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Check prices for these dates

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

Browse Select Chicago B&B

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (548)
"Cute, cozy, and quiet. Great location in boys Town on Halsted. Plenty of places to eat within walking distance. Good continental breakfast with juice, bagels, yogurt, muffins and more. Things to know: we stayed in the English Room. It's a small room with a private bath and does not have its own climate control as the room is heated along with the rest of the house. It got very warm in the room and we had to open the window to cool it down, so if you need better temperature control, look...
The price is ₹4,784
₹9,033 total
includes taxes & fees
28 Apr - 29 Apr
The Villa Toscana
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (170)
"Was surprisingly excellent "
The price is ₹19,892
₹22,456 total
includes taxes & fees
26 May - 27 May
The Publishing House B&B
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (346)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is ₹12,285
₹13,869 total
includes taxes & fees
30 Apr - 1 May
Ray's Bucktown B&B
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.0 out of 10, Very good, (30)
"It was great for a stay in Boystown"
The price is ₹3,377
₹6,949 total
includes taxes & fees
28 Apr - 29 Apr
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (452)
"This bed and breakfast was an absolutely breathtaking gem that surpassed every expectation we had, delivering an experience that went well beyond what the photographs could capture. From the moment we arrived, we were struck by the stunning beauty of the place, which seemed to offer everything one could possibly desire in a cozy getaway. The owners were the epitome of hospitality—warm, welcoming, and genuinely sweet—always ready to lend a hand with anything we needed, whether it was local...
The price is ₹15,348
₹18,017 total
includes taxes & fees
4 May - 5 May
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is ₹18,567
₹21,796 total
includes taxes & fees
28 Apr - 29 Apr
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is ₹17,553
₹20,605 total
includes taxes & fees
29 Apr - 30 Apr
Villa D' Citta
Harvey House Bed & Breakfast
Free daily breakfast

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Enjoyed my short stay. Wish I could have spent more time here! Quiet, peaceful, safe, and comfortable. I travel frequently for work and this is by far, one of the best experiences I have had. Thank you Beth!"
The price is ₹19,733
₹21,899 total
includes taxes & fees
28 Apr - 29 Apr
Harvey House Bed & Breakfast
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"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 ₹16,500
₹24,535 total
includes taxes & fees
29 Apr - 30 Apr
House 5863 - Chicago Bed and 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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Other property types in Chicago

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (736)
"it was perfect will stay again"
The price is ₹11,524
₹16,031 total
includes taxes & fees
1 May - 2 May
Sentral Michigan Avenue
Sonder South Wabash
36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (482)
"Good place"
The price is ₹10,751
₹12,620 total
includes taxes & fees
26 May - 27 May
Sonder South Wabash
Sonder Market Hall
City view from property

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (274)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is ₹11,343
₹13,316 total
includes taxes & fees
26 May - 27 May
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 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. Dorothy’s: 7 rooms. Ray’s Bucktown B&B: 11 rooms. Enjoy the free cooked breakfast and rooftop terrace. Wicker Park Inn: 11 rooms. 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 36 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 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.