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Chicago bed & breakfasts

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Best Chicago bed & breakfasts

Most recommended Chicago bed & breakfasts

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Ray's Bucktown Bed And Breakfast - Chicago - Lobby
Ray's Bucktown Bed And Breakfast
9.6 Wonderful
S$ 366+
S$ 366+
Parking
Free Wi-Fi
Pet-friendly
Villa D' Citta - Chicago - Dining room
Villa D' Citta
9 Wonderful
Lincoln ParkS$ 567+
S$ 567+
Free Wi-Fi
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
9.4 Wonderful
South SideS$ 412+
S$ 412+
Parking
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast - Chicago - Living room
The Publishing House Bed and Breakfast
9.6 Wonderful
DowntownS$ 427+
S$ 427+
Free Wi-Fi
The Sono Chicago - Chicago - Bedroom
The Sono Chicago - Chicago - Bedroom
The Sono Chicago
9.5 Wonderful
Near North SideS$ 487+
S$ 487+
Parking
Free Wi-Fi
Harvey House Bed And Breakfast - Oak Park - Bedroom
Harvey House Bed And Breakfast - Oak Park - Bedroom
Harvey House Bed And Breakfast
9.3 Wonderful
S$ 433+
S$ 433+
Parking
Free Wi-Fi
Rustic cottage-style condo within walking distance to downtown Homewood - Homewood - Kitchen
Rustic cottage-style condo within walking distance to downtown Homewood - Homewood - Kitchen
Rustic cottage-style condo within walking distance to downtown Homewood
S$ 316+
S$ 316+
Wicker Park Chicago - Chicago
Wicker Park Chicago - Chicago
Wicker Park Chicago
S$ 189+
S$ 189+
Pet-friendly
The Greenleaf House - Chicago
The Greenleaf House - Chicago
The Greenleaf House
8.3 Very Good
Rogers ParkS$ 968+
S$ 968+
Parking
Free Wi-Fi
Pet-friendly
Diversey Guest House - Chicago
Diversey Guest House - Chicago
Diversey Guest House
Lake ViewS$ 144+
S$ 144+
Free Wi-Fi
A nice bedroom 10 min to downtown Chicago pet friendly - Chicago
A nice bedroom 10 min to downtown Chicago pet friendly - Chicago
A nice bedroom 10 min to downtown Chicago pet friendly
West Garfield ParkS$ 49+
S$ 49+
Pet-friendly
House Of Two Urns B&B - Chicago
House Of Two Urns B&B - Chicago
House Of Two Urns B&B
West TownS$ 1,402+
S$ 1,402+
Just Minutes from Downtown Chicago - Chicago
Just Minutes from Downtown Chicago - Chicago
Just Minutes from Downtown Chicago
9.3 Wonderful
South SideS$ 336+
S$ 336+
Parking
Free Wi-Fi
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S$ 49 - S$ 388S$ 388 - S$ 725S$ 725 - S$ 1,064S$ 1,064 - S$ 1,402S$ 1,402+ per night

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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

January

High season

September

Average price (weeknight)

S$ 288

Average price (weekend night)

S$ 240
Cheapest month to stay with an average 29% drop in price.
Most expensive month to stay with an average 490% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a bed & breakfast in Chicago

Price per night / 3-star bed & breakfast. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

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 February.
  • 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 Thursday. The most expensive day for bed & breakfast bookings is Saturday.
  • 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

  • What are the best bed & breakfasts near Oak Street Beach?

    Oak Street Beach is a popular area in Chicago and there are many bed & breakfasts closeby. Check out Villa D' Citta or The Sono Chicago for hostels recommended by KAYAK that are within walking distance of Oak Street Beach.

  • How much does a bed & breakfast cost in Chicago?

    Bed & Breakfast prices in Chicago can vary depending on a number of factors. The average price for a bed & breakfast in Chicago is S$ 372 but KAYAK users have found bed & breakfasts for as cheap as S$ 85 in the last 3 days.

  • 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 S$ 372 compared to S$ 431 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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What Chicago bed & breakfast guests are talking about

Hotels about topic

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Villa D' Citta - Chicago - Dining room
Villa D' Citta
9 Wonderful
Lincoln ParkS$ 567+
S$ 567+
Free Wi-Fi
Ray's Bucktown Bed And Breakfast - Chicago - Lobby
Ray's Bucktown Bed And Breakfast
9.6 Wonderful
S$ 366+
S$ 366+
Parking
Free Wi-Fi
Pet-friendly
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A. - Chicago - Bedroom
The Polo Inn Bridgeport U.S.A.
9.4 Wonderful
South SideS$ 412+
S$ 412+
Parking

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