This Albany Park garden flat is conveniently located near Kimball train station, offering easy access to O'Hare International Airport, Chicago city centre, and Wrigley Field, all within a 24-32 km radius. This self-contained apartment sleeps six guests across two bedrooms and one bathroom, featuring a fully equipped kitchenette, in-unit laundry, keyless entry, and a private garden with free on-street parking.
9.1 20 reviews
Chicago, IL
30/06 – 02/07
SG$226/nighttotal: SG$452 (2 )
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.
Chicago, IL
13/09 – 14/09
SG$1022/nightfor 1 night
Four 1br Suites With Full Kitchens, Pet-friendly!
4 9
B&B , Franklin Park
This bed and breakfast is conveniently located in Franklin Park, Illinois, just 2 kilometres from O'Hare International Airport. The surrounding area offers a mix of residential and commercial properties, providing a peaceful atmosphere while being close to amenities. Each of the four units in this guest house offers 753 square feet of space, comfortably accommodating up to 16 guests. The property features a fitness centre, a business centre, outdoor grills, a convenience store, and a free airport shuttle.
10 2 reviews
Chicago, IL
30/07 – 02/08
SG$2581/nighttotal: SG$7743 (3 )
Relaxing Stay Downtown! 2 Units, Pets Are Allowed!
2 3
B&B , Chicago
This Chicago guesthouse is conveniently located in the downtown area, near the Chicago River, within easy walking distance of numerous restaurants and bars, and approximately 5km from Soldier Field, Wrigley Field, and the United Center. Offering two bedrooms and two bathrooms, this establishment sleeps eight guests and features a fitness centre, valet parking, and daily housekeeping, alongside an on-site American tavern serving Chicago-style cuisine.
9.7 199 reviews
Chicago, IL
16/09 – 20/09
SG$195/nighttotal: SG$780 (4 )
Cozy Space In Lincoln Square
1 2
B&B , Chicago
This cosy Chicago basement flat is situated in the Lincoln Square/Ravenswood neighbourhood, a short distance from the Rockwell Brown Line 'L' station and local bus routes, offering easy access to Lincoln Square's shops and restaurants. The self-contained apartment sleeps two guests in one bedroom and one bathroom, features a garden, parking, and includes amenities such as an electric fireplace, and additional bedding and towels; please note that the property has electricity limitations and potential for noise from upstairs.
9.6 34 reviews
Chicago, IL
11/08 – 12/08
SG$201/nightfor 1 night
Chambre Privée Avec Salles De Bain Partagées
1 2
B&B , Chicago
This Chicago guesthouse is ideally situated in Boystown, Lakeview, offering easy access to Chicago's attractions. The self-catering unit features one bedroom, two bathrooms, sleeping two guests, and includes a shared kitchen, laundry, living room, front garden access, plus free Wi-Fi and breakfast, with discounts available at Big Gay Sal’s Pizza downstairs.
9.0 4 reviews
Chicago, IL
25/07 – 26/07
SG$2628/nightfor 1 night
City Escape! 4 Relaxing Units Near Skydeck Chicago
4 8
B&B , Chicago
This Chicago River North guesthouse offers four en-suite rooms, each measuring 17 square metres, a short distance from the Magnificent Mile, Navy Pier, and Washington Square Park. The establishment provides a 24-hour reception, fitness centre, business centre, and daily housekeeping, accommodating up to eight guests with the option of additional units for larger groups; pets are welcome at an extra cost.
9.9 148 reviews
Chicago, IL
14/09 – 19/09
SG$187/nighttotal: SG$935 (5 )
The Vanderpool House
1 2
B&B , Chicago
This Chicago bungalow, situated two blocks from a major transit hub providing easy access to the city centre, O'Hare International Airport, and the north-western suburbs, offers a convenient base for exploring the city. The self-contained property comprises one bedroom, one bathroom, and can sleep four guests using a queen-size bed, sofa bed and air mattress; amenities include a kitchen with fridge and microwave, private patio, free on-site parking, and is located near theatres, restaurants and art museums.
Chicago, IL
01/09 – 31/10
SG$165/nighttotal: SG$9900 (60 )
Chrissy Place
2 2
B&B , Chicago
Chrissy Place, a guest house in Chicago, is located 5.8 kilometres from the Museum of Science and Industry and 9.9 kilometres from Guaranteed Rate Field, with the Field Museum of Natural History and Adler Planetarium & Astronomy Museum both approximately 12.9 kilometres away. This 100-square-metre B&B offers one bedroom and one bathroom for a maximum of one guest, featuring free Wi-Fi, provided towels and bed linen, and a strict no-parties policy, with a checkout time between 08:00 and 11:00.
9.8 100 reviews
Chicago, IL
16/10 – 18/10
SG$670/nighttotal: SG$1340 (2 )
Unique Chicago Penthouse Loft - Amazing Deal & Location
1 1
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.
Chicago, IL
24/06 – 25/06
SG$645/nightfor 1 night
Suite 506 | Stay One Chicago
1 2
B&B , Chicago
Stay One Chicago is a refined boutique guesthouse located in a central Chicago district, offering convenient access to the city's attractions. This establishment provides one bedroom and one bathroom accommodation for up to two guests, featuring air conditioning, Wi-Fi, a swimming pool, jacuzzi, fitness centre, and seamless self-check-in, with three on-site restaurants and exclusive access to Lifetime fitness and wellness amenities.
10 12 reviews
Chicago, IL
02/08 – 03/08
SG$491/nightfor 1 night
The Robey Hotel Urban King Room
1 2
B&B , Chicago
This Chicago guesthouse is situated in the Wicker Park and Bucktown districts, approximately 8 kilometres from Grant Park and Lollapalooza. The 330 sq ft suite offers a king-size bed, sofa, complimentary Wi-Fi, and access to Cafe Robey's all-day brunch and The Up Room's rooftop bar with city views; it sleeps two guests and includes a swimming pool and parking (USD 49 per night valet parking).
Best Chicago, IL bed and breakfasts with breakfast included
8.8 4262 reviews
Chicago, IL
10/07 – 14/07
SG$968/nighttotal: SG$3872 (4 )
Cambria Hotel Chicago Loop - Theatre District
2 4
hotel , Chicago
The Cambria Hotel Chicago Loop/Theatre District is a 4-star hotel located in the heart of the Chicago Loop Theatre District, just a short walk from State Street and five blocks from Millennium Park. The hotel enjoys a very good user rating, making it a popular choice for travellers. The hotel is housed in the historic Oriental Theatre building, giving it a unique character and a touch of old-world charm. Guests can enjoy a range of amenities, including a fitness centre, a games room, and a restaurant and bar serving local craft beer and fresh, local cuisine.
9.7 243 reviews
Chicago, IL
03/07 – 05/07
SG$579/nighttotal: SG$1158 (2 )
The Publishing House Bed And Breakfast
1 2
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.
9.7 857 reviews
Chicago, IL
03/07 – 06/07
SG$415/nighttotal: SG$1245 (3 )
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.
Chicago, IL
06/07 – 10/07
SG$191/nighttotal: SG$764 (4 )
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.
Best Chicago, IL bed and breakfasts with a garden
9.9 93 reviews
Chicago, IL
24/06 – 28/06
SG$574/nighttotal: SG$2296 (4 )
Classic Den @ U Chicago
1 5
B&B , Chicago
This Hyde Park guesthouse offers convenient access to the University of Chicago campus, situated less than 0.8 km away and within a 24 km radius of downtown Chicago via public transport. The self-contained basement apartment features a queen-size bed, kitchenette with mini-fridge and microwave, full bathroom, smart TV, and outdoor patio access; laundry facilities are available on request.
9.5 213 reviews
Chicago, IL
02/07 – 06/07
SG$175/nighttotal: SG$700 (4 )
Alewyfe Farm Urban Garden Oasis- Free Parking!
1 2
B&B , Chicago
This Bohemian Garden Apartment is located in a bohemian neighbourhood in Chicago, two blocks from the Pink Line CTA, Lagunitas Brewery, and Cinespace Film Studios, offering a view of Douglas Park and just 5.6 kilometres from the Loop. The apartment, situated on the first floor of an 1880s brick cottage, features a private bathroom, private entrances, multiple fans, a small window AC for hot days, and a stocked pantry and coffee/tea bar, with a permaculture garden with chickens, a fire pit, and a BBQ available for guests to enjoy.
9.9 406 reviews
Chicago, IL
25/11 – 29/11
SG$136/nighttotal: SG$544 (4 )
Gorgeous, Cozy 1-bedroom Suite In Andersonville
1 2
B&B , Chicago
This Chicago private suite is situated in Andersonville, approximately 1.6 km from Lake Michigan and 8 km north of Chicago's city centre, close to Andersonville's shops and restaurants. The self-contained apartment offers a kitchenette with microwave, fridge, and toaster, sleeps two guests, includes a private entrance and coded lock, and features a shared garden with seating.
9.8 180 reviews
Chicago, IL
07/08 – 09/08
SG$204/nighttotal: SG$408 (2 )
Cozy Suite
1 2
B&B , Oak Park
This charming bed and breakfast is located in a peaceful neighbourhood in Oak Park, just a short walk from restaurants, bars, and shops, and within easy reach of the Green and Blue lines for exploring Chicago. The property has received excellent ratings for cleanliness, location, and overall experience. The guest house offers a spacious private room with a kitchen, deck, and gym, perfect for a single traveller. Guests can enjoy a comfortable and private stay with access to a range of amenities, including a well-equipped kitchen, a relaxing deck, and a fitness centre.
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?
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?
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.
8.3 22 reviews
Chicago, IL
20/08 – 23/08
SG$129/nighttotal: SG$387 (3 )
Afrique Francaise De Woodlawn 1
1 2
B&B , Chicago
Afrique Francaise de Woodlawn 1, a guesthouse in Chicago's Woodlawn neighbourhood, is situated 4 km from the Museum of Science and Industry and 8.4 km from Guaranteed Rate Field, offering easy access to these attractions and a glimpse into the area's history. This 100 square metre self-catering property features one bedroom, one bathroom, sleeps two guests, and includes a private garden, terrace, parking, and a shared kitchen.
9.3 191 reviews
Chicago, IL
03/09 – 07/09
SG$622/nighttotal: SG$2488 (4 )
Villa D' Citta
1 2
B&B , Chicago
This charming bed and breakfast is situated in the heart of Chicago's Lincoln Park, a short walk from the zoo and just a few miles from the Magnificent Mile. It has consistently received excellent ratings for its location, cleanliness and overall experience. The guest rooms are beautifully decorated with an Italian-inspired theme and offer views of the neighbourhood. Guests can enjoy a range of amenities including a private grotto and garden with BBQ facilities, a hot tub, a gourmet kitchen and daily continental breakfast, plus a hot breakfast on weekends.
10 25 reviews
Chicago, IL
10/08 – 13/08
SG$561/nighttotal: SG$1683 (3 )
Wrigleyville Inn
1 3
B&B , Chicago
This bed and breakfast is situated in the Lakeview neighbourhood of Chicago, just a short walk from Wrigley Field and Lake Michigan, offering easy access to the city's attractions and entertainment. The accommodation has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere. The guesthouse features a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as a terrace, a jacuzzi, and parking. Guests can enjoy free Wi-Fi in public areas and weekly housekeeping, making their stay as comfortable and convenient as possible.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL bed and breakfasts with air conditioning
10 1 review
Chicago, IL
17/07 – 18/07
SG$875/nightfor 1 night
Suite 505 | Stay One Chicago
1 2
B&B , Chicago
Stay One Chicago offers a refined boutique hotel experience in a central Chicago district, with self check-in and dedicated workspaces. This establishment provides exclusive access to Lifetime fitness and wellness amenities, alongside three on-site restaurants for curated dining, and boasts one bedroom and one bathroom to accommodate up to two guests.
9.5 26 reviews
Chicago, IL
23/06 – 23/07
SG$80/nighttotal: SG$2400 (30 )
Portage Park - Private Bedroom #2 W/ Shared Spaces
1 1
B&B , Chicago
This Chicago guest house is conveniently located approximately 32km from O'Hare International Airport and downtown Chicago, offering easy access to public transport with a bus stop (number 152 Addison St) just one block away. The modernly renovated garden unit sleeps two guests in one bedroom with one bathroom, and features a well-equipped kitchen with a fridge, freezer, and microwave, plus a smart TV and complimentary street parking.
9.8 551 reviews
Chicago, IL
15/08 – 16/08
SG$140/nightfor 1 night
Lower Level Suite With Private Br And Entrance
1 1
B&B , Hickory Hills
This B&B is located in Hickory Hills, just a short distance from City Hall, offering a peaceful setting away from the hustle and bustle of the downtown area. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The accommodation provides a private lower level with a separate suite, bathroom, garage, and laundry room, comfortably accommodating up to three guests. Guests can enjoy amenities like a small kitchenette, Netflix, and secure parking, alongside the convenience of self check-in and the option to interact with the friendly hosts.
9.9 417 reviews
Chicago, IL
28/07 – 31/07
SG$337/nighttotal: SG$1011 (3 )
Luxe, Private Suite W/own Entrance-2023 Renovated
1 2
B&B , Chicago
This Bucktown studio apartment is ideally located in a quiet residential area, within easy walking distance of Damen Avenue's shops and restaurants, and approximately 3km from Wrigley Field and Lincoln Park. The self-contained unit, sleeping up to two guests, boasts a newly remodelled ensuite bathroom with underfloor heating, a private keyed courtyard, and free on-street parking – a rare find in Chicago's city centre.
