A river with a yellow boat, surrounded by tall buildings and a bridge.

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Chicago bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (183 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is S$156
includes taxes & fees
30 Sept - 1 Oct
Dorothy's
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (555 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
The price is S$339
includes taxes & fees
30 Sept - 1 Oct
The Sono Chicago
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

3. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (518 reviews)
"The city was working on the water, so we were unable to shower for two mornings. I just wish we had been informed ahead of time that there would be little to no water pressure, as we would have made arrangements to shower at our daughter’s place. Other than that the place was really comfortable and we will stay here again."
United States
Lisa
The price is S$267
includes taxes & fees
23 Sept - 24 Sept
House 5863 - Chicago Bed and Breakfast
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (675 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is S$171
includes taxes & fees
27 Sept - 28 Sept
The Villa Toscana
A bathroom with a glass-tiled wall, a sink, and a shower area.

5. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (415 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is S$266
includes taxes & fees
28 Sept - 29 Sept
Ray's Bucktown B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

6. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (125 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is S$377
includes taxes & fees
5 Oct - 6 Oct
Villa D' Citta
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

7. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (216 reviews)
"Gorgeous building inside and out. Beautiful clean rooms. Amazing public spaces. Breakfast was by far one of the best meals of the whole trip."
United States
Mollie
The price is S$439
includes taxes & fees
27 Sept - 28 Sept
The Publishing House B&B
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (283 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is S$475
includes taxes & fees
28 Sept - 29 Sept
Wicker Park Inn
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

9. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is S$415
includes taxes & fees
23 Sept - 24 Sept
Harvey House Bed & Breakfast
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.
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Top Chicago Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Stayed in a junior suite !! Very nice until the A/C broke (97* outside) had to drag all of our stuff back to the lobby just to get another room !! When, they should have come up and given us the key to the new room !! Next (2) days in the the room we had no hot water in the morning to take a shower so the next three days were cold showers in the morning (very annoying). I would love to stay there again but I’m not so sure."
Dawn 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Chicago

Chicago B&B information

Number of reviews
2,246
Accommodation
9 B&B
Lowest Price
S$156
Highest Price
S$475

Frequently asked questions

Searching for B&Bs in Chicago?
If you want to find a place to stay with a small number of rooms and a more personalised environment, a bed and breakfast may be the perfect thing for your trip to Chicago. A trip to Chicago wouldn't be complete without a stop at Fine Arts Building or Art Institute of Chicago if you're someone who could spend hours browsing exhibits.
Are you considering apartments over traditional hotel rooms?
B&Bs all have a unique charm — whether it's a cosy reading space or a sunlit breakfast nook, the small details are what make bed and breakfasts a fun place to get away.
What are the best bed and breakfasts in Chicago?
Why not look at these B&Bs in Chicago: The Sono Chicago: 7 rooms. Enjoy the rooftop terrace and fireplace in reception. The Villa Toscana: 9 rooms. Dorothy's: 7 rooms. House 5863 - Chicago Bed and Breakfast: 7 rooms. Enjoy the designer toiletries and private garden. Ray's Bucktown B&B: 11 rooms. Enjoy the free cooked breakfast and rooftop terrace.
How many bed & breakfasts should I expect to find in Chicago?
Expedia has 13 B&Bs in Chicago, so you'll have plenty of options to maximise comfort and relaxation.
What's the best time of year to book my B&B in Chicago?
When you're planning your stay in Chicago, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Chicago is 1260 mm.
What is there to do in Chicago?
Travellers who want to experience Chicago should visit its popular theatre scene and stunning architecture. If you're looking for some activities to entertain you on your trip, consider visiting Soldier Field and Wrigley Field. You should put Navy Pier and Six Flags Great America on your list if you want to see more of the area.
How can I get to and around Chicago?
Planning your excursions in and around Chicago is easier with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.6 mi (13.9 km) away. You can also search for flights into Chicago O'Hare International Airport (ORD), which is 15.7 mi (25.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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