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Chicago bed & breakfasts

KAYAK searches 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
Lake View
7.5Good(60)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪841+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.5Wonderful(267)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪1,107+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.4Wonderful(164)
Free Wi-Fi
Air Conditioning
₪1,437+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
8.8Very good(107)
Parking
Air Conditioning
₪1,103+
Check availability
The Greenleaf House - Chicago - Kitchen
The Greenleaf House
Rogers Park
8.1Very good(267)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪279+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
Air Conditioning
₪1,896+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.7Good(3)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪829+
Check availability
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
Near West Side
9.5Wonderful(109)
Free Wi-Fi
Air Conditioning
₪1,090+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.5Wonderful(483)
Parking
Free Wi-Fi
Air Conditioning
₪1,352+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.4Wonderful(113)
Parking
Free Wi-Fi
Air Conditioning
₪1,137+
Check availability
Rustic cottage-style condo within walking distance to downtown Homewood - Homewood - Kitchen
Rustic cottage-style condo within walking distance to downtown Homewood
Downtown
Air Conditioning
₪807+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very good(1)
Free Wi-Fi
Pet friendly
Air Conditioning
₪662+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet friendly
Air Conditioning
₪505+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
₪387+
Check availability
A nice bedroom 10 min to downtown Chicago pet friendly - Chicago
A nice bedroom 10 min to downtown Chicago pet friendly
West Garfield Park
Pet friendly
₪130+
Check availability
Large Room with King bed in the Lakeview - 3A - Chicago
Large Room with King bed in the Lakeview - 3A
Lake View
5.5Fair(3)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪586+
Check availability
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪651+
Check availability
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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 December, with average rates of ₪1,021. In comparison, July is the most expensive month, with prices at ₪12,735.

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

Monday offers the lowest rates in Chicago, with an average nightly price of ₪969. The highest prices are found on Saturday, with average rates at ₪6,647.
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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

December

High season

July

Average price (weeknight)

₪416

Average price (weekend night)

₪1,059
Cheapest month to stay with an average 53% drop in price.
Most expensive month to stay with an average 484% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's 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 ₪271 compared to ₪413 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
Lincoln Park
9.4Wonderful(164)
Free Wi-Fi
Air Conditioning
₪1,437+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.5Wonderful(267)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪1,107+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
8.8Very good(107)
Parking
Air Conditioning
₪1,103+
Check availability

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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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