxury sleeping accommodations, access to a 5,000-square-foot fitness facility and a secret garden tucked behind the building. The garden is wrapped in an epée fence and adorned with an antique Argentinean barn door. The rooms aren't equipped with televisions or telephones, but you can use your cell phone and the complimentary WiFi. There are an adjoining spa, salon, healing sanctuary and boutique, which aim to make guests feel as though they're in a special sanctuary. For those venturing out in the neighborhood, Wicker Park is home to a great selection of locally owned restaurants and bars in walking distance. Bangers & Lace, Black Bull, Bordel, Buck's Chicago, Enoteca Roma, Milk & Honey and Mirai Sushi are just several that come to mind.

04 of 05

Welcome Inn Manor

Address

4563 S Michigan Ave, Chicago, IL 60653, USA

Get directions

Phone +1 312-493-2953

Inns & Bed and Breakfasts

4.4

Another turn-of-the-20th century property, Welcome Inn is located in the heart of Bronzeville, which boasts a number of prominent African-American-owned businesses. It's also not too far from President Obama's Hyde Park home. Seven guest rooms range from luxury suites to cozy accommodations, and include amenities such as fireplaces, kitchenettes and lounge areas. There's complimentary breakfast and a free shuttle allows guests to explore the city.

Continue to 5 of 5 below.

05 of 05

Villa D’Citta

Address

2230 N Halsted St, Chicago, IL 60614, USA

Get directions

Phone +1 312-771-0696

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You can expect solid accommodations in this posh, vintage building that's been around since 1887 in Lincoln Park. The eight rooms are Italian inspired, such as the Venetian suite, which includes a queen-size bed, flat-screen TV, private bath, sitting area, and a private terrace with walk-out access to the spa and sun deck. For an extra $25 a day, guests may rent an urban cycle to explore Lincoln Park and surrounding neighborhoods like Old Town and Lakeview. The inn is also walking distance to the area's highly regarded theater district of Royal George Theater and Steppenwolf Theatre‎.