Find the Best Chicago Bed and Breakfast

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Browse Select Chicago B&B

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (548)
"Super cute house! Very detailed directions on check in, super easy excellent neighbourhood!"
The price is £81
includes taxes & fees
1 May - 2 May
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 £196
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, (348)
"Amazing property! Cooked to order breakfast, staff off the charts hospitable and friendly. The whole feel of the space is inviting and calm. My room was a cozy little respite from the city, though in a walkable neighborhood. It was home away from home. Definitely want to return. "
The price is £134
includes taxes & fees
6 May - 7 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, (31)
"It was great for a stay in Boystown"
The price is £85
includes taxes & fees
4 May - 5 May
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 £123
includes taxes & fees
11 May - 12 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 £261
includes taxes & fees
5 May - 6 May
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 £200
includes taxes & fees
4 May - 5 May
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

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 £216
includes taxes & fees
8 May - 9 May
Harvey House Bed & Breakfast
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
The price is £192
includes taxes & fees
1 May - 2 May
Wrigleyville Suites Room 1
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 £215
includes taxes & fees
4 May - 5 May
House 5863 - Chicago Bed and Breakfast
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is £217
includes taxes & fees
2 May - 3 May
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is £183
includes taxes & fees
2 May - 3 May
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is £182
includes taxes & fees
4 May - 5 May
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is £218
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 101
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is £217
includes taxes & fees
2 May - 3 May
Dubois Guest House Room 202
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is £217
includes taxes & fees
2 May - 3 May
Villa Dubois Guest House Room 4
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is £217
includes taxes & fees
2 May - 3 May
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is £252
includes taxes & fees
2 May - 3 May
Dubois Guest House Room 203
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is £192
includes taxes & fees
1 May - 2 May
Wrigleyville Suites Room 3
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is £192
includes taxes & fees
1 May - 2 May
Wrigleyville Suites Room 2
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (737)
"Wonderful stay, beautiful views, spacious and clean!"
The price is £140
includes taxes & fees
1 May - 2 May
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (484)
"Good place"
The price is £100
includes taxes & fees
26 May - 27 May
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is £119
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 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.
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 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 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.