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.
Level Chicago - River North
Downtown Chicago
Price was CA $1,134, price is now CA $858 per person
CA $858
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.
Reviewed on Jun 16, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,839, price is now CA $1,245 per person
CA $1,245
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.
Reviewed on Jun 16, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,235, price is now CA $1,664 per person
CA $1,664
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Fantastic, attentive staff. Beautiful facilities.
Reviewed on Jun 17, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Downtown Chicago
Price was CA $1,329, price is now CA $1,028 per person
CA $1,028
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.8/10 Excellent! (2,320 reviews)
The staff here is wonderful and helpful. Clean rooms, water stations on most floors.
Reviewed on Jun 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,891, price is now CA $1,482 per person
CA $1,482
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun
Reviewed on Jun 17, 2026
Winnetka Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jun 29 to Jun 30
CA $191
CA $227 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,295 reviews)
"Have to pay for parking plus the ac barely works"
Reviewed on Jun 17, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jul 5 to Jul 6
CA $223
CA $266 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,588 reviews)
"Amazing! My daughter and I loved it, including the location."
Reviewed on Jun 17, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jun 30 to Jul 1
CA $203
CA $231 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (2,685 reviews)
"Hotel is conveniently located nearby the Chicago O’Hare airport. The room was clean and amenities were good for our stay. Shuttle from the airport to the hotel was helpful."
Reviewed on Jun 17, 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.
Stay near popular Winnetka attractions
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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.
