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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

Browse Select Chicago B&B

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (64)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
The price is ฿2,143
฿3,658 total
includes taxes & fees
7 Sept - 8 Sept
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (591)
"Was a great stay!"
The price is ฿2,116
฿3,791 total
includes taxes & fees
25 Aug - 26 Aug
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (370)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is ฿5,855
฿6,610 total
includes taxes & fees
26 Aug - 27 Aug
Ray's Bucktown B&B
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is ฿7,080
฿7,992 total
includes taxes & fees
7 Sept - 8 Sept
The Publishing House B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (479)
"Everything was taken care of! A wonderful stay. "
The price is ฿3,944
฿6,441 total
includes taxes & fees
24 Aug - 25 Aug
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (468)
"Loved the shared kitchen access! "
The price is ฿5,095
฿5,981 total
includes taxes & fees
26 Aug - 27 Aug
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is ฿8,533
฿9,768 total
includes taxes & fees
2 Sept - 3 Sept
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is ฿9,326
฿10,947 total
includes taxes & fees
27 Aug - 28 Aug
Villa D' Citta
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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Beautiful unique hotel, friendly staff and quiet for people who need to rest!"
Valeria I 3-night trip
Posted 14 hours ago
Palmer House a Hilton Hotel

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: Dorothy's: 7 rooms. The Villa Toscana: 9 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. The Publishing House B&B: 11 rooms. Enjoy the free full breakfast and winery.
How many bed & breakfasts should I expect to find in Chicago?
Expedia has 35 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 Wrigley Field and Soldier Field. You should put Michigan Avenue and Navy Pier 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.