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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R637 - R2 444R2 444 - R4 232R4 232 - R6 038R6 038 - R7 827R7 827+ 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
7.5Good(83)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 647+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(163)
Free Wi-Fi
Air conditioning
R7 366+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.5Wonderful(505)
Parking
Free Wi-Fi
Air conditioning
R7 005+
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 401+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Dining room
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.3Wonderful(267)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R5 418+
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 700+
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 634+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
8.1Very Good(4)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 862+
Check availability
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
Near West Side
9.4Wonderful(110)
Free Wi-Fi
Air conditioning
R4 814+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.5Wonderful(116)
Parking
Free Wi-Fi
Air conditioning
R5 859+
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 949+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very Good(1)
Free Wi-Fi
Pet-friendly
Air conditioning
R3 240+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet-friendly
Air conditioning
R2 475+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
R1 895+
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
R637+
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 187+
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 April, with average rates of R25 059. In comparison, May is the most expensive month, with prices at R111 348.

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 R65 366. The highest prices are found on Friday, with average rates at R117 785.

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

Book at least 12 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)

April
May
R4 675
R6 453
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 49 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 R371 compared to R412 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(505)
Parking
Free Wi-Fi
Air conditioning
R7 005+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(163)
Free Wi-Fi
Air conditioning
R7 366+
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 401+
Check availability

Everything you need to know for your stay in Chicago

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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.