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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2+ stars3+ stars4+ stars

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6+ Okay7+ Good8+ Great9+ Excellent

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R645 - R2 471R2 471 - R4 297R4 297 - R6 123R6 123 - R7 931R7 931+ per night

Search by freebies

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
7.5Good(82)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R4 033+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.5Wonderful(163)
Free Wi-Fi
Air conditioning
R7 331+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.5Wonderful(501)
Parking
Free Wi-Fi
Air conditioning
R6 951+
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
R5 461+
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
R5 530+
Check availability
The Greenleaf House - Chicago - Kitchen
The Greenleaf House
Rogers Park
8.2Very Good(269)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R1 593+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
Air conditioning
R9 663+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.9Good(4)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 877+
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
R5 405+
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
R5 932+
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
R3 993+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very Good(1)
Free Wi-Fi
Pet-friendly
Air conditioning
R3 276+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet-friendly
Air conditioning
R2 502+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
R1 916+
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
R645+
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
R3 044+
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 R58 350. The highest prices are found on Wednesday, with average rates at R107 754.

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
R4 401
R3 824
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’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 February and December.
  • 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.
  • 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.

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 R366 compared to R427 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
9.5Wonderful(501)
Parking
Free Wi-Fi
Air conditioning
R6 951+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.5Wonderful(163)
Free Wi-Fi
Air conditioning
R7 331+
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
R5 461+
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.