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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£27 - £100£100 - £174£174 - £248£248 - £322£322+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended Chicago bed & breakfasts

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House 5863- Chicago's Premier Bed and Breakfast - Chicago - Bedroom
House 5863- Chicago's Premier Bed and Breakfast
Edgewater
8.7Very Good(30)
Free Wi-Fi
Air conditioning
£160+
Check availability
The Villa Toscana - Chicago - Living room
The Villa Toscana
Lake View
7.7Good(94)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£113+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Dining room
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(268)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£210+
Check availability
Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(158)
Free Wi-Fi
Air conditioning
£278+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.2Wonderful(109)
Parking
Air conditioning
£225+
Check availability
Harvey House Bed And Breakfast - Oak Park - Living room
Harvey House Bed And Breakfast
Oak Park, IL, United States
9.6Wonderful(117)
Parking
Free Wi-Fi
Air conditioning
£230+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
10Wonderful(4)
Air conditioning
£402+
Check availability
Dorothy's - Chicago - Living room
Dorothy's
Lake View
6.4Okay(5)
Air conditioning
£92+
Check availability
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
Near North Side
9.3Wonderful(516)
Parking
Free Wi-Fi
Air conditioning
£264+
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
9.2Wonderful(8)
Air conditioning
£165+
Check availability
Old Chicago Inn - Chicago
Old Chicago Inn
Lake View
8.0Very Good(1)
Free Wi-Fi
Air conditioning
£135+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
£79+
Check availability
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet-friendly
Air conditioning
£103+
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
£27+
Check availability
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
9.0Wonderful(3)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£133+
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 £44. In comparison, May is the most expensive month, with prices at £196.

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 £64. The highest prices are found on Saturday, with average rates at £244.

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.
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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
£136
£265
Cheapest month to stay with an average 59% drop in price.
Most expensive month to stay with an average 84% 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 August and April.
  • 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 Wednesday.
  • 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 £286 compared to £406 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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Villa D' Citta - Chicago - Dining room
Villa D' Citta
Lincoln Park
9.6Wonderful(158)
Free Wi-Fi
Air conditioning
£278+
Check availability
Ray's Bucktown Bed And Breakfast - Chicago - Dining room
Ray's Bucktown Bed And Breakfast
Chicago, IL, United States
9.4Wonderful(268)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£210+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
South Side
9.2Wonderful(109)
Parking
Air conditioning
£225+
Check availability

Everything you need to know for your stay in Chicago