Riverside Vacation Packages

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

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Your Riverside Vacation

The easiest way to experience this vibrant city is with a custom-made Riverside vacation package. Stay in the neighborhood of Magnificent Mile, which is good for cafes, shopping and history or choose someplace else — our packages are all about you. Any trip to Riverside needs a well-designed itinerary. Fill yours with major attractions such as Brookfield Zoo, SeatGeek Stadium and Frank Lloyd Wright Historic District. Expedia has what you need to escape the everyday. Tailor your vacation to Riverside to suit your travel style, whatever that may be.

Top Riverside 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 $1,259, price is now CA $941 per person
CA $941
per person
Jan 17 - Jan 21
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,559, price is now CA $1,037 per person
CA $1,037
per person
Dec 19 - Dec 23
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was CA $2,031, price is now CA $1,315 per person
CA $1,315
per person
Dec 24 - Dec 31
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)
Make sure what you order is what you get .... I had to extend my neck to see the river that I paid for. Room was spacious .... but the gentleman checking me in could have been a little more friendlier with my concerns.

Reviewed on Nov 1, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,339, price is now CA $1,641 per person
CA $1,641
per person
Jan 17 - Jan 21
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,300, price is now CA $993 per person
CA $993
per person
Jan 9 - Jan 14
found 24 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Ready to book your vacation to Riverside?

 

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Riverside Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (10,085 reviews)
"it needs a lot of work. our bathroom had several cracks in the floor. , a huge gaping hole in the ceiling , dried dirt and hair on bathroom doors, the showered were stained and rusty, i couldn’t even shower in there because of how disgusting it was. the hotel was 14 floor and only one working elevator. ..."

Reviewed on Nov 1, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Dec 2 to Dec 3
CA $173
CA $206 total
Dec 2 - Dec 3
includes taxes & fees
8/10 Very good! (2,636 reviews)
"Great location and staff were kind! Would stay here again"

Reviewed on Nov 1, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $198 total
Nov 23 - Nov 24
includes taxes & fees
8.8/10 Excellent! (5,584 reviews)
"Amazing staff and view! Highly recommend"

Reviewed on Nov 1, 2026

River Hotel
See all 5,093 properties in Riverside
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
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Beach Vacations
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Stay near popular Riverside attractions

Riverside Arts Center

Enjoy an outing to Riverside Arts Center during your stay in Riverside. Amble around the area's riverfront or visit its shops.
See properties

What to do in Riverside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Riverside

Frequently asked questions

How much does a Riverside vacation package cost?
You can snap up a vacation package to this popular destination from CA $941 on Expedia. However, how much your vacation to Riverside costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Riverside?
The off-season is the best time to visit Riverside if you're hoping to keep costs down. Another tip for scoring cheap Riverside vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Riverside?
Allow at least 2 days for your Riverside vacation if you're hoping to enjoy everything that makes this place special. Stroll around key areas, including Archer Heights and Clearing. Then head to the top sights like Unity Temple and Galloping Ghost. With a well-organized itinerary, you can keep busy with room for some rest time too. Want to venture outside of Riverside? Consider fitting in an excursion or two.
How to find the best Riverside package deals?
Bagging a cheap Riverside package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Riverside package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Riverside vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can tailor your Riverside escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Riverside?
Land fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Riverside vacation.
How to plan a trip to Riverside?

  1. Choose when to travel: Check your calendar and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to vacation in Riverside.
  2. Plan your budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Riverside.
  3. Work out your trip length: Consider how long you'd like to spend discovering Riverside. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Riverside vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.