Shorewood Vacations from $725

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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.

The Latest Shorewood vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,234, price is now $725 per person
$725
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.

Reviewed on Aug 23, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $2,051, price is now $1,060 per person
$1,060
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Exceptional hotel with ideal location and nice services.

Reviewed on Aug 23, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,668, price is now $1,492 per person
$1,492
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug 19, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,750, price is now $992 per person
$992
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
We love it here! Carissa (Chris?) the bellman is soo kind and professional.

Reviewed on Aug 23, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,880, price is now $1,100 per person
$1,100
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on Aug 20, 2025

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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
$83 nightly
The price is $92 total per night from Aug 31 to Sep 1
$92 total
Aug 31 - Sep 1
Total with taxes and fees
7.8/10 Good! (1,096 reviews)
"This was a horrible experience. The bedding was dirty and stained.. basically used. They provided a new room which smelled so bad we had to check out . The smell made my eyes & throat hurt and my daughter was getting a headache from the smell. We checked out and left the hotel. They said they would ..."

Reviewed on Aug 19, 2025

DoubleTree by Hilton Lisle Naperville
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
$122 nightly
The price is $128 total per night from Aug 25 to Aug 26
$128 total
Aug 25 - Aug 26
Total with taxes and fees
8.4/10 Very Good! (1,209 reviews)
"Extremely clean and wonderful rooms"

Reviewed on Aug 23, 2025

The Champagne Lodge & Luxury Suites
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
$55 nightly
The price is $61 total per night from Sep 14 to Sep 15
$61 total
Sep 14 - Sep 15
Total with taxes and fees
7.8/10 Good! (1,027 reviews)
"Not bad at all."

Reviewed on Aug 22, 2025

Motel 6 Naperville, IL
See all 369 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.

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Frequently asked questions

How much does a Shorewood vacation package cost?
Offering great value package deals from $725 on Expedia, you'll be thrilled with how little a vacation to Shorewood costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Shorewood?
December, January and February are the best times to look for cheap Shorewood vacation packages. Opting to travel in quieter periods means you can usually find better prices on accommodations and flights.
How many days is enough for Shorewood?
The ideal length for your Shorewood vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to tick off all the major sights and explore some hidden treasures along the way.
How to find the best Shorewood package deals?
Use Expedia's filter tool to help you find some of the best 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're looking to save, plan your break for midweek, or search for Shorewood package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Shorewood vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels separately. Better still, you can tailor your Shorewood trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Shorewood?
If you have your Shorewood vacation dates finalized, book as soon as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Shorewood vacation packages?
Your Shorewood trip should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.