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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,068, price is now CA $756 per person
CA $756
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

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 $1,284, price is now CA $938 per person
CA $938
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Everything was nice. The room was clean and a nice size but it’s the views that make it worthwhile! Waking up & seeing the beautiful sunrise over the lake was amazing!!

Reviewed on Nov 11, 2026

Ready to book your vacation to Wilmette?

 

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Wilmette Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Nov 26 to Nov 27
CA $164
CA $195 total
Nov 26 - Nov 27
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Dec 7 to Dec 8
CA $164
CA $195 total
Dec 7 - Dec 8
includes taxes & fees
8/10 Very good! (2,697 reviews)
"Excellent stay! Will definitely seek this property out again for my stay in Chicago"

Reviewed on Nov 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $144 per night from Nov 23 to Nov 24
CA $144
CA $171 total
Nov 23 - Nov 24
includes taxes & fees
River Hotel
See all 4,376 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
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Stay near popular Wilmette attractions

Baha'i House of Worship

8.0/10 (5 reviews)
On the peaceful shores of Lake Michigan, this elaborate temple, open to all, exudes a sense of peace that makes it a welcome change from Chicago’s bustle.
See properties

What to do in Wilmette

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Wilmette

Frequently asked questions

How much does a Wilmette vacation package cost?
Offering great value package deals from CA $671 on Expedia, you'll be thrilled with how little a vacation to Wilmette costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Wilmette?
You can usually find reduced prices and greater availability in January, February and April. Check out our cheap Wilmette vacation packages and you could land some great off-season deals.
How many days is enough for Wilmette?
We'd suggest booking a Wilmette vacation for around 3 days. This gives you plenty of time to tick off top attractions such as Grosse Point Lighthouse and Ryan Field, and also explore neighbourhoods like Rogers Park and North Park. You could even make time for a day trip or two outside of Wilmette.
Is it worth booking a vacation package to Wilmette?
Well known for its walking trails and home to leading attractions like Baha'i House of Worship, a Wilmette vacation is sure to impress. Another highlight to check out? Don't miss Langdon Park Beach.
How to find the best Wilmette package deals?
Bagging a cheap Wilmette package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Wilmette package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Wilmette vacation as a package?
You can enjoy significant savings on your Wilmette retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Wilmette?
If you're planning a spur-of-the-moment Wilmette adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Wilmette?

  1. Choose your dates: What you plan to do in Wilmette and your preferred season will help you decide when to get away.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to set aside for your trip to Wilmette. Then, pick a hotel that works with your budget, whether that's a low-cost stay or a swankier getaway.
  3. Decide how long to go away for: Now that you know more about Wilmette, you can work out the right length of your break. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Wilmette vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.