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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Chicago bed & breakfast

Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (486)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is HK$1,018
HK$1,195 total
includes taxes & fees
16 Dec - 17 Dec
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (189)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is HK$1,462
HK$1,651 total
includes taxes & fees
18 Dec - 19 Dec
The Publishing House B&B
Courtyard
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.0 out of 10, Wonderful, (496)
"Nice shared spaces"
United States
Erica
The price is HK$761
HK$1,358 total
includes taxes & fees
4 Jan - 5 Jan 2026
House 5863 - Chicago Bed and Breakfast
Living area
Dorothy's

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very good, (97)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is HK$245
HK$560 total
includes taxes & fees
17 Dec - 18 Dec
Dorothy's
Spa
Ray's Bucktown B&B

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (382)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is HK$1,143
HK$1,291 total
includes taxes & fees
16 Dec - 17 Dec
Ray's Bucktown B&B
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Lobby sitting area
Villa D' Citta

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113)
"Great place"
United States
Jeffrey
The price is HK$1,602
HK$1,881 total
includes taxes & fees
16 Dec - 17 Dec
Villa D' Citta
Terrace/patio
The Villa Toscana

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (627)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is HK$224
HK$575 total
includes taxes & fees
18 Dec - 19 Dec
The Villa Toscana
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (120)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
The price is HK$1,798
HK$1,996 total
includes taxes & fees
18 Dec - 19 Dec
Harvey House Bed & Breakfast
Exterior detail
Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
2.0 star property
Humboldt Park
The price is HK$1,773
HK$2,022 total
includes taxes & fees
13 Jan - 14 Jan 2026
Pristine Apartment with Free Street Parking
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

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Location is near to many parks and easy to go around. breakfast is good. "
Daryle D 3-night trip
Posted 1 day ago
Homewood Suites by Hilton Chicago Downtown South Loop

Find out more about Chicago

Chicago B&B information

Number of reviews
2,543
Accommodation
14 B&B
Lowest Price
HK$560
Highest Price
HK$1,996

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. Ray's Bucktown B&B: 11 rooms. Enjoy the free cooked breakfast and rooftop terrace. 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 15 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.

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