Wilmette Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
CA $808
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,983
per person
Sep 14 - Sep 17
just found
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on Aug 5, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

CA $1,063
per person
Oct 2 - Oct 6
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,686
per person
Sep 14 - Sep 17
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
CA $1,915
per person
Sep 14 - Sep 17
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.

Reviewed on Aug 8, 2026

Ready to book your vacation to Wilmette?

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Wilmette Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $212
CA $252 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (1,957 reviews)
"nice environment"

Reviewed on Aug 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $303
CA $356 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,462 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.

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.
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Wilmette Park District Swimming Beach

10.0/10 (2 reviews)
Why not spend a lazy afternoon at Wilmette Park District Swimming Beach during your trip to Wilmette? Visit the shops in this family-friendly area, or simply enjoy its restaurants.
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Langdon Park Beach

10.0/10 (1 review)
Why not spend a lazy afternoon at Langdon Park Beach during your trip to Wilmette? Visit the shops in this family-friendly area, or simply enjoy its restaurants.
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Wilmette Village Hall

You can take time to visit Wilmette Village Hall during your travels to Wilmette. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
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What to do in Wilmette

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $70
per adult
92% of travellers recommend
Chicago By Night River and Lake Cruise
See all activities in Wilmette

Frequently asked questions

How much does a Wilmette vacation package cost?
Offering great value package deals from CA $808 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.