Chicago bed & breakfasts

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

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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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R624 - R2 359R2 359 - R4 076R4 076 - R5 810R5 810 - R7 527R7 527+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended Chicago bed & breakfasts

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House 5863- Chicago's Premier Bed and Breakfast - Chicago - Bedroom
House 5863- Chicago's Premier Bed and Breakfast
Edgewater
8.7Very Good(30)
Free Wi-Fi
Air conditioning
R3 658+
Check availability
The Villa Toscana - Chicago - Living room
The Villa Toscana
Lake View
7.7Good(95)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 730+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(158)
Free Wi-Fi
Air conditioning
R6 317+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.3Wonderful(517)
Parking
Free Wi-Fi
Air conditioning
R6 085+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.2Wonderful(109)
Parking
Air conditioning
R5 290+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
10Wonderful(4)
Air conditioning
R9 437+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.7Good(11)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 217+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Dining room
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(269)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R4 718+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.6Wonderful(118)
Parking
Free Wi-Fi
Air conditioning
R5 363+
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
R3 868+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very Good(1)
Free Wi-Fi
Air conditioning
R3 174+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
R1 856+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet-friendly
Air conditioning
R2 424+
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
R624+
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 122+
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.

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

Bed & Breakfasts are cheapest in Chicago in March, with average rates of R25 023. In comparison, April is the most expensive month, with prices at R123 692.

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

Wednesday offers the lowest rates in Chicago, with an average nightly price of R35 528. The highest prices are found on Tuesday, with average rates at R73 850.

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.
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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 169
R3 572
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 97% 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 R280 compared to R384 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(517)
Parking
Free Wi-Fi
Air conditioning
R6 085+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(158)
Free Wi-Fi
Air conditioning
R6 317+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.2Wonderful(109)
Parking
Air conditioning
R5 290+
Check availability

Everything you need to know for your stay in Chicago

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