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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(59)
Parking
Free Wi-Fi
Pet friendly
C$ 309+
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
C$ 424+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.4Wonderful(164)
Free Wi-Fi
C$ 554+
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
C$ 422+
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
C$ 434+
Check availability
The Greenleaf House - Chicago - Kitchen
The Greenleaf House
Rogers Park
8.1Very good(267)
Parking
Free Wi-Fi
Pet friendly
C$ 102+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
C$ 727+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.7Good(3)
Parking
Free Wi-Fi
Pet friendly
C$ 284+
Check availability
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
Near West Side
9.5Wonderful(108)
Free Wi-Fi
C$ 409+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.5Wonderful(481)
Parking
Free Wi-Fi
C$ 523+
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
C$ 309+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very good(1)
Free Wi-Fi
Pet friendly
C$ 253+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet friendly
C$ 194+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
C$ 148+
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
C$ 50+
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
C$ 224+
Check availability
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
Parking
Free Wi-Fi
Pet friendly
C$ 249+
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 C$ 150. In comparison, July is the most expensive month, with prices at C$ 1,867.

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 C$ 142. The highest prices are found on Saturday, with average rates at C$ 974.
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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)

C$ 159

Average price (weekend night)

C$ 406
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’re looking for a cheap bed & breakfast in Chicago, you should consider going during the low season. You’ll generally find lower-priced bed & breakfasts in Chicago in January and October.
  • Bed & Breakfast room prices vary depending on many factors but you’ll likely find the best bed & breakfast deals in Chicago if you stay on a Wednesday. The most expensive day for bed & breakfast bookings is Friday.
  • 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.
  • Don’t know how much time you need to see all the sights? KAYAK users usually book their bed & breakfast in Chicago for 2 days.
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FAQs when booking a bed & breakfast in Chicago

  • What are the best bed & breakfasts near Magnificent Mile?

    Magnificent Mile is a popular area in Chicago and there are many bed & breakfasts closeby. Check out The Publishing House Bed and Breakfast or The Sono Chicago for hostels recommended by KAYAK that are within walking distance of Magnificent Mile.

  • 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 C$ 273 compared to C$ 415 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
C$ 554+
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
C$ 424+
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
C$ 422+
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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