Chicago bed & breakfasts

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

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

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

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Chicago bed & breakfasts

Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(158)
Free Wi-Fi
Air conditioning
AED 1,343+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Building
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(277)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 971+
Check availability
House 5863- Chicago's Premier Bed and Breakfast - Chicago - Bedroom
House 5863- Chicago's Premier Bed and Breakfast
Edgewater
9.0Wonderful(32)
Free Wi-Fi
Air conditioning
AED 930+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.5Wonderful(112)
Parking
Air conditioning
AED 1,193+
Check availability
The Villa Toscana - Chicago - Lounge
The Villa Toscana
Lake View
7.9Good(125)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 556+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
7.5Good(19)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 383+
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
AED 1,922+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.6Wonderful(119)
Parking
Free Wi-Fi
Air conditioning
AED 1,078+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
AED 393+
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 January, with average rates of AED 217/night. In comparison, May is the most expensive month, with prices at AED 1,152/night.

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 AED 241/night. The highest prices are found on Sunday, with average rates at AED 1,040/night.

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)

January
May
AED 613
AED 765
Cheapest month to stay with an average 71% drop in price.
Most expensive month to stay with an average 54% 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 AED 1,057 compared to AED 1,133 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

Complete your trip to Chicago

Flights to Chicago
Car rentals in Chicago