Title: 20 Best B&B in Winnetka, IL - Bed and Breakfast from $70 | 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 [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [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) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-05-15&endDate=2026-05-17&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 (198 reviews) "Very clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVEN $193 nightly $218 total Mar 31 - Apr 1 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) ![Interior entrance](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/84ce68c2.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) ![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) ### The Sono Chicago [](https://www.expedia.com/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) Near North Side 10/10 Exceptional (497 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 $119 nightly $140 total Mar 24 - Mar 25 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) ![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) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/699f54e3.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) ### Dorothy's [](https://www.expedia.com/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) Lakeview 8.4/10 Very Good (109 reviews) "cozy and close to cool places" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter Fox $65 nightly $70 total Mar 24 - Mar 25 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) ![Lounge](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/bfcbb141.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) ### The Villa Toscana [](https://www.expedia.com/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) Lakeview 7.8/10 Good (632 reviews) "Overall the stay was fantastic looking forward to booking here again in the future " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rico $90 nightly $98 total Mar 18 - Mar 19 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) ![Front of property](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/67423b1d.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 (394 reviews) "Best everrrrr" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew $163 nightly $184 total Mar 18 - Mar 19 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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/e7b04404.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) ### 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 (499 reviews) "Wonderful room, very good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $195 nightly $229 total Mar 30 - Mar 31 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) ![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) ![Reception](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/dd4d353d.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) ### Villa D' Citta [](https://www.expedia.com/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) Lincoln Park 9.4/10 Exceptional (115 reviews) "Clean property, friendly staff, unique experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon $206 nightly $242 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Villa-D-Citta.h22299604.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) ![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) ![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) ![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 (123 reviews) "The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy $231 nightly $256 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.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) ![Room, 1 King Bed (Wolcott) | Premium bedding, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/8c2ae649.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) ### Wicker Park Inn [](https://www.expedia.com/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (261 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 $220 nightly $259 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Wicker-Park-Inn.h529114.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=2026-03-31&endDate=2026-04-01®ionId=175751&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg) ### Fairmont Chicago at Millennium Park 10/10 Excellent "😉✌️🇺🇲All in all, I really enjoyed everything. Thank you for the warm welcome. I hope the weather will be better next time." [](https://expedia.com/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 8/10 Good "Beds didn't feel like queens. Wish they'd give four pillow per bed rather than three." [](https://expedia.com/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 8/10 Good "The view was amazing! The restaurant downstairs was great! It was very hot in our room even with the windows open and the pullout couch was extremely uncomfortable. " [](https://expedia.com/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![L7 Chicago by LOTTE](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bb12c333_y.jpg) ### L7 Chicago by LOTTE 8/10 Good "Booked deluxe river view, but it was really a partial view from the side" [](https://expedia.com/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Good" [](https://expedia.com/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg) ### Congress Plaza Hotel 4/10 Poor "The place is clean. But it’s definitely a different vibe than the pictures. Staff wasn’t rude but didn’t go out of their way to help me or anything. Stayed on my own and had to park car and bring luggage around by myself. And then had the security guard joke that the buckingham wing my room was in is the haunted section…. I know the hotel has a reputation of being haunted but to tell a girl that’s obviously by herself? I was too freaked out to sleep the entire first night I stayed." [](https://expedia.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 8/10 Good "The shower pressure is awful and doesn’t get hot " [](https://expedia.com/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "The hotel is centrally located in Downtown Chicago with several eateries close by and walking distance from major attractions. We will definitely stay here again." [](https://expedia.com/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![The Chicago Hotel Collection Ambassador Gold Coast](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475_y.jpg) ### The Chicago Hotel Collection Ambassador Gold Coast 8/10 Good "I love the location.. not too close to the city but close enough.. great restaurants close by.. and all I will stay there again" [](https://expedia.com/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) ## Find out more about Winnetka ## Winnetka B&B information | Number of reviews | 1,935 | | ----------------- | ------ | | Accommodation | 12 B&B | | Lowest Price | $70 | | 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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