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.
Baymont by Wyndham Glenview
Price was CA $768, price is now CA $557 per person
CA $557
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,004 reviews)
Breakfast was there but not a lot
Look at moving in individuals using it as a home
Good location though nice area around the place
Reviewed on May 9, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $2,632, price is now CA $1,645 per person
CA $1,645
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.
Reviewed on May 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
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
Pendry Chicago
Downtown Chicago
Price was CA $1,700, price is now CA $1,206 per person
CA $1,206
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,874, price is now CA $1,364 per person
CA $1,364
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Beautiful property. Convenient location for anything in the Loop area. Love the coffee and wine hours. Great restaurant in Boleo, too!
Reviewed on May 5, 2026
Winnetka Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from May 12 to May 13
CA $183
CA $217 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (10,207 reviews)
Clean room, good staff
Reviewed on May 11, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from May 25 to May 26
CA $193
CA $269 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,106 reviews)
Was a really nice hotel. My only concerns was the phones in the room didn’t work. No way to call front desk, front people weren’t super helpful and there was no microwave. Rooftop bar and room were excellent
Reviewed on May 10, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 25 to May 26
CA $178
CA $212 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,293 reviews)
The hotel staff is excellent! Very friendly and very helpful. The hotel is very clean and well maintained. The only issue I had was the charging ports and electrical sockets next to our bed did not work which made overnight charging of our phones and watches difficult.
Reviewed on May 10, 2026
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.
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
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
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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.
