Shorewood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Shorewood Vacation

Take away the hard part of planning your next great adventure with a Shorewood vacation package. Whether you're lured here by its food, history, art or something else, there's a never-ending supply of new experiences to be had. Can't wait to see the sights? Spend some time exploring leading attractions like Mistwood Golf Club during your trip to Shorewood. A few quick clicks is all it takes to create your ideal Shorewood vacation on Expedia.

Top Shorewood Vacation Deals

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 12 hours 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

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,394, price is now CA $992 per person
CA $992
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,039, price is now CA $1,462 per person
CA $1,462
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,001, price is now CA $2,200 per person
CA $2,200
per person
Dec 16 - Dec 21
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Very good service

Reviewed on Nov 9, 2026

Ready to book your vacation to Shorewood?

 

Choose your dates

Shorewood Hotel Deals

Hollywood Casino Aurora

Hollywood Casino Aurora

2 out of 5
2500 N Farnsworth Ave Aurora IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Nov 22 to Nov 23
CA $168
CA $212 total
Nov 22 - Nov 23
includes taxes & fees
Hollywood Casino Aurora
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
The price is CA $167 per night from Dec 10 to Dec 11
CA $167
CA $212 total
Dec 10 - Dec 11
includes taxes & fees
The Champagne Lodge & Luxury Suites
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Nov 15 to Nov 16
CA $155
CA $172 total
Nov 15 - Nov 16
includes taxes & fees
7.8/10 Good! (1,489 reviews)
"All was good"

Reviewed on Nov 9, 2026

DoubleTree by Hilton Lisle Naperville
See all 390 properties in Shorewood
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

Stay near popular Shorewood attractions

West Shore Park

After visiting West Shore Park, make a plan to see the other sights and activities in Shorewood. Amble around the area's forest or visit its shops.
See properties

Frequently asked questions

How much does a Shorewood vacation package cost?
You can snap up a vacation package to this destination from CA $983 on Expedia. However, how much your vacation to Shorewood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Shorewood?
To score cheap Shorewood vacation packages, organize your trip outside of peak periods like public holidays and major events. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Shorewood?
With a well-planned itinerary, you can easily hit the most popular Shorewood attractions in a handful of days. But if you prefer to discover hidden gems or go on day tours, consider booking your Shorewood vacation for longer.
How to find the best Shorewood package deals?
Use Expedia's handy filters to help you find some fabulous Shorewood package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Shorewood package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Shorewood vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights individually. Better still, you can personalize your Shorewood getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Shorewood?
If you have your Shorewood vacation dates locked in, book as soon as you can to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Shorewood?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Shorewood.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Shorewood.
  3. Decide your trip length: Consider how long you'd like to spend discovering Shorewood. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Shorewood 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.