Title: Winnetka Vacation Packages & Trips 2025/2026 from CA $756 | 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)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Winnetka Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

-   ## 
    
    Plan, book, travel with confidence
    

### 

Better together

Save up to CA $1,096 when you book a flight and hotel together\*

### 

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

### 

Rest easy

Plan, book, and manage your trip all in one place

#### Your Winnetka Vacation

When a city adventure is calling, answer it with a Winnetka vacation package. With all your travel needs in place before you leave, all you have to do here is focus on making unforgettable memories. Fill your free time with tours of [Chicago Botanic Garden](https://www.expedia.ca/Chicago-Botanic-Garden-Chicago.d6064029.Vacation-Attraction), [The Glen Club](https://www.expedia.ca/The-Glen-Club-Chicago.d6227490.Vacation-Attraction) and [North Shore Center for the Performing Arts](https://www.expedia.ca/North-Shore-Center-For-The-Performing-Arts-Chicago.d6152652.Vacation-Attraction), some of the attractions you simply have to see during your trip to Winnetka. Browse Expedia's wide range of travel options and begin planning your perfect vacation to Winnetka now.

## Top Winnetka Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $756

per person

Jan 16 - Jan 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,761 reviews)

The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.

Reviewed on Oct 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=vJpposegSqaEF0D5nI1JfyO5ciOIu7Xe9wBW5NNZU_WB-OTfaXHzstIJ5C3qE2ja)

![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Michigan Avenue Chicago

Downtown Chicago

CA $908

per person

Dec 21 - Dec 25

found 18 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

8.8/10 Excellent! (1,070 reviews)

Excellent staff all around. I will return.

Reviewed on Oct 25, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-25/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6KHyOZ2ExWUXVKX-LSTBh3LGYJlttsR0JZv2CZiqCPTw)

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $916

per person

Dec 29 - Jan 3

found 18 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (367 reviews)

Easy check-in, friendly staff, beautiful building with nice amenities.

Reviewed on Oct 27, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6HfS7vg0tK4jbTZsOYIWwCt3Ps2hX6UMKMORVrpQ1Jfa)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $799

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

We loved the Pendry!

Reviewed on Oct 27, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jf0DT4Lm6U9wjgn8OGicLyUXtBnmIhzxil_7vJs-G6LM9)

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $980

per person

Dec 27 - Jan 2

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (721 reviews)

The room was very clean and felt fresh on arrival. Shortly after check in and bringing my luggage upstairs, I was greeted at the door with fresh towels and blankets without even asking. At the door we requested additional pillows and notified the staff of a loose door handle. He helped us identify how to open the balcony door with the handle in its current state and also entered a ticket for it to e fixed in the mean time. He then returned with more items we asked for later. Great service and very helpful.

Reviewed on Oct 27, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=zDfec60NLqJEeYLnaVLFycqRa12-3DLASqNJ9hXNaPXau0hxoDgntecHl3cUacgg)

## Ready to book your vacation to Winnetka?

Choose your dates

## Winnetka Hotel Deals

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $177

CA $208 total

Nov 16 - Nov 17

includes taxes & fees

8.4/10 Very Good! (5,162 reviews)

We enjoyed our stay, great location for walking around downtown.

Reviewed on Oct 27, 2025

[](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=175751)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $131

CA $154 total

Nov 24 - Nov 25

includes taxes & fees

7.8/10 Good! (9,592 reviews)

From the moment we walked in the security was very friendly and helpful the first front desk attendant was amazing her name was Jasmine she was incredibly sweet helped us the best she could when we came back to do an early check-in the second person who helped us was incredibly rude service was terrible ...

Reviewed on Oct 26, 2025

[](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=175751)

![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Freehand Chicago

19 East Ohio Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $95

CA $137 total

Nov 26 - Nov 27

includes taxes & fees

7.8/10 Good! (2,508 reviews)

Very accessible location and amazing staff.

Reviewed on Oct 21, 2025

[](https://expedia.ca/Hotel-Search?startDate=26%2F11%2F2025&endDate=27%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=175751)

[See all 4,481 properties in Winnetka](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025&regionId=175751)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Winnetka

![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### What to do in Winnetka

![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Architecture River Tour

CA $68

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details)

![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Architecture Center River Cruise aboard First Lady

CA $78

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

[See all activities in Winnetka](https://expedia.ca/things-to-do/search?rid=175751)

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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## Go further with the Expedia app

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Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)