Title: Winnetka Condo Rentals from CA $279 | Expedia.ca [Winnetka Travel Guide](https://expedia.ca/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.ca/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Vacation Rentals in Winnetka](https://expedia.ca/Winnetka-Vacation-Rentals.d175751.Travel-Guide-VacationRentals)[Flights to Winnetka](https://expedia.ca/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Winnetka Car Rentals](https://expedia.ca/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.ca/Winnetka.d175751.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Winnetka from CA $279 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winnetka Condo Rentals ![Exterior detail](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/a067dc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/1e525a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/e7806e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/04e27943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Urban Retreat Near Wrigley Field w/Parking Lakeview 10/10 Exceptional (37) "The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area." CA $208 CA $628 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/e55ec92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/d31f0f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/646b6706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/25e124e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants Downtown Chicago 10/10 Exceptional (2) "I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again." [](https://www.expedia.ca/Chicago-Hotels-Chicago-Gold-Coast-Luxury-Penthouse-4-BDR-3-BR-Massive-Rooftop-Views.h112528246.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/e3a1a561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/2a46ff05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/fd9d2968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/efc73b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3BRCondo near Wrigley/Dtwn +FreeParking Lincoln Park 9.6/10 Exceptional (45) "It was a great place to stay and very spacious!" [](https://www.expedia.ca/Chicago-Hotels-Spacious-3BRCondo-Near-WrigleyDtwn-FreeParking.h83596157.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78460000/78459600/78459583/bd22ff60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/79000000/78460000/78459600/78459583/0ea3b3a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78460000/78459600/78459583/6d12f8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78460000/78459600/78459583/a28f965d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR Modern Condo near Wrigley/Dwtn +Free Parking Lincoln Park 9.6/10 Exceptional (39) "3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! " CA $425 CA $913 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Chicago-Hotels-3BR-Modern-Condo-Near-WrigleyDwtn-Free-Parking.h78459583.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78130000/78127200/78127193/7887bfb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78130000/78127200/78127193/e426462d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78130000/78127200/78127193/022ffc6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78130000/78127200/78127193/9d75be77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 3 BR in prime Chicago location Lincoln Park 9.8/10 Exceptional (115) "Great location within walking distance to Wrigley Field and countless restaurants. " [](https://www.expedia.ca/Chicago-Hotels-Stunning-3-BR-In-Prime-Chicago-Location.h78127193.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101930000/101926700/101926653/1cb7e17b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101930000/101926700/101926653/4e056ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101930000/101926700/101926653/0b7257e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/102000000/101930000/101926700/101926653/4b24e0fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 3BR River North Condo - Free Parking Downtown Chicago 10/10 Exceptional (23) "House was very accommodating and well stocked for a family of 4 including two teenage children. Check in was easy and as described, and location was easy walking distance to restaurants and shopping. Would definitely stay here again when in Chicago!" [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-3BR-River-North-Condo-Free-Parking.h101926653.Hotel-Information) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/34000000/33550000/33548200/33548184/3d713b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548200/33548184/a761e8a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33548200/33548184/09b993fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33550000/33548200/33548184/58fff569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field Lakeview 10/10 Exceptional (108) "This was a great house, location, host....made our weekend easy and enjoyable!!" [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Condo.h33548184.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/90000000/89850000/89841200/89841164/w1788h1188x0y2-67128702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89850000/89841200/89841164/d78f2ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89850000/89841200/89841164/b97cbb29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89850000/89841200/89841164/97d618ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elizabeth by Coast to Cactus | Chic Artists Loft Downtown Chicago 9.2/10 Wonderful (22) "Great place, excellent location and close to the trains!!!!" [](https://www.expedia.ca/Chicago-Hotels-Elizabeth-By-Coast-To-Cactus-Chic-Artists-Loft.h89841164.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/5bb478a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/e0567df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/870fb3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/f8b770f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Suite/Mins to L Train /Laundry/Free Parking Oak Park 9.6/10 Exceptional (54) "Good location. " CA $98 CA $279 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Chicago-Hotels-Chic-SuiteMins-To-L-Train-LaundryFree-Parking.h83570994.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/100000000/99250000/99244100/99244065/w1217h775x1y0-a2307bf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/100000000/99250000/99244100/99244065/w1225h819x0y0-e156103e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99250000/99244100/99244065/77bb5a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99250000/99244100/99244065/ebd32982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious, Clean and Steps from Wrigley Field! Lakeview 9.8/10 Exceptional (22) "Great location, clean and spacious. A little loud with the train close by but added to the Chicago experience! " [](https://www.expedia.ca/Chicago-Hotels-Spacious.h99244065.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82810000/82802900/82802822/f01a9cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/83000000/82810000/82802900/82802822/beabb848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82810000/82802900/82802822/6d70ffa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82810000/82802900/82802822/bb5796c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood West Ridge 8.6/10 Excellent (19) "This place was clean and host was very nice" [](https://www.expedia.ca/Chicago-Hotels-For-Up-To-6-Spacious-Lovely-Chicago-Style-3-BDR-Condo-Safe-Quiet-Neighborhood.h82802822.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87690000/87684800/87684787/0afb39d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87690000/87684800/87684787/a1d50ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87690000/87684800/87684787/570057cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87690000/87684800/87684787/eefa87df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Chicago living near United Center Austin 8.8/10 Excellent (20) "Immaculately clean property" [](https://www.expedia.ca/Chicago-Hotels-Experience-Chicago-Living-NearUnited-Center.h87684787.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63890000/63882800/63882759/de8b2ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63890000/63882800/63882759/d502ea21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63890000/63882800/63882759/d854c255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63890000/63882800/63882759/69f296dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW LUXURY CONDO WITH PATIO DECK West Town 10/10 Exceptional (181) "Wonderful place to stay. We would stay there again. " [](https://www.expedia.ca/Chicago-Hotels-NEW-LUXURY-CONDO-WITH-PATIO-DECK.h63882759.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83460000/83455900/83455869/57ada61d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83460000/83455900/83455869/b342ae08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83460000/83455900/83455869/ceb4fca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/84000000/83460000/83455900/83455869/47536cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Chicago living near United Center Austin 9.2/10 Wonderful (26) "Plenty of room, very nice amenities, short walk to bus line. Felt great coming back every day to that rather than a hotel room. Much more personal." [](https://www.expedia.ca/Chicago-Hotels-Clean-Cozy-Entire-3-Bedroom-Unit-7-Miles-From-Downtown.h83455869.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499053/6e7ba948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499053/7b8df7b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499053/2f7eea1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499053/4ec00895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Inn - Unit 3 Lakeview 10/10 Exceptional (42) "The property was perfect for our stay. Easy walk to baseball and food options were great." [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Inn-Unit-3.h92499053.Hotel-Information) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/91000000/90990000/90982200/90982135/1c3f75fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/91000000/90990000/90982200/90982135/37669387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90990000/90982200/90982135/c7daa883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90990000/90982200/90982135/31c4b515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Exclusive- 7 Bed, 6 Bath Retreat Logan Square 9.6/10 Exceptional (19) "Adam's building was the perfect space for our team offsite in Chicago. Very centrally located with the best coffee in the city downstairs! Would definitely stay here again." [](https://www.expedia.ca/Chicago-Hotels-The-Exclusive-7-Bed.h90982135.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499045/f2ebfeef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499045/d6c5f1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499045/fd1a0236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/93000000/92500000/92499100/92499045/42250be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Inn - Unit 2 Lakeview 10/10 Exceptional (14) "Great VRBO! So clean and nice. Will definitely be back!" [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Inn-Unit-2.h92499045.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/e173d9a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/4959ccd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/3b41a424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, memory foam beds, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/b3492081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW LUXURY PENTHOUSE CONDO West Town 10/10 Exceptional (192) "I cannot recommend this property enough! Easiest check-in/out ever. Excellent communication from the host. And the condo itself was fabulous! The area was so quiet and peaceful, it was hard to believe we were in a city the size of Chicago. Having a lot private garage was" [](https://www.expedia.ca/Chicago-Hotels-NEW-LUXURY-PENTHOUSE-CONDO.h63358275.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22864700/22864683/14ea02c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22864700/22864683/8a8f698a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22870000/22864700/22864683/8c542b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22864700/22864683/4bf204a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walking distance to restaurants, shops and Lake Michigan, Rogers Park 9.6/10 Exceptional (184) "We had a great time and the property manager was very thoughtful. It was a very cute apartment and great location very close to Loyola." [](https://www.expedia.ca/Chicago-Hotels-Walking-Distance-To-Restaurants.h22864683.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116550000/116548100/116548056/f1df153a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116550000/116548100/116548056/9acd73f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116550000/116548100/116548056/e4c1407a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116550000/116548100/116548056/b380663c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fun Downtown Penthouse #3 | Vintage +balcony&gym Downtown Chicago 9.6/10 Exceptional (14) "We went to Chicago for baseball and sightseeing, 4 nights. This place was everything it was represented to be—spacious, very comfortable and well furnished. The location is close to the L and bus lines which made it very convenient for us to get around. Owners checked in with us periodically during our stay and were highly responsive before, during and after the trip. We would definitely return here on a next trip. " [](https://www.expedia.ca/Chicago-Hotels-Fun-Downtown-Penthouse-3-Vintage-Balconygym.h116548056.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.ca/Hotel-Search?startDate=2025-10-08&endDate=2025-10-09®ionId=175751&adults=2&lodging=CONDO&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Condos.d175751-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Condos.d175751-aaCondos.Travel-Guide-Accommodation) ## Top Winnetka Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Grea5" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Would highly recommend this hotel. Very clean, great happy hour and awesome breakfast! Rooms are very comfortable and quiet" [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Good room. Good location to train. Area is a little suspect" [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "I loved this hotel, I really enjoyed staying there, it was a very convenient area it's close to everything. I would definitely stay there again. Thank you" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "perfect" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "We really enjoyed staying at the Whitehall during our Chicago visit. From the moment we stepped in, we were warmly welcomed by the staff. The room was large,clean,and the air conditioning worked great. The breakfast area was lovely and had plenty of great varieties to choose from. The location was top notch and on a quieter street. My only complaint is that the wifi connection is poor. We will likely stay again." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "This is my third time at this hotel . Staff are so nice . Front of house, Jordan’s attention to detail in assisting me with a special request while i was here was next level . I will be back . " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "I thoroughly enjoyed my stay at the Chicago Hilton. Loved the ambiance and the inspiring architecture on entering and the old fashioned elevator lobby was a treat itself. The Irish Pub was outstanding with a nice atmosphere and not overly sports oriented like some. I was there during some kind of trade event but the place never felt crowded or had long waits for anything. My room on the 18th floor was a little spartan for my liking, though quite large, however for the amount spent I expected more. Had a nice view and was quiet enough so I’m not taking points away, but yes - a room update is past due if other rooms were like mine. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![River Hotel](//images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Perfect for a quick weekend trip! " [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ## Find out more about Winnetka ## Winnetka Condo Rentals information | Number of reviews | 1,134 | | --- | --- | | Accommodation | 243 Condo Rentals | | Lowest Price | CA $279 | | Highest Price | CA $913 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in Glenview](https://www.expedia.ca/5Star-Glenview-Hotels.s50-0-d8006.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Gross Point](https://www.expedia.ca/5Star-Gross-Point-Chicago-Hotels.s50-n6132100-0.Travel-Guide-Filter-Hotels) - [Hotels near Baha'i House of Worship](https://www.expedia.ca/Bahai-House-Of-Worship-Hotels.0-l6152644-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Botanic Garden](https://www.expedia.ca/Chicago-Botanic-Garden-Hotels.0-l6064029-0.Travel-Guide-Filter-Hotels) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Evanston Central Street Station](https://www.expedia.ca/Evanston-Central-Street-Station-Hotels.d6214761.Travel-Guide-Hotels) - 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