Chicago bed & breakfasts

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

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Millions of reviewsCheck ratings based on millions of real guest reviews.

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Recommended by KAYAK

Best Chicago bed & breakfasts

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2+ stars3+ stars4+ stars

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6+ Okay7+ Good8+ Great9+ Excellent

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R1 358 - R2 890R2 890 - R4 405R4 405 - R5 937R5 937 - R7 452R7 452+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended Chicago bed & breakfasts

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The Villa Toscana - Chicago - Living room
The Villa Toscana
Lake View
7.9Good(105)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 341+
Check availability
House 5863- Chicago's Premier Bed and Breakfast - Chicago - Bedroom
House 5863- Chicago's Premier Bed and Breakfast
Edgewater
9.0Wonderful(30)
Free Wi-Fi
Air conditioning
R3 388+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.3Wonderful(524)
Parking
Free Wi-Fi
Air conditioning
R4 874+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(160)
Free Wi-Fi
Air conditioning
R6 177+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.3Wonderful(110)
Parking
Air conditioning
R5 311+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.6Good(13)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 095+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Dining room
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(273)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R4 773+
Check availability
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley! - Chicago - Dining room
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Chicago, IL, United States
9.6Wonderful(19)
Air conditioning
R7 126+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
10Wonderful(6)
Air conditioning
R9 081+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.5Wonderful(119)
Parking
Free Wi-Fi
Air conditioning
R5 209+
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
9.2Wonderful(8)
Air conditioning
R4 353+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very Good(1)
Free Wi-Fi
Air conditioning
R3 186+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
R1 863+
Check availability
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
9.0Wonderful(3)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 134+
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?

Thursday offers the lowest rates in Chicago, with an average nightly price of R2 874. The highest prices are found on Friday, with average rates at R7 181.

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

Book at least 49 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)

March
April
R3 653
R5 552
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 99% 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 49 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 R4 180 compared to R4 913 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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The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.3Wonderful(524)
Parking
Free Wi-Fi
Air conditioning
R4 874+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(160)
Free Wi-Fi
Air conditioning
R6 177+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.3Wonderful(110)
Parking
Air conditioning
R5 311+
Check availability

Everything you need to know for your stay in Chicago

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