Best B&B Hillside in 2026

Q: What are the top B&Bs in Hillside?

Here are some well-liked B&Bs in the area: Dorothy's : 7 rooms. 13.8 mi (22.3 km) from the heart of Hillside. The Sono Chicago : 7 rooms. 13.6 mi (21.9 km) from the city centre. Enjoy the rooftop terrace and fireplace in reception. House 5863 - Chicago Bed and Breakfast : 7 rooms. Situated 14.4 mi (23.2 km) from the heart of Hillside. Enjoy the designer toiletries and private garden. The Villa Toscana : 9 rooms. 13.9 mi (22.3 km) from the city centre. Wicker Park Inn : 11 rooms. Located 12 mi (19.3 km) from the core of Hillside.

A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Our top choices for Hillside bed & breakfast

1. Harvey House Bed & Breakfast

Oak Park

Mia

₹28,674 total

includes taxes & fees

6 Aug - 7 Aug

2. The Publishing House B&B

Downtown Chicago

Sigfredo

₹24,605 total

includes taxes & fees

30 Aug - 31 Aug

3. The Sono Chicago

Near North Side

Bronwyn

₹21,040 total

includes taxes & fees

10 Aug - 11 Aug

4. Dorothy's

Lakeview

Stephanie

₹11,199 total

includes taxes & fees

10 Aug - 11 Aug

Double Room, Private Bathroom (Venetian) | Terrace/patio

5. The Villa Toscana

Lakeview

Shu-Ting

₹14,229 total

includes taxes & fees

10 Aug - 11 Aug

6. Ray's Bucktown B&B

Bucktown

mary

₹23,257 total

includes taxes & fees

11 Aug - 12 Aug

Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area | 51-inch flat-screen TV with cable channels, TV, Netflix

7. House 5863 - Chicago Bed and Breakfast

Edgewater

"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"

Kimberly

₹20,554 total

includes taxes & fees

10 Aug - 11 Aug

8. Wicker Park Inn

West Town

Maggie

₹33,925 total

includes taxes & fees

31 Aug - 1 Sept

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Top Hillside Hotel Reviews

Fairmont Chicago at Millennium Park

10/10 Excellent

"staff was really nice and helpful from start to finish! The room was really nice and spacious and I love how close the hotel is to everything in downtown"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"The room was clean and the perfect location to watch the river get dyed. Because we were there for St Patricks Day, the elevators were a huge problem to get down from our room so ended up taking the stairs. This is not the hotels fault by any means. There is a small restaurant and bar. We only got drinks from there. The decor was great and we were so comfy in our bed. I would definitely stay here again!!"

Find out more about Hillside

Hillside B&B information

Number of reviews	3,019
Accommodation	9 B&B
Lowest Price	₹11,199
Highest Price	₹33,925

Frequently asked questions

Searching for B&Bs in Hillside?

Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're travelling solo and hoping to get some local recommendations, a B&B might be the right choice for your trip. If you're interested in discovering some top attractions, United Center and Wrigley Field are worth a visit.

How do you know if a B&B is a good option for your stay?

With attentive service, opportunities to socialise with other guests and of course a scrumptious breakfast, B&Bs all have a unique environment.

What are the top B&Bs in Hillside?

Here are some well-liked B&Bs in the area: Dorothy's: 7 rooms. 13.8 mi (22.3 km) from the heart of Hillside. The Sono Chicago: 7 rooms. 13.6 mi (21.9 km) from the city centre. Enjoy the rooftop terrace and fireplace in reception. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 14.4 mi (23.2 km) from the heart of Hillside. Enjoy the designer toiletries and private garden. The Villa Toscana: 9 rooms. 13.9 mi (22.3 km) from the city centre. Wicker Park Inn: 11 rooms. Located 12 mi (19.3 km) from the core of Hillside.

When is the best time to stay at a B&B in Hillside?

When you're dreaming of a escape to Hillside, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.

What is there to do in Hillside?

Travellers enjoy Hillside for its restaurants and shopping. United Center and Wrigley Field 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 International Airport (ORD), which is located 6.9 mi (11 km) from the city centre. Otherwise, you can search for flights to Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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