The Ruby Room, a boutique guesthouse in Chicago's Wicker Park neighbourhood, offers eight king rooms and is conveniently located near Wicker Park's restaurants and bars; proximity to other Chicago attractions requires further research to determine precise distances. This Chicago inn boasts ten bathrooms, accommodating up to sixteen guests, and features a private garden, stylish event spaces, and luxurious marble bathrooms; note the absence of televisions in each of the uniquely designed rooms.
Oak Park, IL
10/07 – 12/07
A$1588/nighttotal: A$3176 (2 )
4 Comfortable Units W/ Fitness Center!
4 14
B&B , Chicago
This guest house is located in Chicago's River North district, offering easy access to the Magnificent Mile for shopping and within 2 kilometres of attractions such as Navy Pier, Willis Tower, and Wrigley Field. This establishment offers 4 bedrooms accommodating up to 16 guests, with each 33 square metre room featuring complimentary toiletries, alongside access to a year-round indoor heated swimming pool, a fitness centre, and daily cleaning services.
Oak Park, IL
10/07 – 12/07
A$1588/nighttotal: A$3176 (2 )
4 Kid-friendly Units Near Shedd Aquarium! Parking!
4 14
B&B , Chicago
This B&B is situated in Chicago's River North district, offering proximity to the Magnificent Mile and Navy Pier, approximately 1.6 kilometres and 0.8 kilometres away respectively. The guest house features four bedrooms, each 33 square metres, with capacity for 16 guests, and provides amenities such as air conditioning, internet, a fitness centre, and discounted parking in January and February 2026.
Oak Park, IL
10/07 – 12/07
A$1558/nighttotal: A$3116 (2 )
Four 1br Suites With Full Kitchens, Pet-friendly!
4 14
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.
9.2 49 reviews
Oak Park, IL
06/09 – 07/09
A$458/nightfor 1 night
The Polo Inn Bridgeport U.s.a.
2 2
B&B , Chicago
Bridgeport Bed and Breakfast is situated just six miles south of Chicago's city centre, close to the White Sox stadium and McCormick Place, making it ideal for both sports fans and business travellers. This guesthouse consistently receives excellent reviews for its cleanliness, location, and overall experience. Each suite features a full-size fridge, flat-screen TV, and fingerprint security locks, providing a comfortable and secure stay. Guests can enjoy a complimentary breakfast at the on-site restaurant, Polo Café, and benefit from free shuttle service to McCormick Place and nearby train stations, as well as free parking.
Oak Park, IL
06/09 – 07/09
A$2125/nightfor 1 night
Pristine Apartment With Free Street Parking
3 2
B&B , Chicago
This B&B is located in Chicago's Humboldt Park district, offering direct access to downtown attractions via the #66 Chicago Avenue bus and proximity to Ukrainian Village nightlife. This renovated, three-bedroom upper-level guesthouse accommodates up to seven guests and features a modern bathroom, kitchen with a fridge and microwave, air conditioning, and free street parking, situated approximately 19-22 kilometres from O'Hare International Airport.
9.9 165 reviews
Oak Park, IL
11/10 – 21/10
A$189/nighttotal: A$1890 (10 )
Eddy Street Upstairs Apartment
1 2
B&B , Chicago
This one-bedroom Chicago apartment is situated in the Portage Park neighbourhood, less than 16km from O'Hare International Airport and roughly 20km from the city centre. The self-contained flat, sleeping up to three guests, offers a queen bed, a queen air mattress, free on-street parking, shared laundry facilities, and is conveniently located near Portage Park with its dog park and multiple bus routes; it’s also 420-friendly (outdoor smoking only).
10 2 reviews
Oak Park, IL
06/09 – 07/09
A$953/nightfor 1 night
Roman’s Guest Suite
1 2
B&B , Northlake
This Melrose Park bed and breakfast is conveniently situated just 8 kilometres from O'Hare International Airport, offering easy access for travellers and a short drive to the Allstate Arena and numerous shopping centres. The spacious suite accommodates up to four guests, featuring a private entrance, a separate bedroom, bathroom, living area with a sleeper sofa, and a cosy seating area, all equipped with air conditioning and internet.
Oak Park, IL
10/07 – 12/07
A$1558/nighttotal: A$3116 (2 )
Four Pet-friendly 1br Suites, Free Airport Shuttle
4 14
B&B , Schiller Park
This charming bed and breakfast is just 3 kilometres from O'Hare International Airport, making it a convenient choice for travellers arriving or departing from the airport. The property is situated in the quiet suburb of Schiller Park, offering a peaceful escape from the hustle and bustle of city life. The guesthouse features four bedrooms and four bathrooms, accommodating up to 16 guests. It offers a range of amenities including a fitness centre, a business centre, and a convenience store.
9.7 702 reviews
Oak Park, IL
28/06 – 05/07
A$601/nighttotal: A$4207 (7 )
Ray's Bucktown Bed And Breakfast
1 5
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.
9.2 631 reviews
Oak Park, IL
11/10 – 21/10
A$331/nighttotal: A$3310 (10 )
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.
9.9 461 reviews
Oak Park, IL
06/09 – 07/09
A$1097/nightfor 1 night
Peaceful Portage Park Apartment
1 2
B&B , Chicago
This Portage Park flat, ideally situated between O'Hare International Airport and Chicago's city centre, is approximately 2km from a park boasting playgrounds, tennis courts, and swimming pools. The two-bedroom, one-bathroom apartment sleeps five, includes a kitchen with fridge, freezer, and microwave, plus a garden, parking, and Wi-Fi; family-friendly amenities such as a high chair and travel cot are available.
Best Oak Park, IL bed and breakfasts with breakfast included
9.8 247 reviews
Oak Park, IL
06/09 – 07/09
A$505/nightfor 1 night
Harvey House Bed & Breakfast
1 2
B&B , Oak Park
Harvey House Bed & Breakfast is situated in Oak Park, a short walk from the CTA Green Line Ridgeland stop and just a 15-minute drive from Chicago city centre. The B&B is highly rated for its excellent location, cleanliness, and overall experience. The guest house has one bedroom and one bathroom, accommodating up to two guests. Harvey House offers a range of amenities, including a private jacuzzi, a relaxing garden, and a delicious hot breakfast each morning.
9.7 857 reviews
Oak Park, IL
17/07 – 27/07
A$592/nighttotal: A$5920 (10 )
The Sono Chicago
1 1
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.
9.3 191 reviews
Oak Park, IL
11/10 – 21/10
A$604/nighttotal: A$6040 (10 )
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.
Best Oak Park, IL bed and breakfasts with a garden
9.9 148 reviews
Oak Park, IL
06/09 – 07/09
A$1054/nightfor 1 night
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.
9.8 100 reviews
Oak Park, IL
17/07 – 27/07
A$668/nighttotal: A$6680 (10 )
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.
9.2 7 reviews
Oak Park, IL
28/06 – 03/07
A$424/nighttotal: A$2120 (5 )
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 Oak Park, IL
What are the must-see sights for first-time visitors on a day trip to Oak Park, IL?
For a first-time visit, you should definitely check out the Frank Lloyd Wright Home and Studio, the Unity Temple, and the Ernest Hemingway Birthplace Museum. You'll get a real feel for the history and architecture of Oak Park.
What are the best bed and breakfasts in Oak Park, IL?
In which districts of Oak Park, IL should you consider booking a bed and breakfast?
The best areas to look for bed and breakfasts are the historic districts, like the Pleasant Home district or the Ridgeland district. You'll be close to many of the main attractions and have a more traditional Oak Park experience.
What are the best bed and breakfasts with a jacuzzi in Oak Park, IL?
What is the typical weather in Oak Park, IL, and how does it affect outdoor plans?
Oak Park has a typical mid-continental climate with hot, humid summers and cold, snowy winters. You'll want to pack accordingly and be prepared for anything! Summer is great for outdoor activities, but winter can make things a bit tricky. You'll find lots of indoor activities to keep you busy in the winter though.
What are the best bed and breakfasts for families and kids in Oak Park, IL?
What are the best cultural activities and events in and around Oak Park, IL?
Oak Park has a vibrant arts scene. You can catch a show at the Oak Park Festival Theatre or visit the Oak Park Art League. The annual Oak Park Festival of the Arts is a great event to attend in the summer.
What are the best pet friendly bed and breakfasts in Oak Park, IL?
Which hiking trails are recommended for exploring in and around Oak Park, IL?
There aren't many hiking trails in Oak Park itself, but you can easily get to the Cook County Forest Preserves, which have many trails for hiking and biking. The trails in the Salt Creek Greenway are popular with both locals and visitors.
What are the best bed and breakfasts with parking in Oak Park, IL?
What amenities are commonly offered in bed and breakfasts in Oak Park, IL?
Most bed and breakfasts in Oak Park offer a continental breakfast, free Wi-Fi, and parking. Some also have additional amenities like a shared lounge or a garden.
Destinations nearby
Best Oak Park, IL bed and breakfasts with parking
9.7 702 reviews
Oak Park, IL
28/06 – 05/07
A$601/nighttotal: A$4207 (7 )
Ray's Bucktown Bed And Breakfast
1 5
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.
9.3 191 reviews
Oak Park, IL
11/10 – 21/10
A$604/nighttotal: A$6040 (10 )
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.
9.7 857 reviews
Oak Park, IL
17/07 – 27/07
A$592/nighttotal: A$5920 (10 )
The Sono Chicago
1 1
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.
9.2 49 reviews
Oak Park, IL
06/09 – 07/09
A$458/nightfor 1 night
The Polo Inn Bridgeport U.s.a.
2 2
B&B , Chicago
Bridgeport Bed and Breakfast is situated just six miles south of Chicago's city centre, close to the White Sox stadium and McCormick Place, making it ideal for both sports fans and business travellers. This guesthouse consistently receives excellent reviews for its cleanliness, location, and overall experience. Each suite features a full-size fridge, flat-screen TV, and fingerprint security locks, providing a comfortable and secure stay. Guests can enjoy a complimentary breakfast at the on-site restaurant, Polo Café, and benefit from free shuttle service to McCormick Place and nearby train stations, as well as free parking.
Best Oak Park, IL bed and breakfasts with air conditioning
Oak Park, IL
10/07 – 12/07
A$1588/nighttotal: A$3176 (2 )
4 Units | River North Location | Parking
4 14
B&B , Chicago
This Chicago bed and breakfast is situated in the River North district, offering convenient access to the Magnificent Mile, located 800 meters away, and Navy Pier, approximately 1.6 kilometers distant. The guest house provides four bedrooms accommodating up to 16 guests, with amenities including air conditioning, internet, a fitness centre, and a heated indoor swimming pool open daily from 10 AM to 10 PM, alongside paid on-site parking.
9.8 521 reviews
Oak Park, IL
06/09 – 07/09
A$974/nightfor 1 night
Cozy, Quiet, Garden Getaway!
1 2
B&B , Chicago
This peaceful garden flat is located in Chicago's North Center/Lincoln Square neighbourhood, a 1.6km walk from the 'L' train and Lincoln Square's amenities. The self-contained apartment, sleeping two guests in one bedroom and one bathroom, features a kitchen with a fridge and microwave, air conditioning, free on-street parking, and a private entrance.
Oak Park, IL
10/07 – 12/07
A$1588/nighttotal: A$3176 (2 )
4 Units | Fitness Center And Sun Deck
4 14
B&B , Chicago
This guest house offers four rooms located in Chicago's River North district, within 800 metres of the Magnificent Mile and Navy Pier, providing easy access to dining and entertainment. With accommodation for up to 16 guests, this B&B features air conditioning, Wi-Fi, a shared indoor heated swimming pool, a fitness centre, and on-site paid parking for £39 per day.