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Check prices for these dates

Next weekend
13 Feb - 15 Feb
In two weeks
20 Feb - 22 Feb
In one month
6 Mar - 8 Mar
In two months
3 Apr - 5 Apr

Our top choices for Chicago bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (492 reviews)
"Fantastic place! Very clean, kind and welcoming staff, great breakfast, and great location!"
United States
Catie
The price is S$172
includes taxes & fees
11 Feb - 12 Feb
The Sono Chicago
Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (196 reviews)
"Very clean room, friendly staff"
United States
STEVEN
The price is S$238
includes taxes & fees
8 Feb - 9 Feb
The Publishing House B&B
Courtyard

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497 reviews)
"Wonderful room, very good breakfast!"
United States
James
The price is S$236
includes taxes & fees
8 Feb - 9 Feb
House 5863 - Chicago Bed and Breakfast
Living area

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very good, (105 reviews)
"cozy and close to cool places"
United States
Winter Fox
The price is S$97
includes taxes & fees
10 Feb - 11 Feb
Dorothy's
Courtyard

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (114 reviews)
"Great place"
United States
Jeffrey
The price is S$307
includes taxes & fees
9 Feb - 10 Feb
Villa D' Citta
Terrace/patio

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (259 reviews)
"Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so."
United States
Jeffrey
Wicker Park Inn
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (388 reviews)
"We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!"
United States
Kristin
The price is S$219
includes taxes & fees
9 Feb - 10 Feb
Ray's Bucktown B&B
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (122 reviews)
"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 S$326
includes taxes & fees
9 Feb - 10 Feb
Harvey House Bed & Breakfast
Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (629 reviews)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is S$92
includes taxes & fees
11 Feb - 12 Feb
The Villa Toscana
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Everything was amazing, specially the breakfast buffet."
Ehsan 1-night trip
Posted 23 hours ago
Hotel Riu Plaza Chicago

Find out more about Chicago

Chicago B&B information

Number of reviews
2,582
Accommodation
9 B&B
Lowest Price
S$92
Highest Price
S$326

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 Villa Toscana: 9 rooms. 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. Ray's Bucktown B&B: 11 rooms. Enjoy the free cooked breakfast and rooftop terrace.
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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