Riverwoods Vacation Packages

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Top Holiday Package Deals in Riverwoods

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was CA $1,002, price is now CA $655 per person
CA $655
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,890 reviews)
Gorgeous lobby. Wonderful dining options.

Reviewed on Aug. 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $820 per person
CA $820
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,190, price is now CA $1,400 per person
CA $1,400
per person
Oct 3 - Oct 8
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug. 22, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,133, price is now CA $740 per person
CA $740
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent

Reviewed on Aug. 21, 2025

Where to stay in Riverwoods

Find the best Riverwoods areas and neighborhoods for the activities you enjoy most. Learn more about Riverwoods
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Riverwoods Hotel Deals

Holiday Inn Express & Suites Chicago-Deerfield/Lincolnshire by IHG

Holiday Inn Express & Suites Chicago-Deerfield/Lincolnshire by IHG

2.5 out of 5
2600 Lake Cook Rd, Deerfield, IL
Fully refundable
The price is CA $137 per night from Sep 5 to Sep 6
CA $137
CA $153 total
Sep 5 - Sep 6
includes taxes & fees
Holiday Inn Express & Suites Chicago-Deerfield/Lincolnshire by IHG
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is CA $209 per night from Sep 19 to Sep 20
CA $209
CA $245 total
Sep 19 - Sep 20
includes taxes & fees
Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 19 to Sep 20
CA $246
CA $289 total
Sep 19 - Sep 20
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 1,745 properties in Riverwoods
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 Riverwoods vacation package cost?
Cross off another part of the world with our Riverwoods vacation packages, which start from just CA $655. Choose the flights and hotels that suit your plans. Then, add on some activities or tours for an unforgettable escape.
How do I get a cheap travel package to Riverwoods?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got it all. Pick the combination that suits your style and see your savings pile up. We know a travel package is never a one-size-fits-all. That's why Expedia offers over 550 airlines and 1,000,000 hotels around the globe, which lets you customize your Riverwoods adventure.
Where should I stay in Riverwoods?
With so much to do in Riverwoods, it makes sense to secure a room in a hotel near its attractions. Trinity International University, Par-King Skill Golf and Edward L. Ryerson Conservation Area are some popular ones to put on your to-do list.
What are the top hotels in Riverwoods?
If it's comfort and convenience you want, you can't beat Holiday Inn Express & Suites Chicago-Deerfield/Lincoln, an IHG Hotel. Spend your evenings unwinding here and your days exploring Riverwoods's best attractions.
How far in advance should I book my Riverwoods vacation?
To bag rock-bottom prices, book ASAP. Air carriers typically release flights, along with some of the lowest fares, up to 12 months ahead of time. Hotels, car rental and activities should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in Riverwoods, there are always lots of great deals on Expedia. Book something in today!
What does an Expedia Riverwoods travel package include?
It depends on what sort of escape you're planning. Riverwoods vacation deals can include flights, hotels and car rentals. You can mix and match to create the bundle that suits you. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Riverwoods travel package?
Find deals that suit your budget with an Expedia package. Airfares, hotels, rental cars — we've got them all. You'll save precious dollars just by combining your bookings. Whether you're taking off on a ski trip or sipping cocktails on a beach, your ideal getaway is just a few clicks away.
Can I choose my airline with a Riverwoods Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Riverwoods vacation package?
We totally get that unexpected stuff happens. If you've locked in a Riverwoods vacation package and need to cancel or amend it, we're here to help. We recommend checking out our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it's more than 24 hours, your hotel, airline or car rental company may impose a fee.

Discover the most popular places to visit in Riverwoods

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.