Shorewood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing amenities. friendly staff and clean rooms. Views from the balcony were so nice!

Reviewed on Jul. 12, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Ready to book your vacation to Shorewood?

 

Choose your dates

Shorewood Hotel Deals

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 $114 per night from Jul 20 to Jul 21
CA $114
CA $126 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (1,021 reviews)
"Location, comfort of room"

Reviewed on Jul. 12, 2025

DoubleTree by Hilton Lisle Naperville
Motel 6 Naperville, IL
Motel 6 Naperville, IL
2 out of 5
1585 Naperville Wheaton Road, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $72 per night from Jul 15 to Jul 16
CA $72
CA $80 total
Jul 15 - Jul 16
includes taxes & fees
7.8/10 Good! (1,019 reviews)
"Clean and well maintained"

Reviewed on Jul. 12, 2025

Motel 6 Naperville, IL
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 $134 per night from Jul 15 to Jul 16
CA $134
CA $176 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very Good! (1,163 reviews)
Could of been better.
"When we checked in we where given a pool suite. Before we put anything in the room we inspected it and pool was dirty so we went ttro office thwy shiwed us another one which was cleaner but the place needs a ton of uogra3des one being mattresses"

Reviewed on Jul. 13, 2025

The Champagne Lodge & Luxury Suites
See all 368 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

Frequently asked questions

How much does a Shorewood vacation package cost?
You can snap up a vacation package to this destination from CA $688 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.