
Winnetka Vacation Packages
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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.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $843, price is now CA $479 per person
CA $479
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean
Reviewed on Aug. 18, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,674, price is now CA $1,012 per person
CA $1,012
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025

Park Hyatt Chicago
Downtown Chicago
Price was CA $1,656, price is now CA $1,018 per person
CA $1,018
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,566, price is now CA $981 per person
CA $981
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!
Reviewed on Aug. 18, 2025
Winnetka Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 2 to Sep 3
CA $185
CA $218 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (8,961 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."
Reviewed on Aug. 17, 2025

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 1 to Sep 2
CA $208
CA $245 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,201 reviews)
"I asked for a microwave and they said they would bring it to the room and it was never delivered, other than that, the stay was very comfortable and convenient."
Reviewed on Aug. 18, 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is CA $222 per night from Sep 3 to Sep 4
CA $222
CA $260 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,711 reviews)
"Happy Hour drinks were amazing!"
Reviewed on Aug. 16, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.