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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,142, price is now CA $755 per person
CA $755
per person
Jul 1 - Jul 5
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,787, price is now CA $1,125 per person
CA $1,125
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on Apr 25, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,383, price is now CA $889 per person
CA $889
per person
Jun 5 - Jun 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (480 reviews)
The staff was friendly and the bed was very comfortable! Easy to find parking, many food options within walking distance.

Reviewed on Apr 21, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,447, price is now CA $941 per person
CA $941
per person
Jul 1 - Jul 5
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,873, price is now CA $1,261 per person
CA $1,261
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (466 reviews)
Great spot for small families that may need a space for than just sleeping

Reviewed on Apr 27, 2026

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Winnetka Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 26 to May 27
CA $118
CA $182 total
May 26 - May 27
includes taxes & fees
8.2/10 Very Good! (2,655 reviews)
It was ok

Reviewed on Apr 28, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $173 per night from May 25 to May 26
CA $173
CA $205 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,143 reviews)
Everything was great until morning then our room filled up with smoke otherwise it was good

Reviewed on Apr 27, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 25 to May 26
CA $134
CA $160 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,472 reviews)
Quite. Clean, Safe

Reviewed on Apr 27, 2026

Club Quarters Hotel, Central Loop, Chicago
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winnetka

Wrigley Field

Wrigley Field

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

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

Naval Base Great Lakes

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

What to do in Winnetka

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Winnetka

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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.