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Check prices for these dates

Next weekend
15 May - 17 May
In two weeks
22 May - 24 May
In one month
5 Jun - 7 Jun
In two months
3 Jul - 5 Jul

Our top choices for Chicago bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (508 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is S$193
includes taxes & fees
11 May - 12 May
The Sono Chicago
Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (203 reviews)
"Loved this place - little gem that you'd never notice from the street. Great breakfast and the beds were good too."
United States
Noah
The price is S$430
includes taxes & fees
20 May - 21 May
The Publishing House B&B
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (121 reviews)
"First time at Dorothy's but I've stayed at her sister location so I know the owner/management and what to expect. Great location and the building is kept up very well. My only non happy comment was no dresser in this room. Its ok since this visit was just me. Being able to use a full kitchen and store food in the refrigerator is a major plus"
United States
Robert
The price is S$273
includes taxes & fees
10 May - 11 May
Dorothy's
Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (639 reviews)
"The Villa Toscana is in a great location!"
United States
Sophie
The price is S$157
includes taxes & fees
12 May - 13 May
The Villa Toscana
Front of property

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (502 reviews)
"Great place and neighborhood to stay. Walked everywhere, including to the beach. The room had everything I needed. Fresh coffee and breakfast items steps from my room in the morning. Will stay again. "
United States
Cheryl
The price is S$266
includes taxes & fees
12 May - 13 May
House 5863 - Chicago Bed and Breakfast
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (398 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is S$241
includes taxes & fees
11 May - 12 May
Ray's Bucktown B&B
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (118 reviews)
"Gina and staff were warm and friendly. When our toilet clogged, we got upgraded. When we needed a delayed checkout, they accommodated. We had a fire for a cold night and got delicious eggs and crispy bacon for breakfast. Highly recommend for those lovers of all things Italian. "
United States
Dana
The price is S$392
includes taxes & fees
12 May - 13 May
Villa D' Citta
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (263 reviews)
"Adorable space, comfortable bed, friendly staff"
United States
Marie
The price is S$328
includes taxes & fees
11 May - 12 May
Wicker Park Inn
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (124 reviews)
"The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha."
United States
Timothy
The price is S$368
includes taxes & fees
11 May - 12 May
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"The room was exceptionally clean and the staff was great! The location 1/2 block from Michigan Ave. We had a wonderful stay!"
Danny 3-night trip
Posted 3 hours ago
Hotel Riu Plaza Chicago

Find out more about Chicago

Chicago B&B information

Number of reviews
2,478
Accommodation
9 B&B
Lowest Price
S$157
Highest Price
S$430

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 Sono Chicago: 7 rooms. Enjoy the rooftop terrace and fireplace in reception. The Villa Toscana: 9 rooms. House 5863 - Chicago Bed and Breakfast: 7 rooms. Enjoy the designer toiletries and private garden. 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 14 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 Navy Pier and Naval Base Great Lakes 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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