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

Most recommended Chicago bed & breakfasts

Show all
The Villa Toscana - Chicago - Living room
Parking
Free Wi-Fi
Pet-friendly
Ray's Bucktown Bed And Breakfast - Chicago - Bedroom
Parking
Free Wi-Fi
Pet-friendly
Dorothy's - Chicago - Living room
Parking
Free Wi-Fi
Pet-friendly
Wicker Park Chicago - Chicago
Wicker Park Chicago
Chicago, IL, United States
6.1Okay(48)
Pet-friendly
The Ashlin House - Whiting
The Ashlin House
Whiting, IN, United States
8.7Very Good(3)
Parking
Free Wi-Fi
Pet-friendly
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.

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

Sunday offers the lowest rates in Chicago, with an average nightly price of RM 3,861. The highest prices are found on Saturday, with average rates at RM 8,191.

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

Book at least 12 days before your stay begins to get the best price for your Chicago bed & breakfast.

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
August
RM 1,083
RM 1,690
Cheapest month to stay with an average 66% drop in price.
Most expensive month to stay with an average 61% 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

  • What are the best bed & breakfasts near Merchandising Mart?

    Merchandising Mart is a popular area in Chicago and there are many bed & breakfasts closeby. Check out The Publishing House Bed and Breakfast or The Sono Chicago for hostels recommended by KAYAK that are within walking distance of Merchandising Mart.

  • 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 RM 365 compared to RM 427 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

Everything you need to know for your stay in Chicago

Search cheap hotels with KAYAK. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. KAYAK searches hundreds of hotel booking sites to help you find hotels and book hotels that suit you best. Since KAYAK searches many hotel sites at once, you can find discount hotels quickly. Discover hotel discounts now and make your hotel reservation today.