Search Bed and Breakfast in Chicago

  • 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

Featured B&B in Chicago

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (503)
"Complimentary breakfast was far beyond "continental", it was handmade from scratch and incredible! That's what really stood out. Otherwise my stay was also great, everything the listing claimed to be."
The price is S$93
includes taxes & fees
4 Dec - 5 Dec
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, (333)
"We were a last minute stay, and staff took extra care to make sure our arrival went smoothly. Breakfast was excellent - lots of choices, all delicious "
The price is S$233
includes taxes & fees
10 Dec - 11 Dec
Ray's Bucktown 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, (470)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is S$290
includes taxes & fees
4 Dec - 5 Dec
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (238)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is S$325
includes taxes & fees
15 Dec - 16 Dec
Wicker Park Inn
Old Chicago Inn
Fireplace

Old Chicago Inn

2.0 star property
7.4 out of 10, Good, (763)
"Wonderful alternative to usual hotel properties at comparable prices. "
Old Chicago Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (436)
"The Sono Chicago was a dream! Staff & Owner were friendly, accommodating, and gave great advice for dining & entertainment. Our bed was comfortable, bathroom was luxurious, and the balcony was fun for morning coffee. There is a nice rooftop area with seating and fire tables where you can relax/socialize. Parking was convenient and FREE! I def recommend The Sono Chicago!"
The price is S$207
includes taxes & fees
4 Dec - 5 Dec
The Sono Chicago
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
9.0 out of 10, Wonderful, (2)
"Quaint, convenient, and extremely friendly. Recommending it to all my friends traveling to Chicago. "
The price is S$90
includes taxes & fees
4 Dec - 5 Dec
Dorothy's
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (98)
"Perfection "
The price is S$360
includes taxes & fees
9 Dec - 10 Dec
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (106)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is S$343
includes taxes & fees
9 Dec - 10 Dec
Harvey House Bed & Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (161)
"This was the nicest stay I have had in years. Felt like a weekend with your best friend and they are an excellent host. Every amenity and design of the place is well intentioned and thought out. I will definitely be back!"
The price is S$233
includes taxes & fees
15 Dec - 16 Dec
The Publishing House B&B
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.
Don't see what you're looking for?
See all available properties in Chicago
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 Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (607)
"This is an apartment unit for rent. It had a full kitchen and nice bathroom. The room was clean and the bed was soft. It has directv and the staff was nice. Parking was good but you have to walk around the corner to come inside and it was more inconvenient than just walking in after parking."
The price is S$209
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (216)
"I love everything about Sonder hotels! Great location to catch the subway. We were able to park on the street with no issues. My only complaint was that we were on the second floor and one night the nightclub below was so loud that it seemed like the whole room was thumping! So beware if you book Thursday, Friday, Saturday! "
The price is S$127
includes taxes & fees
24 Dec - 25 Dec
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (401)
"The location was perfect: close to grocery, public transportation and expressways. Unfortunately there is only street parking available, but I knew this when I booked. Had trouble getting in the front door which was VERY frustrating, but was able to speak to an agent easily. It did take them a while to remedy., and they gave a small credit for that. The layout of the 2 bedroom was nice; the furniture was what you might expect in a mid-range hotel: we had to put bed pillows on the sofa for...
The price is S$232
includes taxes & fees
8 Dec - 9 Dec
Sonder South Wabash
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 Villa Toscana: 9 rooms. Old Chicago Inn: 10 rooms. Enjoy the free full breakfast and fireplace in reception. Ray’s Bucktown B&B: 11 rooms. Enjoy the free cooked breakfast and rooftop terrace. House 5863 - Chicago Bed and Breakfast: 7 rooms. Enjoy the designer toiletries and private garden. The Sono Chicago: 7 rooms. Enjoy the rooftop terrace and fireplace in reception.
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 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.