Title: 20 Best B&B in Winnetka, IL - Bed and Breakfast from $72 | Expedia.com [Winnetka Travel Guide](https://expedia.com/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.com/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Vacation Rentals in Winnetka](https://expedia.com/Winnetka-Vacation-Rentals.d175751.Travel-Guide-VacationRentals)[Flights to Winnetka](https://expedia.com/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Car Rentals in Winnetka](https://expedia.com/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.com/Winnetka.d175751.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winnetka bed & breakfast ![Staircase](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/5b0f48e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/fbec7123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/a2ea72ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/fb4aa20c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Publishing House B&B [](https://www.expedia.com/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (196 reviews) "Very clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVEN $193 nightly $218 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/662a1d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Balcony](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/21ce57c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/4c515ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/8d057531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sono Chicago [](https://www.expedia.com/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) Near North Side 10/10 Exceptional (492 reviews) "Fantastic place! Very clean, kind and welcoming staff, great breakfast, and great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catie $122 nightly $143 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/cc909706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/1be0a5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/699f54e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/5a018673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dorothy's [](https://www.expedia.com/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) Lakeview 8.4/10 Very Good (106 reviews) "cozy and close to cool places" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter Fox $67 nightly $72 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) ![Double Room, Private Bathroom (Venetian) | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/8cf3a2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/7dbf8d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/a7524278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/bfcbb141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villa Toscana [](https://www.expedia.com/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) Lakeview 7.8/10 Good (630 reviews) "Good location. Nice room. Shared bath. Excellent value. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel $83 nightly $90 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) ![Spa](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/6c176329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/6c529c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/d3d95fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/8eb960ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ray's Bucktown B&B [](https://www.expedia.com/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information) Bucktown 9.8/10 Exceptional (390 reviews) "We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin $163 nightly $184 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/28d738d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/7986cc5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![51-inch flat-screen TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/a6a881dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom (1st Floor) | Living area | 51-inch flat-screen TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/f5474d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House 5863 - Chicago Bed and Breakfast [](https://www.expedia.com/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) Edgewater 9.2/10 Wonderful (498 reviews) "Wonderful room, very good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $158 nightly $186 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/2fdab583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/bfebe08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/dd4d353d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Florencia Suite | Egyptian cotton sheets, premium bedding, memory foam beds, in-room safe](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/fffe1dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa D' Citta [](https://www.expedia.com/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) Lincoln Park 9.4/10 Exceptional (114 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey $206 nightly $242 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/fd77852c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/e9f699a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Balcony, City View (Paulina)(Facing Train – Not for Light Sleepers) | Balcony](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/2b0abb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/4d62e2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wicker Park Inn [](https://www.expedia.com/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (260 reviews) "Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey $206 nightly $242 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/b288c54a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet Suite | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/bee2290f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oak Park Suite | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/05ff5c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden Suite | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/79fbc793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvey House Bed & Breakfast [](https://www.expedia.com/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) Oak Park 9.8/10 Exceptional (122 reviews) "Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth $231 nightly $256 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-05&endDate=2026-03-06®ionId=175751&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_175751) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Bed-And-Breakfast.d175751-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Bed-And-Breakfast.d175751-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winnetka Hotel Reviews ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Everything was clean and neat. " [](https://expedia.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Beautiful place" [](https://expedia.com/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Clean room, friendly staff " [](https://expedia.com/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Very good " [](https://expedia.com/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Classic older and well maintained hotel. " [](https://expedia.com/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg) ### LondonHouse Chicago, Curio Collection by Hilton 10/10 Excellent "Friendly staff " [](https://expedia.com/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "Staff was pleasant, breakfast was good and was sooo covenient to not have to worry about. My room was very tidy, the location was great, i walked to all of the places i wanted to go, in under 15mins. I am looking forwards to seeing chicago in the summer months and i would stay here again. " [](https://expedia.com/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg) ### Aloft Chicago Mag Mile 10/10 Excellent "Wonderful and friendly staff" [](https://expedia.com/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "The room was very nice and spacious! I traveled with my family, so it was 4 of us in which it was perfect, nice views as well! Great front desk." [](https://expedia.com/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ## Find out more about Winnetka ## Winnetka B&B information | Number of reviews | 2,588 | | ----------------- | ------ | | Accommodation | 12 B&B | | Lowest Price | $72 | | Highest Price | $256 | ## Frequently asked questions ### What is the nightly rate for a B&B in Winnetka? ### When is the best time to book a B&B in Winnetka? > July stands out as the most popular month to visit Winnetka, as residents and visitors alike take advantage of the sun-soaked days and festive community events. During this time, you can indulge in delightful strolls along the beach, savor local cuisine at outdoor eateries, and partake in various cultural activities that reflect the area's lively spirit. > > > If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, allowing for peaceful walks along the beach and the chance to enjoy the stunning fall foliage in the surrounding parks. It's also a lovely time for exploring local shops and cafes without the summer crowds. ### What is the difference between a Winnetka Bed and Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Home Alone House ](https://www.expedia.com/Home-Alone-House-Hotels.0-l553248635997949865-0.Travel-Guide-Filter-Hotels) - [Hotels near Winnetka Station ](https://www.expedia.com/Winnetka-Station-Hotels.d6214780.Travel-Guide-Hotels) - [Hotels near Chocolate Box ](https://www.expedia.com/Chocolate-Box-Hotels.0-l553248621532658670-0.Travel-Guide-Filter-Hotels) - [Vacation Homes in Winnetka Indian Hill Station ](https://www.expedia.com/Winnetka-Indian-Hill-Station-Private-Vacation-Homes.d6214771-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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