Name: River Hotel
Price range: CA $208
Rating: 8.8

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, The Glen Club and North Shore Center for the Performing Arts, 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.

Level Chicago Fulton Market

Downtown Chicago

CA $1,072

per person

Jun 26 - Jun 30

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (471 reviews)

The rooms were very clean!

Reviewed on May 4, 2026

Swissotel - Chicago

Downtown Chicago

CA $1,608

per person

Jul 30 - Aug 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,303 reviews)

Picked the hotel because it was supposed to be near Riviera theater. It really wasn't. Otherwise, it's a beautiful property. Staff are friendly and helpful. There's casual and fine dining at the location. Easy to get a cab if you don't have an app. Across from riverfront.

Reviewed on May 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $2,155

per person

Jul 30 - Aug 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,489 reviews)

If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,940

per person

Jul 30 - Aug 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,670 reviews)

Great property and location!

Reviewed on May 8, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $1,541

per person

Jul 30 - Aug 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very Good! (2,655 reviews)

If you’re up for walking, this hotel is a great place to stay close enough to most things.

Reviewed on May 8, 2026

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Winnetka Hotel Deals

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL

Fully refundableReserve now, pay when you stay

CA $238

CA $325 total

Jun 10 - Jun 11

includes taxes & fees

8.2/10 Very Good! (2,697 reviews)

great location

Reviewed on May 9, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $183

CA $217 total

May 11 - May 12

includes taxes & fees

8/10 Very Good! (10,193 reviews)

Clean and very old

Reviewed on May 9, 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

CA $208

CA $247 total

May 26 - May 27

includes taxes & fees

8.8/10 Excellent! (5,192 reviews)

I can only review the staff at The River Hotel is AMAZING to say the least. From the moment I walked through the door I felt at home. I received a warm welcome and a fabulous room with all of the amenities. My room (suite) was spacious, clean and so comfortable. The hotel is centrally located so ...

Reviewed on May 9, 2026

See all 4,558 properties in Winnetka

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.

Discover the most popular places to visit in Winnetka

Wrigley Field

4.5/5(159 reviews)

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

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier

4.5/5(460 reviews)

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

What to do in Winnetka

360 CHICAGO Observation Deck

CA $37

per adult

88% of travellers recommend

Art Institute of Chicago

CA $55

per adult

94% of travellers recommend

Skydeck - Willis Tower Admission

CA $61

per adult

96% of travellers recommend

See all activities in Winnetka

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Your Winnetka Vacation

Top Winnetka Vacation Deals

Level Chicago Fulton Market

Swissotel - Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Hotel Felix River North/Magnificent Mile

Ready to book your vacation to Winnetka?

Winnetka Hotel Deals

Hotel Felix River North/Magnificent Mile

Congress Plaza Hotel

River Hotel

Discover the most popular places to visit in Winnetka

Wrigley Field

Naval Base Great Lakes

Navy Pier

What to do in Winnetka

360 CHICAGO Observation Deck

Art Institute of Chicago

Skydeck - Willis Tower Admission

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