Chicago bed & breakfasts

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Booking Insights
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Best Chicago bed & breakfasts

These are the best prices for 15-22 Jun.
House 5863- Chicago's Premier Bed and Breakfast - Chicago
House 5863- Chicago's Premier Bed and Breakfast
Edgewater
8.4Very Good(34)
Free Wi-Fi
Air conditioning
R4 006+
Check availability
Villa D' Citta - Chicago - Living room
Villa D' Citta
Lincoln Park
9.2Wonderful(159)
Free Wi-Fi
Air conditioning
R6 682+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.3Wonderful(112)
Parking
Air conditioning
R6 706+
Check availability
The Villa Toscana - Chicago
The Villa Toscana
Lake View
8.0Very Good(137)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R4 216+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.5Wonderful(281)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R5 057+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.6Good(23)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 416+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
10Wonderful(9)
Air conditioning
R8 485+
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The Greenleaf House - Chicago - Building
The Greenleaf House
Rogers Park
8.5Very Good(274)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R14 149+
Check availability
Harvey House Bed And Breakfast - Oak Park
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.5Wonderful(119)
Parking
Free Wi-Fi
Air conditioning
R5 146+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
R1 768+
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?

Based on bed & breakfast prices in Chicago found by KAYAK users over the last 12 months.

Bed & Breakfasts are cheapest in Chicago in January, with average rates of R2 909/night. In comparison, October is the most expensive month, with prices at R5 189/night.

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 R2 560/night. The highest prices are found on Friday, with average rates at R6 038/night.

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

Book at least 44 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)

January
October
R3 672
R5 468
Cheapest month to stay with an average 75% drop in price.
Most expensive month to stay with an average 49% 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 44 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 14 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 R5 561 compared to R7 597 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

Everything you need to know for your stay in Chicago

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