Riverwoods Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Top Holiday Package Deals in Riverwoods

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,645, price is now CA $1,053 per person
CA $1,053
per person
Jun 11 - Jun 15
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on Apr 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,916, price is now CA $1,246 per person
CA $1,246
per person
Jun 11 - Jun 15
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .

Reviewed on Apr 17, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,845, price is now CA $1,229 per person
CA $1,229
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,120 reviews)
The anti hero beer,the doorman,staff,the comfortable bed, shower 🚿,

Reviewed on Apr 18, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,268, price is now CA $1,580 per person
CA $1,580
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on Apr 7, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,622, price is now CA $1,830 per person
CA $1,830
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
Celebrate my birthday here and upon arrival was given champagne. It made my evening even better. I felt at home will be returning

Reviewed on Apr 18, 2026

Where to stay in Riverwoods

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

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

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 $341 per night from May 9 to May 10
CA $341
CA $400 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,265 reviews)
The room was spotless and the concierge service was excellent.

Reviewed on Apr 17, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $208 per night from Apr 26 to Apr 27
CA $208
CA $237 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (2,497 reviews)
Very convenient for travelers arriving late at O’Hare. The shuttle drivers are friendly and helpful, which makes a stressful travel day much easier. With flight delays becoming the “new normal” at ORD, staying near the airport on the first night is a practical solution. The hotel also offers excellent ...

Reviewed on Apr 18, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from May 2 to May 3
CA $258
CA $302 total
May 2 - May 3
includes taxes & fees
8.6/10 Excellent! (1,237 reviews)
Everyone was so helpful in the last minute changes that came our way and we appreciate that

Reviewed on Apr 18, 2026

Marriott Chicago O'Hare
See all 1,936 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 $1,053. 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

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.