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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

These are the best prices for Oct 10 - 11.
Ray`s Bucktown B & B - Chicago
Ray`s Bucktown B & B
Chicago, IL
9.5Wonderful(286)
Parking
Free Wi-Fi
Pet friendly
$306+
Check availability
Villa D` Citta - Chicago - Living room
Villa D` Citta
Lincoln Park
9.3Wonderful(151)
Free Wi-Fi
$360+
Check availability
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
Near West Side
9.2Wonderful(113)
Free Wi-Fi
$273+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
Bridgeport
9.4Wonderful(119)
Parking
$356+
Check availability
House 5863- Bed and Breakfast - Adults Only - Chicago
House 5863- Bed and Breakfast - Adults Only
Edgewater
8.6Very good(38)
Free Wi-Fi
$212+
Check availability
Villa Toscana Guest House B&B - Chicago
Villa Toscana Guest House B&B
Lake View
7.8Good(156)
Parking
Free Wi-Fi
Pet friendly
$148+
Check availability
The Greenleaf House - Chicago
The Greenleaf House
Rogers Park
8.1Very good(285)
Parking
Free Wi-Fi
Pet friendly
$693+
Check availability
Oak Park/Harvey House Bed & Breakfast - Oak Park
Oak Park/Harvey House Bed & Breakfast
Oak Park, IL
9.2Wonderful(115)
Parking
Free Wi-Fi
$325+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL
10Wonderful(12)
Free Wi-Fi
$449+
Check availability
Just Minutes from Downtown Chicago - Chicago
Just Minutes from Downtown Chicago
Grand Boulevard
7.4Good(8)
Parking
Free Wi-Fi
$332+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
$107+
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 $115/night. In comparison, May is the most expensive month, with prices at $314/night.

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

Monday offers the lowest rates in Chicago, with an average nightly price of $211/night. The highest prices are found on Friday, with average rates at $489/night.

Which neighbourhood do KAYAK users most love to book their bed & breakfast in Chicago?

The most popular neighbourhood in Chicago among KAYAK users to search for a bed & breakfast is Lincoln Park, with an average price of $391. Hotel Lincoln, The Neighborhood Hotel - Lincoln Park Lp, and Villa D` Citta rank among the highest-rated hotels in Lincoln Park.

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

Book at least 50 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)

December
July
$267
$446
Cheapest month to stay with an average 73% drop in price.
Most expensive month to stay with an average 72% 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 December and March.
  • Bed & Breakfast room prices vary depending on many factors but you’ll likely find the best bed & breakfast deals in Chicago if you stay on a Monday. The most expensive day for bed & breakfast bookings is Friday.
  • If you want to ensure you grab a bargain, try to book at least 50 days before your stay to get the best price for a Chicago bed & breakfast.
  • The cheapest 3-star bed & breakfast in Chicago found on KAYAK in the last 2 weeks was $59, while the most expensive was $83.
  • 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 $322 compared to $416 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.

More options for your stay in Chicago