Photo by Off The Beaten Track

Search B&B in Hillside

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 25 B&B in Hillside with updated reviews, rates, and availability.

The Villa Toscana
Lounge
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (476)
"Absolutely delighted indeed 🙂 So we’d been traveling for a few days as jenn and I had planned. As all new couples experience we were tired, cranky, needed out of the car with each other. I looked to see how close i could get to Wrigley Field a night earlier than I had booked us months in advance. Boom you had me at “Adults Only” and then my love of “old beautiful houses” “warm friendly feeling” “positive vibes” “positive energy” was satisfied at first glimpse of available room. I booked it....
The price is SAR 193
SAR 376 total
includes taxes & fees
30 Sep - 1 Oct
The Villa Toscana
Old Chicago Inn
Property entrance
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, (751)
"Great location. Close to parking garage and train station. Clean room. Adequate breakfast. We stayed in the Wrigleyville - Lakeview area for a concert at the Vic. Was perfect location for the weekend."
Old Chicago Inn
House 5863 - Chicago Bed and Breakfast
Exterior
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (466)
"Had a nice stay. We had a private bath that was down the hall from our room. Everything was clean. Check in was smooth- we communicated through text and that worked well. "
The price is SAR 535
SAR 842 total
includes taxes & fees
24 Sep - 25 Sep
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (319)
"Beautiful and eclectic place. I don’t know who dusts everything but they do a great job. Everything spotless and the staff were wonderful. Will be back!"
The price is SAR 693
SAR 782 total
includes taxes & fees
24 Sep - 25 Sep
Ray's Bucktown B&B
The Sono Chicago
Room
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (429)
"Our first time at a true B & B. I cannot express how much we enjoyed our time at Sono! The friendliness & especially HELPFULNESS of Adie was terrific! We really enjoyed our time in the morning during breakfast with the other guests. We ARE coming back next time we are in Chicago!"
The price is SAR 964
SAR 1,131 total
includes taxes & fees
1 Oct - 2 Oct
The Sono Chicago
The Publishing House B&B
Fireplace
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (157)
"A beautiful B&B in a stunning part of Chicago. So many great restaurants close by and an easy walk to the train. Very accessible to the city. Worth a stay. "
The price is SAR 985
SAR 1,127 total
includes taxes & fees
14 Oct - 15 Oct
The Publishing House B&B
Wicker Park Inn
Room
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (235)
"Very nice option if you want to stay outside of downtown but still in the city. Room was nice and clean, would stay again."
The price is SAR 942
SAR 1,105 total
includes taxes & fees
6 Oct - 7 Oct
Wicker Park Inn
Harvey House Bed & Breakfast
Interior
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (100)
"Great location, restful accommodation with lots of beautiful touches. Very welcoming host with excellent communication. "
The price is SAR 983
SAR 1,091 total
includes taxes & fees
24 Sep - 25 Sep
Harvey House Bed & Breakfast
Villa D' Citta
Front of property
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (92)
"Edith was amazing! She greeted us each morning with coffee, breakfast, and a smile😊 Except the last morning, a woman that introduced herself as the Asst Manager came in while we were eating and complained about the new coffee maker and was pretty unpleasant, but everything and everyone else was excellent!! "
The price is SAR 772
SAR 907 total
includes taxes & fees
15 Oct - 16 Oct
Villa D' Citta
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
9.8 out of 10, Exceptional, (130)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest Room 6
A cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Villa Dubois Guest Room 6
The price is SAR 355
SAR 688 total
includes taxes & fees
25 Sep - 26 Sep
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
A cozy and modern bedroom with brownish paper wall, a comfortable queen size bed, a large window with natural light, and stylish artwork.
Villa Dubois Guest House Room 5
The price is SAR 507
SAR 889 total
includes taxes & fees
29 Sep - 30 Sep
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
A simply furnished room with a plush armchair, a wooden table with and a framed painting on a blue ash paper wall.
Villa Dubois Guest House Room 2
The price is SAR 405
SAR 753 total
includes taxes & fees
26 Sep - 27 Sep
Villa Dubois Guest House Room 2
Dubois Guest House Room 101
Cozy bedroom with a patterned wallpaper wall, a queen sized bed with grey linens, a ceiling fan, a vanity area with a mirror and chair,and a window with white curtains.
Dubois Guest House Room 101
The price is SAR 405
SAR 757 total
includes taxes & fees
24 Sep - 25 Sep
Dubois Guest House Room 101
Dubois Guest House Room 201
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Dubois Guest House Room 201
9.0 out of 10, Wonderful, (2)
The price is SAR 405
SAR 757 total
includes taxes & fees
24 Sep - 25 Sep
Dubois Guest House Room 201
Room in Town house Rogers Park
Living area
Room in Town house Rogers Park
Room in Town house Rogers Park
Dubois Guest House Room 202
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Dubois Guest House Room 202
The price is SAR 405
SAR 757 total
includes taxes & fees
24 Sep - 25 Sep
Dubois Guest House Room 202
Villa Dubois Guest House Room 1
King size bed, grey with blue wall paper design
Villa Dubois Guest House Room 1
The price is SAR 507
SAR 893 total
includes taxes & fees
24 Sep - 25 Sep
Villa Dubois Guest House Room 1
Villa Dubois Guest House Room 4
A cozy and stylish bedroom with a comfortable bed, a patterned armchair, and a unique wall decoration.
Villa Dubois Guest House Room 4
The price is SAR 405
SAR 757 total
includes taxes & fees
24 Sep - 25 Sep
Villa Dubois Guest House Room 4
Dubois Guest House Room 203
Close view of bedroom with a patterned accent wall, a queen size bed with grey linens, a ceiling fan, a vanity area with a mirror and chair, and a window with white curtains.
Dubois Guest House Room 203
The price is SAR 507
SAR 893 total
includes taxes & fees
24 Sep - 25 Sep
Dubois Guest House Room 203
Don't see what you're looking for?
See all available properties in Hillside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Hillside

Sentral Michigan Avenue
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (545)
"Wonderful place "
The price is SAR 634
SAR 855 total
includes taxes & fees
30 Sep - 1 Oct
Sentral Michigan Avenue
Sonder South Wabash
Interior
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (371)
"Great place to stay in the South Loop area. Super nice. Super clean. Super quiet."
The price is SAR 736
SAR 864 total
includes taxes & fees
21 Oct - 22 Oct
Sonder South Wabash
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (161)
"We were really impressed with the location from the green/ pink line. Shopping was a casual 15-20 minutes walk. 2 pubs across the road. Nice safe environment about the location "
The price is SAR 443
SAR 521 total
includes taxes & fees
22 Oct - 23 Oct
Sonder Market Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Hillside?
Whether you’re on a romantic vacation and want to stay somewhere quiet, or you’re traveling solo and hoping to meet fellow tourists, a B&B might be the right choice for your trip. If you’re interested in playing some golf on your trip, Fresh Meadow Golf Club is a good spot to tee off.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to meet guests from other places, and delectable breakfasts, B&Bs offer a unique environment.
What are the top B&Bs in Hillside?
Below are some B&Bs in the area: The Villa Toscana: 9 rooms. 13.8 mi (22.3 km) from the heart of Hillside.Old Chicago Inn: 10 rooms. 13.5 mi (21.7 km) from the downtown core. Enjoy the free full breakfast and fireplace in the lobby. Ray’s Bucktown B&B: 11 rooms. Situated 11.7 mi (18.8 km) from the heart of Hillside. Enjoy the free cooked breakfast and rooftop terrace. House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.4 mi (23.2 km) from the heart of downtown. Enjoy the designer toiletries and private yard. The Sono Chicago: 7 rooms. Located 13.6 mi (21.9 km) from the core of Hillside. Enjoy the rooftop terrace and fireplace in the lobby.
What's the best time of year to stay at a B&B in Hillside?
When you’re dreaming of a trip to Hillside, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Hillside are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Hillside?
Travelers enjoy Hillside for its restaurants and shopping. If you want to check out some popular attractions in Hillside, you might enjoy a visit to Fresh Meadow Golf Club. Wrigley Field and Michigan Avenue are also some sites to visit if you want to see more of the area.
How can I get to and around Hillside?
You can plan your excursions in and around Hillside ahead of time with these transportation options. Fly into Chicago O’Hare Intl. Airport (ORD), which is located 6.9 mi (11 km) away from the heart of the city. You can also search for flights into Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.