Title: 20 Best B&B in Winnetka, IL - Bed and Breakfast from $95 | 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 [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 weeks [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-06-05&endDate=2026-06-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winnetka bed & breakfast ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/662a1d77.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) ![Interior entrance](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/84ce68c2.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 (501 reviews) "Really happy with my choice of this lodging. Centrally located on a quiet street. Very new decor and bedding. Breakfast was good and adequate." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy $119 nightly $140 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) ![Staircase](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/5b0f48e0.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) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/a2ea72ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/86e1fd36.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 (199 reviews) "Very clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVEN $184 nightly $208 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.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 daily continental breakfast](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/82b0e4a1.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 (111 reviews) "cozy and close to cool places" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter Fox $86 nightly $95 total Apr 14 - Apr 15 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/7dbf8d2f.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 (633 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 $109 nightly $121 total Apr 15 - Apr 16 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) ![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) ![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 (396 reviews) "The breakfast alone was worth the trip! Warm, generous, eclectic, this place goes out of their way to welcome their guests. And they’re PET FRIENDLY. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter $168 nightly $190 total Apr 12 - Apr 13 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) ![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) ![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) ### 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 $184 nightly $216 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/fe13bf55.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) ![Courtyard](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/2fdab583.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 (116 reviews) "Everything was perfect. The food was really yummy I would love the salsa recipe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Earl $206 nightly $242 total Apr 13 - Apr 14 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) ![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) ![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) ### Harvey House Bed & Breakfast [](https://www.expedia.com/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) Oak Park 9.8/10 Exceptional (124 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 Apr 22 - Apr 23 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/b5e94ee1.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) ![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) ### Wicker Park Inn [](https://www.expedia.com/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (261 reviews) "Everything was good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $220 nightly $259 total Apr 26 - Apr 27 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=2026-04-23&endDate=2026-04-24®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 ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b_y.jpg) ### Swissotel - Chicago 10/10 Excellent "Nice rooms, great view" [](https://expedia.com/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a_y.jpg) ### Aloft Chicago Mag Mile 10/10 Excellent "Was fairly nice I'd say the only thing or things I didn't like was the extra $45 parking but if you download the app spot hero you'll be able to find cheaper parking around you and for breakfast you had to pay an extra $31 but otherwise in that the room was excellent although at first the staff said I didn't pay for a City View room but I showed them my Expedia purchase and they gave me the City View room the pool and gym were awesome The View was awesome they should add a hot tub to the pool section otherwise than that I enjoyed!" [](https://expedia.com/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/w5771h3835x0y5-963f61be_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Great stay, clean room only few minor things staff was friendly and helpful, wish the coffee and food stand was open longer than it was. Wild have liked and evening snack instead of a full meal" [](https://expedia.com/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "in a great location, with beautiful rooms and views! shower situation is weird as the wall is blurred but shown to the whole room. if your bed is next to the shower side of the bathroom be prepared to be woken up with how bright it will be as the wall is blurred not a legit wall." [](https://expedia.com/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.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 "I have travelled for most of my business career. As a result, I have had the opportunity to stay in numerous hotels across the US and internationally. Here are the pluses for The Riu Plaza Chicago: 1) Brand new. Spotlessly clean-very comfortable beds and new linens. Pillows soft and firm, just right balance. 2) Bathroom had a DOOR into it. Thank you for the privacy. 3) Shower was great. I enjoyed the enormous shower head. 4) Coffee maker was simple and easy to use. I liked the creamers instead of the powder variety. 5) Ample lighting throughout the entire room. 6) Your breakfast was top-notch. Great variety for everyone including foreign visitors. The dining room was very spacious. Negatives 1) I personally prefer carpeted hallways and rooms. It cuts down on noise. Something to think about going forward. 2) There is no shelving near or around the sick. One sick was sufficient. It consumed the space to lay shaving kits or whatever. Something to rethink. Perhaps something could be installed still. 3) The remote on the TV was really almost impossible to use. I gave up trying. Sometimes, simplicity helps. I had to return a widescreen TV for this very reason. Per the salesman who sold it to me understood exactly what I experienced at home. 4) Trays would have been helpful. I had to make several trips just to get my breakfast set. You can't carry coffee cups and a plate at the same time. This is just one example. That could be remedied easily." [](https://expedia.com/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.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 "The rooms were great and we enjoyed the view of Chicago. The mezzanine and hallways were noisy on Easter night (and especially on the night before Easter) but the kids were sleeping on the fold-out couch and they didn’t mind, but the bedroom was quiet because it faced the outside. We loved the breakfast and happy hour (2 free alcohol drinks for adults and nachos, pretzels, pasta salad, and fountain drinks for everyone - super fun!!) It was a great trip to Chicago - and we loved how close the red line was - just a block away! " [](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 10/10 Excellent "Will be Staying Here Again 😎" [](https://expedia.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg) ### River Hotel 10/10 Excellent "Clean room! Friendly and helpful staff. Room was small and the AC wouldn’t work. Staff gave me a fan that made it tolerable " [](https://expedia.com/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/f36e2ebe_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Staff were friendly. Place was clean. No issues. " [](https://expedia.com/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ## Find out more about Winnetka ## Winnetka B&B information | Number of reviews | 2,840 | | ----------------- | ------ | | Accommodation | 14 B&B | | Lowest Price | $95 | | Highest Price | $259 | ## 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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