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.

Best Chicago bed & breakfasts

Most recommended Chicago bed & breakfasts

Show all
The Villa Toscana - Chicago - Living room
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
The Greenleaf House - Chicago - Kitchen
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Dorothy's - Chicago - Living room
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
The Sono Chicago - Chicago - Bedroom
Parking
Free Wi-Fi
Air Conditioning
Harvey House Bed And Breakfast - Oak Park - Living room
Parking
Free Wi-Fi
Air Conditioning
Old Chicago Inn - Chicago
Free Wi-Fi
Pet friendly
Air Conditioning
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet friendly
Air Conditioning
Large Room with King bed in the Lakeview - 3A - Chicago
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
Parking
Free Wi-Fi
Pet friendly
Air Conditioning

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 December, with average rates of ₪1,021. In comparison, July is the most expensive month, with prices at ₪12,735.

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 ₪969. The highest prices are found on Saturday, with average rates at ₪6,647.

How much is a Chicago bed & breakfast?

Here are our most popular & best value bed & breakfasts

2 stars and below

3 stars

Good to know

Low season

December

High season

July

Average price (weeknight)

₪416

Average price (weekend night)

₪1,059
Cheapest month to stay with an average 53% drop in price.
Most expensive month to stay with an average 484% 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 more than 90 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 ₪271 compared to ₪413 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

Show all

Hotels about topic

Show all
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Parking
Free Wi-Fi
Pet friendly
Air Conditioning

Popular topics

Everything you need to know for your stay in Chicago

Chicago bed & breakfast deals. Search for bed & breakfasts in Chicago. Find cheap bed & breakfasts in Chicago. KAYAK searches hundreds of travel sites to help you find cheap bed & breakfasts and book the room that suits you best.

Not what you’re looking for? Find thousands of other hotels, flights and car rentals with KAYAK.