South Africa
ZAR

Chicago bed & breakfasts

KAYAK searches hundreds of travel sites at once for Bed & Breakfasts in Chicago

Here is why travellers 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

These are the best prices for 14-21 Oct.
Villa D` Citta - Chicago - Living room
Villa D` Citta
Lincoln Park
9.3Wonderful(151)
Free Wi-Fi
Air conditioning
R6 170+
Check availability
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
Bridgeport
9.4Wonderful(119)
Parking
Air conditioning
R5 899+
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
Air conditioning
R3 508+
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
Air conditioning
R2 517+
Check availability
Ray`s Bucktown B & B - Chicago
Ray`s Bucktown B & B
Chicago, IL, United States
9.5Wonderful(286)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R5 059+
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
Air conditioning
R4 544+
Check availability
Unique Chicago Penthouse Loft - Amazing Deal & Location - Chicago - Kitchen
Unique Chicago Penthouse Loft - Amazing Deal & Location
Chicago, IL, United States
10Wonderful(12)
Free Wi-Fi
Air conditioning
R7 435+
Check availability
The Greenleaf House - Chicago
The Greenleaf House
Rogers Park
8.7Very Good(285)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R11 324+
Check availability
Oak Park/Harvey House Bed & Breakfast - Oak Park
Oak Park/Harvey House Bed & Breakfast
Oak Park, IL, United States
9.2Wonderful(115)
Parking
Free Wi-Fi
Air conditioning
R5 393+
Check availability
Diversey Guest House - Chicago
Diversey Guest House
Lake View
Free Wi-Fi
R1 772+
Check availability
Just Minutes from Downtown Chicago - Chicago
Just Minutes from Downtown Chicago
Grand Boulevard
7.4Good(8)
Parking
Free Wi-Fi
Air conditioning
R5 510+
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 R1 905/night. In comparison, May is the most expensive month, with prices at R5 201/night.

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 R4 116/night. The highest prices are found on Friday, with average rates at R8 094/night.

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
R5 285
R7 423
Cheapest month to stay with an average 76% drop in price.
Most expensive month to stay with an average 75% 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 50 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 R5 333 compared to R6 894 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

Complete your trip to Chicago

Flights to Chicago
Car hire in Chicago