Chicago bed & breakfasts

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

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Booking Insights
Recommended by KAYAK

Best Chicago bed & breakfasts

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135 ﷼ - 517 ﷼517 ﷼ - 899 ﷼899 ﷼ - 1,282 ﷼1,282 ﷼ - 1,660 ﷼1,660 ﷼+ per night

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Most recommended Chicago bed & breakfasts

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The Villa Toscana - Chicago - Living room
The Villa Toscana
Lake View
7.5Good(82)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
844 ﷼+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(268)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
1,157 ﷼+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.5Wonderful(163)
Free Wi-Fi
Air Conditioning
1,534 ﷼+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
8.9Very good(110)
Parking
Air Conditioning
1,143 ﷼+
Check availability
The Greenleaf House - Chicago - Kitchen
The Greenleaf House
Rogers Park
8.2Very good(269)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
334 ﷼+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
Air Conditioning
2,023 ﷼+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.9Good(4)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
814 ﷼+
Check availability
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
Near West Side
9.6Wonderful(109)
Free Wi-Fi
Air Conditioning
1,131 ﷼+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.5Wonderful(501)
Parking
Free Wi-Fi
Air Conditioning
1,455 ﷼+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.5Wonderful(114)
Parking
Free Wi-Fi
Air Conditioning
1,241 ﷼+
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
836 ﷼+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very good(1)
Free Wi-Fi
Pet friendly
Air Conditioning
686 ﷼+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet friendly
Air Conditioning
524 ﷼+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
401 ﷼+
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
135 ﷼+
Check availability
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
8.7Very good(3)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
637 ﷼+
Check availability
Booking Insights

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.

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

Friday offers the lowest rates in Chicago, with an average nightly price of 2,556 ﷼. The highest prices are found on Wednesday, with average rates at 4,720 ﷼.

How early should you book a bed & breakfast in Chicago?

Book at least 8 days before your stay begins to get the best price for your Chicago bed & breakfast.
Find deals

How much is a Chicago bed & breakfast?

Here are our most popular & best value bed & breakfasts

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
May
921 ﷼
800 ﷼
Cheapest month to stay with an average 64% drop in price.
Most expensive month to stay with an average 59% 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 at least 8 days before your stay to get the best price for a Chicago bed & breakfast.

FAQs when booking a bed & breakfast in Chicago

  • What are the best bed & breakfasts near Michigan Avenue?

    Michigan Avenue 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 Michigan Avenue.

  • 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 366 ﷼ compared to 427 ﷼ 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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Popular topics

Hotels about topic

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Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.5Wonderful(163)
Free Wi-Fi
Air Conditioning
1,534 ﷼+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(268)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
1,157 ﷼+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
8.9Very good(110)
Parking
Air Conditioning
1,143 ﷼+
Check availability

Everything you need to know for your stay in Chicago

Search cheap hotels with KAYAK. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. KAYAK searches hundreds of hotel booking sites to help you find hotels and book hotels that suit you best. Since KAYAK searches many hotel sites at once, you can find discount hotels quickly. Discover hotel discounts now and make your hotel reservation today.