Title: Winnetka Villas from CA $95 | 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)

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# Search Winnetka Villa Rentals from CA $95

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## Check prices for these dates

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Winnetka

![Signature Penthouse, 2 Bedrooms, 2 Bathrooms, City View | City view](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/7164fbba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freehand Chicago

[](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

Downtown Chicago

8.0/10

Very good

(2649)

"The room was spotless and the staff where great!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maria

CA $76

CA $114 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(2967)

"Great location and great staff!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

lynne

CA $105

CA $123 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(2986)

"Great rooms, love the bar and amazing breakfast!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

CA $137

CA $200 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Hotel

[](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(4861)

"Great location, comfortable room, and nice staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Claudia

CA $101

CA $118 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![City view](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/da561c89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Warwick Allerton - Chicago

[](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(3018)

"Enjoyed this hotel stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly

CA $87

CA $143 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Snack bar](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/4844f60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast and dinner served](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/81d45e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/0afe31db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/w1584h1367x232y0-cd23229b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cambria Hotel Chicago Loop - Theatre District

[](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(1462)

"Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Megan

CA $120

CA $141 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/be69fa71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/db08811d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/71356b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Embassy Suites by Hilton Chicago Downtown Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(2750)

"Excellent place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Teniesha

CA $102

CA $161 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/7153c023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

[](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(2266)

"Great staff and restaurants!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Abigale

CA $128

CA $197 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Suite, 1 King Bed, Lake View, Lakeside](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Congress Plaza Hotel

[](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

Downtown Chicago

8.0/10

Very good

(9667)

"Wonderful stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Zach

CA $129

CA $152 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitehall Hotel, BW Premier Collection

[](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(3801)

"Comfortable Room, great location and Excellent Staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles

CA $105

CA $124 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/2489547a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/17f1a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/63f719c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 1 King Bed (Smoke Free)](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/e4287551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Saint Clair- Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-The-St-Clair-Hotel-Magnificent-Mile.h49985.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(1787)

"Great stay in a great area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Giselle

CA $92

CA $110 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Chicago-Hotels-The-St-Clair-Hotel-Magnificent-Mile.h49985.Hotel-Information)

![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eurostars Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(3163)

"Amazing stay very clean and beautiful views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deigo

CA $132

CA $155 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago/Magnificent Mile Suites

[](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(3498)

"Great place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

RaShawna

CA $112

CA $131 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/d4307099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/74cf409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/c5202ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Club Quarters Hotel Wacker at Michigan, Chicago

[](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(1989)

"A good place for stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julio

CA $102

CA $119 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/c12c78f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/w3576h2561x0y0-5f9110d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric The Loop Chicago

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(2305)

"Very nice clean hotel! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jodee

CA $159

CA $186 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/cbeee5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/9ab0dcf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/0c9aebe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/2b6118c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FOUND Hotel Chicago River North

[](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(376)

"Good place, good location, friendly staff and a great bar! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Georgi

CA $81

CA $95 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/fe59f9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/6dc8c836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown South Loop

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(1762)

"Great check in and responsive front desk staff. Housekeeping staff did a great job during our visit! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steven

CA $98

CA $115 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information)

![Nightclub](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/0120c0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/a9bc446d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/9378ca8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Club Quarters Hotel, Central Loop, Chicago

[](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(3317)

"Great hotel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anthony

CA $100

CA $117 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information)

![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/10b6347e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c804195a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/6d294877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silversmith Hotel Chicago Downtown

[](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(2133)

"Hotel is beautiful, staff was very kind. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lauren

CA $111

CA $173 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2556x3y3-aad44a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/968cca43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fusion cuisine](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/e4e05f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Claridge House Chicago, Tapestry Collection by Hilton

[](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(1486)

"I really liked this location - we will stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lynnsey

CA $95

CA $152 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.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.

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## 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

"Room was comfortable and clean. Staff was very friendly "

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Very nice hotel"

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.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

"The room was very spacious, the hotel lobby and bar are beautiful. Staff is super friendly and helpful! Would definitely stay here again"

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Loved the location and the room was nice with a view!"

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Hotel was very nice. Clean and quiet rooms. Good value for the price. Staff was super friendly and overly accommodating during our stay. From the curb service upon arrival, the maintenance man that had to make a minor repair in our room to the bellman that waited at the curb with us to load our bags in the uber. Cannot recommend this hotel enough!"

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Very clean and the staff was wonderful!"

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"Beautiful old hotel convenient to downtown . Wonderful rooms and great onsite dining. You can hear the trains outside from pretty much every room but I found it acceptable noise level. "

[](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"Great hotel "

[](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"The room view was beautiful! The staff was super attentive and helpful. "

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

## Find out more about Winnetka

## Winnetka Villas information

| Number of reviews | 58,053   |
| ----------------- | -------- |
| Accommodation     | 5 Villas |
| Lowest Price      | CA $95   |
| Highest Price     | CA $200  |

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