Chicago bed & breakfasts

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Booking Insights
Recommended by KAYAK

Best Chicago bed & breakfasts

These are the best prices for Aug 16 - 23.
Ray's Bucktown Bed And Breakfast - Chicago
Ray's Bucktown Bed And Breakfast
Chicago, IL
9.5Wonderful(284)
Parking
Free Wi-Fi
Pet friendly
$294+
Check availability
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
Near West Side
9.3Wonderful(111)
Free Wi-Fi
$352+
Check availability
Villa D' Citta - Chicago - Living room
Villa D' Citta
Lincoln Park
9.2Wonderful(156)
Free Wi-Fi
$395+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
Bridgeport
9.3Wonderful(115)
Parking
$406+
Check availability
Dorothy`s - Chicago - Living room
Dorothy`s
Lake View
7.6Good(28)
Parking
Free Wi-Fi
Pet friendly
$179+
Check availability
The Greenleaf House - Chicago
The Greenleaf House
Rogers Park
9.0Wonderful(278)
Parking
Free Wi-Fi
Pet friendly
$91+
Check availability
House 5863- Chicago's Premier Bed and Breakfast - Chicago
House 5863- Chicago's Premier Bed and Breakfast
Edgewater
8.5Very good(36)
Free Wi-Fi
$238+
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The Villa Toscana - Chicago
The Villa Toscana
Lake View
7.9Good(146)
Parking
Free Wi-Fi
Pet friendly
$240+
Check availability
Oak Park/Harvey House Bed & Breakfast - Oak Park
Oak Park/Harvey House Bed & Breakfast
Oak Park, IL
9.2Wonderful(120)
Parking
Free Wi-Fi
$334+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL
10Wonderful(9)
$470+
Check availability
Just Minutes from Downtown Chicago - Chicago
Just Minutes from Downtown Chicago
Grand Boulevard
8.0Very good(6)
Parking
Free Wi-Fi
$352+
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?

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 $99/night. In comparison, May is the most expensive month, with prices at $281/night.

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

Tuesday offers the lowest rates in Chicago, with an average nightly price of $149/night. The highest prices are found on Friday, with average rates at $366/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 $371. Hotel Lincoln, Chicago Getaway Hostel, and The Neighborhood Hotel - Lincoln Park Lp rank among the highest-rated hotels in Lincoln Park.

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

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

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)

January
August
$218
$366
Cheapest month to stay with an average 77% drop in price.
Most expensive month to stay with an average 31% 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 January 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 Tuesday. 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 $109, while the most expensive was $408.
  • 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 $414 compared to $487 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