Bed and Breakfast in Chicago, IL

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Chicago, IL bed and breakfast
Choose the perfect holiday accommodation
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528 Bed and Breakfasts in Chicago, IL

Best Chicago, IL bed and breakfasts with breakfast included

Dorothy's - Chicago, IL
8.6 130 reviews
Chicago, IL
10/07 – 11/07
SG$364/nightfor 1 night

Dorothy's

1 1
B&B , Chicago
This Lakeview guesthouse is conveniently located less than 1.3km from Lake Michigan, a short walk from Wrigley Field and Briar Street Theatre, and close to the Addison and Belmont Red Line stations.
Offering free continental breakfast, Wi-Fi, and shared kitchen facilities including a fridge, freezer and microwave, this pet-friendly Chicago B&B provides housekeeping services on request and boasts a smoke-free environment.
The Sono Chicago - Chicago, IL
9.7 857 reviews
Chicago, IL
23/07 – 27/07
SG$574/nighttotal: SG$2296 (4 )

The Sono Chicago

1 2
B&B , Chicago
The Sono Chicago guesthouse is located in the Old Town neighbourhood, just a short distance from Lincoln Park Zoo and the Magnificent Mile. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The accommodation features a comfortable bedroom with a private bathroom and a flat-screen TV. Guests can enjoy a complimentary continental breakfast each morning and benefit from free parking, a valuable perk in Chicago.
Ray's Bucktown Bed And Breakfast - Chicago, IL
9.7 703 reviews
Chicago, IL
01/07 – 03/07
SG$372/nighttotal: SG$744 (2 )

Ray's Bucktown Bed And Breakfast

1 1
B&B , Chicago
Ray's Bucktown Bed and Breakfast is located in the Bucktown neighbourhood of Chicago, just a short distance from the Congress Theater, DePaul University, Wrigley Field, and Lincoln Park Zoo. The B&B has excellent user, location, and cleanliness ratings.
Each room in the guesthouse has hardwood floors and a flat-screen TV, while some rooms also have a spa bath. Guests can enjoy a delicious breakfast delivered to their room, relax in the communal areas, or unwind in the sauna after a day exploring the city.
The Publishing House Bed And Breakfast - Chicago, IL
9.7 243 reviews
Chicago, IL
21/09 – 24/09
SG$2134/nighttotal: SG$6402 (3 )

The Publishing House Bed And Breakfast

5 6
B&B , Chicago
The Publishing House Bed and Breakfast is located in Chicago, just a short walk from the United Center and Union Station, with Willis Tower and CIBC Theatre also within easy reach. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The inn features a single bedroom and bathroom, offering a comfortable and intimate stay. Guests can enjoy a range of amenities, including a restaurant, bar, fitness centre, and parking, as well as free Wi-Fi and a shared lounge area.

Best Chicago, IL bed and breakfasts with a garden

Bnb On Grace Street - Modern 2-bedroom Guest Suite - Chicago, IL
9.9 223 reviews
Chicago, IL
01/09 – 05/09
SG$229/nighttotal: SG$916 (4 )

Bnb On Grace Street - Modern 2-bedroom Guest Suite

1 2
B&B , Chicago
This Old Irving Park guesthouse is conveniently located two blocks from the Blue Line 'L' train and Interstate 90, offering easy access to Chicago's city centre and O'Hare International Airport.
The recently renovated two-bedroom suite, sleeping up to five guests, includes a kitchenette with a fridge, freezer, microwave, portable induction stove and electric griddle, a Roku Smart TV, dedicated parking, and a private patio; a Tesla EV charger is also available.
Lyons' Suite - Chicago, IL
8.3 3 reviews
Chicago, IL
24/10 – 01/11
SG$423/nighttotal: SG$3384 (8 )

Lyons' Suite

1 2
B&B , Chicago
This Chicago guesthouse is situated approximately 21 kilometres from Chicago O'Hare International Airport, in a quiet suburban location.
The 46-square-metre property features one bedroom, one bathroom, and can accommodate up to three guests, offering air conditioning, a private terrace, and parking.
Chateau De Woodlawn - Room I - La Tour Eiffel - Chicago, IL
9.1 16 reviews
Chicago, IL
11/08 – 23/08
SG$113/nighttotal: SG$1356 (12 )

Chateau De Woodlawn - Room I - La Tour Eiffel

1 2
B&B , Chicago
Chateau de Woodlawn, a family-friendly guesthouse in Chicago, is conveniently located approximately 5 kilometres from the Museum of Science and Industry and 8.5 kilometres from Guaranteed Rate Field.
This Chicago B&B offers a 15-square-metre room with one bedroom, one bathroom, accommodating up to three guests, and features free Wi-Fi, private parking, a shared kitchen, terrace access, and concierge services.
Amazing Place To Stay Near Downtown Chicago! - Chicago, IL
9.2 7 reviews
Chicago, IL
04/09 – 10/09
SG$184/nighttotal: SG$1104 (6 )

Amazing Place To Stay Near Downtown Chicago!

1 2
B&B , Chicago
This Chicago guesthouse is conveniently located near the city centre, approximately 8 kilometres from Midway International Airport.
The self-catering unit offers one bedroom, one bathroom, free Wi-Fi, air conditioning, and free on-site parking; guests can prepare meals using the fridge and microwave.

Frequently asked questions about bed and breakfast in Chicago, IL

  • What are the must-see sights for first-time visitors on a day trip to Chicago, IL?

    For a day trip, you'd want to hit the main attractions. Start with the iconic Willis Tower, offering stunning views of the city. Then, walk along the Magnificent Mile, a bustling shopping street. Finally, enjoy the stunning architecture of the Chicago Riverwalk, a picturesque waterfront area.
  • What are the best bed and breakfasts in Chicago, IL?

  • In which districts of Chicago, IL should you consider booking a bed and breakfast?

    For a charming bed and breakfast experience, consider the Lincoln Park or Lakeview neighbourhoods. They offer a mix of residential areas, green spaces, and easy access to public transport. You'll find plenty of options in these areas, each with its own unique character.
  • What are the best bed and breakfasts with a pool in Chicago, IL?

  • What dining options are recommended for solo travelers staying at bed and breakfasts in Chicago, IL?

    If you're staying in a bed and breakfast, you'll likely be near some great local restaurants. For a casual and affordable meal, try the iconic Lou Malnati's Pizzeria for Chicago-style deep dish pizza. If you're feeling adventurous, explore the diverse culinary scene in the nearby Wicker Park or Bucktown areas.
  • What are the best bed and breakfasts with a jacuzzi in Chicago, IL?

  • What are the best cultural activities and events in and around Chicago, IL?

    Chicago is a cultural hub! For art lovers, the Art Institute of Chicago is a must-see. The city also hosts numerous festivals throughout the year, including the Chicago Blues Festival and the Taste of Chicago. For a unique experience, visit the Garfield Park Conservatory, a stunning glasshouse showcasing diverse plant life.
  • What are the best bed and breakfasts for families and kids in Chicago, IL?

    The best B&Bs for families and kids in Chicago, IL are Artist Loft - Very Unique, The Greenleaf House and Master Br W/ensuite (600 Sq Ft -) In Chicago Condo.

  • Which hiking trails are recommended for exploring in and around Chicago, IL?

    While Chicago itself is primarily an urban environment, there are great hiking options nearby. The Palos Preserves, about a 45-minute drive from the city, offer scenic trails through forests and prairies. For a shorter hike, explore the trails at the Morton Arboretum, a beautiful botanical garden with diverse plant collections.
  • What are the best pet friendly bed and breakfasts in Chicago, IL?

  • What amenities are commonly offered in bed and breakfasts in Chicago, IL?

    Bed and breakfasts in Chicago typically offer a warm and welcoming atmosphere, with amenities like a hearty breakfast, comfortable rooms, and often a shared living area. Some may also have additional features like a garden or patio, perfect for enjoying a cup of coffee in the morning.
  • What are the best bed and breakfasts with parking in Chicago, IL?

Destinations nearby

Best Chicago, IL bed and breakfasts with parking

Dorothy's - Chicago, IL
Chicago, IL
05/11 – 06/11
SG$611/nightfor 1 night

Dorothy's

1 2
B&B , Chicago
Dorothy's B&B in Chicago is situated 8km from the city centre, near the Ivy League Baseball Club, Our Lady of Mount Carmel Church, and Temple Sholom.
This pet-friendly guesthouse offers free Wi-Fi, on-site parking, and laundry services, providing a peaceful retreat with one bathroom in a quiet residential area.
Beautiful Home Near Downtwon - Free Parking! - Chicago, IL
7.8 9 reviews
Chicago, IL
19/06 – 21/06
SG$269/nighttotal: SG$538 (2 )

Beautiful Home Near Downtwon - Free Parking!

1 2
B&B , Chicago
This Chicago guesthouse is located a short distance from the city centre, approximately 3.5km from Guaranteed Rate Field and 7km from the Museum of Science and Industry.
The 300 square metre property offers one bedroom, one bathroom, and sleeps one guest, featuring a full kitchen, free on-site parking, and free Wi-Fi.
House 5863- Chicago's Premier Bed And Breakfast - Chicago, IL
9.2 631 reviews
Chicago, IL
24/07 – 26/07
SG$432/nighttotal: SG$864 (2 )

House 5863- Chicago's Premier Bed And Breakfast

1 2
B&B , Chicago
Chicago's Premier Bed and Breakfast is situated in the Andersonville neighbourhood, just a short distance from Wrigley Field, Lincoln Park Zoo, and DePaul University. The property consistently receives excellent reviews for its location, cleanliness, and overall experience.
The guesthouse offers a range of modern amenities including a shared kitchen, a terrace, and a garden. Guests can enjoy a continental breakfast, relax in the lounge, or make use of the barbecue facilities.
A Secluded Bedroom With A Private Full Bathroom - Chicago, IL
9.1 20 reviews
Chicago, IL
02/07 – 06/07
SG$216/nighttotal: SG$864 (4 )

A Secluded Bedroom With A Private Full Bathroom

1 2
B&B , Chicago
This Chicago guesthouse is situated in a residential area near 57th Street Beach, approximately 2.4 kilometres from the Museum of Science and Industry.
The 37-square-metre self-catering unit features one bedroom, one bathroom, and accommodates two guests, offering free Wi-Fi, luggage storage, a private garden, and air conditioning.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL bed and breakfasts with air conditioning

Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago, IL
9.8 100 reviews
Chicago, IL
01/07 – 06/07
SG$714/nighttotal: SG$3570 (5 )

Unique Chicago Penthouse Loft - Amazing Deal & Location

1 2
B&B , Chicago
This Roscoe Village guesthouse is located on the north side of Chicago, 2.4 kilometres west of Wrigley Field and near the Paulina Brown Line station.
This 60 square metre penthouse loft offers a private deck, gas fireplace, and chef's kitchen for up to two guests, with a fitness centre available.
Extended Stays In Our Ideal 2 Units In Mag Mile - Chicago, IL
8.6 20 reviews
Chicago, IL
24/12 – 28/12
SG$568/nighttotal: SG$2272 (4 )

Extended Stays In Our Ideal 2 Units In Mag Mile

2 8
B&B , Chicago
This Chicago guesthouse is ideally located on the Magnificent Mile, within easy walking distance of attractions such as the Art Institute of Chicago and Lake Michigan.
Offering two Deluxe Double Queen City View rooms, each spanning 39 square metres, this pet-friendly lodging sleeps up to eight guests and features a 24/7 gym and business centre.
Entire Upstairs In Arts And Crafts Oak Park Home - Chicago, IL
9.8 523 reviews
Chicago, IL
08/10 – 09/10
SG$244/nightfor 1 night

Entire Upstairs In Arts And Crafts Oak Park Home

1 1
B&B , Oak Park
This charming property is situated in a friendly Oak Park neighbourhood, just a short walk from the CTA Blue Line and close to local amenities like coffee shops, restaurants, and parks. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The home has two bedrooms, a futon, and a shared living area, comfortably accommodating up to four guests. Guests can enjoy a private backyard, free on-street parking, and a kitchen with a fridge, microwave, coffee maker, and kettle, perfect for preparing light meals and snacks.
2nd Floor In Law Suite With Separate Entrance. - Chicago, IL
9.6 43 reviews
Chicago, IL
04/08 – 08/08
SG$211/nighttotal: SG$844 (4 )

2nd Floor In Law Suite With Separate Entrance.

1 2
B&B , Chicago
This Portage Park apartment, a short distance from the Jefferson Park Blue Line/Metra station and approximately 16km from O'Hare International Airport, offers convenient access to Chicago's attractions.
The self-contained first-floor unit sleeps two guests, features a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and excellent guest reviews; nearby amenities include Walgreens, Starbucks, Dunkin', and a grocery store.
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