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Browse Select Chicago B&B

The Villa Toscana
Exterior
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (477)
"Absolutely delighted indeed 🙂 So we’d been traveling for a few days as jenn and I had planned. As all new couples experience we were tired, cranky, needed out of the car with each other. I looked to see how close i could get to Wrigley Field a night earlier than I had booked us months in advance. Boom you had me at “Adults Only” and then my love of “old beautiful houses” “warm friendly feeling” “positive vibes” “positive energy” was satisfied at first glimpse of available room. I booked it....
The price is 1.255.227 ₫
2.457.230 ₫ total
includes taxes & fees
30 Sept - 1 Oct
The Villa Toscana
Old Chicago Inn
Fireplace
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, (753)
"The only concern was that no large coffee cups were ever restocked in the 3rd floor kitchen area once they ran out. "
Old Chicago Inn
House 5863 - Chicago Bed and Breakfast
Exterior
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (466)
"This was such a lovely gem of a mini-hotel. Very clean, stylish, and easy to get in and out. Management was very friendly and communicative. "
The price is 3.873.398 ₫
5.974.870 ₫ total
includes taxes & fees
29 Sept - 30 Sept
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (319)
"Beautiful and eclectic place. I don’t know who dusts everything but they do a great job. Everything spotless and the staff were wonderful. Will be back!"
The price is 4.545.467 ₫
5.131.280 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Ray's Bucktown B&B
The Sono Chicago
Private kitchen
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (429)
"Our first time at a true B & B. I cannot express how much we enjoyed our time at Sono! The friendliness & especially HELPFULNESS of Adie was terrific! We really enjoyed our time in the morning during breakfast with the other guests. We ARE coming back next time we are in Chicago!"
The price is 3.895.531 ₫
4.572.822 ₫ total
includes taxes & fees
29 Sept - 30 Sept
The Sono Chicago
The Publishing House B&B
Staircase
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (158)
"A beautiful B&B in a stunning part of Chicago. So many great restaurants close by and an easy walk to the train. Very accessible to the city. Worth a stay. "
The price is 5.444.890 ₫
6.146.737 ₫ total
includes taxes & fees
27 Oct - 28 Oct
The Publishing House B&B
Harvey House Bed & Breakfast
Property entrance
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (100)
"Great location, restful accommodation with lots of beautiful touches. Very welcoming host with excellent communication. "
The price is 6.448.868 ₫
7.157.013 ₫ total
includes taxes & fees
3 Oct - 4 Oct
Harvey House Bed & Breakfast
Wicker Park Inn
Property entrance
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (236)
"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 5.924.454 ₫
6.954.716 ₫ total
includes taxes & fees
9 Oct - 10 Oct
Wicker Park Inn
Villa D' Citta
Lobby sitting area
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (92)
"Edith was amazing! She greeted us each morning with coffee, breakfast, and a smile😊 Except the last morning, a woman that introduced herself as the Asst Manager came in while we were eating and complained about the new coffee maker and was pretty unpleasant, but everything and everyone else was excellent!! "
The price is 5.062.469 ₫
5.942.898 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Villa D' Citta
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Other property types in Chicago

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (546)
"I would absolutely stay here again. "
The price is 3.519.258 ₫
4.852.936 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Sentral Michigan Avenue
Sonder South Wabash
Interior
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (373)
"This was my first time booking a Sonder property for my stay and I must say, this may become my preferred option for accommodations. The apartment was clean and safe. Bedding, furniture etc was in excellent condition. I was pleasantly surprised."
The price is 4.744.801 ₫
5.569.922 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Sonder South Wabash
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (162)
"We were really impressed with the location from the green/ pink line. Shopping was a casual 15-20 minutes walk. 2 pubs across the road. Nice safe environment about the location "
The price is 2.882.914 ₫
3.384.253 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Sonder Market Hall
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.

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 Art Institute of Chicago or Fine Arts Building 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.
How many bed & breakfasts should I expect to find in Chicago?
Expedia has 33 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.