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Chicago bed & breakfasts

Search hundreds of travel sites at once for Bed & Breakfasts in Chicago

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Best Chicago bed & breakfasts

Most recommended Chicago bed & breakfasts

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The Villa Toscana - Chicago - Living room
The Villa Toscana
7.6 Good
Lake View₪630+
₪630+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Ray's Bucktown Bed And Breakfast
9.6 Wonderful
₪1,057+
₪1,057+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Villa D' Citta - Chicago - Dining room
Villa D' Citta - Chicago - Dining room
Villa D' Citta
9.4 Wonderful
Lincoln Park₪1,520+
₪1,520+
Free Wi-Fi
Air Conditioning
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
8.8 Very good
South Side₪1,113+
₪1,113+
Parking
Air Conditioning
The Greenleaf House - Chicago - Kitchen
The Greenleaf House - Chicago - Kitchen
The Greenleaf House
8.1 Very good
Rogers Park₪237+
₪237+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
₪1,748+
₪1,748+
Air Conditioning
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
9.4 Wonderful
Near West Side₪1,037+
₪1,037+
Free Wi-Fi
Air Conditioning
The Sono Chicago - Chicago - Bedroom
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
9.5 Wonderful
Near North Side₪1,055+
₪1,055+
Parking
Free Wi-Fi
Air Conditioning
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
9.3 Wonderful
₪1,054+
₪1,054+
Parking
Free Wi-Fi
Air Conditioning
Rustic cottage-style condo within walking distance to downtown Homewood - Homewood - Kitchen
Rustic cottage-style condo within walking distance to downtown Homewood - Homewood - Kitchen
Rustic cottage-style condo within walking distance to downtown Homewood
Downtown₪814+
₪814+
Air Conditioning
Wicker Park Chicago - Chicago
Wicker Park Chicago - Chicago
Wicker Park Chicago
6.1 Okay
₪510+
₪510+
Pet friendly
Air Conditioning
Diversey Guest House - Chicago
Diversey Guest House - Chicago
Diversey Guest House
Lake View₪391+
₪391+
Free Wi-Fi
Four bedroom apartment - Chicago
Four bedroom apartment - Chicago
Four bedroom apartment
Lake View₪2,458+
₪2,458+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
A nice bedroom 10 min to downtown Chicago pet friendly - Chicago
A nice bedroom 10 min to downtown Chicago pet friendly - Chicago
A nice bedroom 10 min to downtown Chicago pet friendly
West Garfield Park₪131+
₪131+
Pet friendly
Large Room with King bed in the Lakeview - 3A - Chicago
Large Room with King bed in the Lakeview - 3A - Chicago
Large Room with King bed in the Lakeview - 3A
5.5 Fair
Lake View₪591+
₪591+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
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₪131 - ₪537₪537 - ₪942₪942 - ₪1,347₪1,347 - ₪1,748₪1,748+ per night

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KAYAK’s insights for bed & breakfasts in Chicago

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chicago with confidence.

Which month has the cheapest bed & breakfast rates in Chicago?

Bed & Breakfasts are cheapest in Chicago in February, with average rates of ₪1,039. In comparison, September is the most expensive month, with prices at ₪6,620.

What is the cheapest day of the week to book a bed & breakfast in Chicago?

Thursday offers the lowest rates in Chicago, with an average nightly price of ₪1,862. The highest prices are found on Saturday, with average rates at ₪3,973.
Find deals

How much is a Chicago bed & breakfast?

Here are our most popular & best value bed & breakfasts

2 stars and below

3 stars

Good to know

Low season

February

High season

September

Average price (weeknight)

₪606

Average price (weekend night)

₪887
Cheapest month to stay with an average 54% drop in price.
Most expensive month to stay with an average 192% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding Chicago bed & breakfast deals

  • If you want to ensure you grab a bargain, try to book more than 90 days before your stay to get the best price for a Chicago bed & breakfast.

FAQs when booking a bed & breakfast in Chicago

  • Is it cheaper to stay in a bed & breakfast than in a hotel in Chicago?

    The average price for a night in a bed & breakfast in Chicago is ₪375 compared to ₪363 for a night in a hotel.

Where to find the best bed & breakfasts in Chicago?

Our map will help you find the perfect bed & breakfast in Chicago by showing you the exact location of each bed & breakfast.

What Chicago bed & breakfast guests are talking about

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Hotels about topic

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Villa D' Citta - Chicago - Dining room
Villa D' Citta
9.4 Wonderful
Lincoln Park₪1,520+
₪1,520+
Free Wi-Fi
Air Conditioning
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Ray's Bucktown Bed And Breakfast
9.6 Wonderful
₪1,057+
₪1,057+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
8.8 Very good
South Side₪1,113+
₪1,113+
Parking
Air Conditioning

Popular topics

Everything you need to know for your stay in Chicago

Chicago bed & breakfast deals. Search for bed & breakfasts in Chicago. Find cheap bed & breakfasts in Chicago. KAYAK searches hundreds of travel sites to help you find cheap bed & breakfasts and book the room that suits you best.

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