Wilmette Vacation Packages

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Your Wilmette Vacation

Pick a Wilmette vacation package and focus on what counts — having some fun. This means no more planning stresses, just a lot more time to savor what's special about this lively city, such as its rich history and coastal scenery. Make your trip to Wilmette even more exciting by including some sightseeing. The Glen Club, North Shore Center for the Performing Arts and The Glen Town Center are some of the most popular attractions you'll want to explore. Don't delay exploring this city any longer. Your perfect Wilmette vacation is a few quick clicks away with Expedia.

Top Wilmette Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,522, price is now CA $1,031 per person
CA $1,031
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on May 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,631, price is now CA $1,093 per person
CA $1,093
per person
Jun 28 - Jul 3
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,957, price is now CA $1,353 per person
CA $1,353
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Love the amenities. Great location too

Reviewed on May 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,714, price is now CA $1,207 per person
CA $1,207
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,548, price is now CA $1,099 per person
CA $1,099
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

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Wilmette Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is CA $183 per night from May 27 to May 28
CA $183
CA $217 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.

Reviewed on May 12, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
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! (4,123 reviews)
We had a great stay for our anniversary trip!

Reviewed on May 12, 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
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! (4,302 reviews)
Staff was helpful and friendly. The rooms were clean and spacious!

Reviewed on May 12, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,612 properties in Wilmette
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 Wilmette

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

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

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

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

Navy Pier

What to do in Wilmette

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 Wilmette

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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.