Riverside Vacations from $385
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Riverside vacation packages
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
$385
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop
Reviewed on Oct 19, 2026
Swissotel - Chicago
Downtown Chicago
$542
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
I traveled from Cincinnati Ohio and the room on the 36th floor had a great view of Lake Michigan. Valet staff for parking was excellent as well. Highly recommended if you’re planning to visit Chicago.
Reviewed on Oct 19, 2026
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.
What to do in Riverside
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
Riverside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$108 nightly
$129 total
Nov 11 - Nov 12
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Nov 1 - Nov 2
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$121 nightly
$143 total
Nov 11 - Nov 12
Total with taxes and fees
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.
Find the Best Riverside Vacation Packages
Riverside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 8,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Chicago Riverwalk, John G. Shedd Aquarium and Art Institute of Chicago |
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Frequently asked questions
How much does a Riverside vacation package cost?
You can snap up a vacation package to this top destination from $385 on Expedia. But 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?
December, January and February are the best times to search for cheap Riverside vacation packages. Opting to travel in quieter periods means you'll typically find better prices on accommodations and flights.
How many days is enough for Riverside?
The ideal duration for your Riverside vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to check out all the leading sights and explore some hidden spots along the way.
How to find the best Riverside package deals?
Finding a cheap Riverside package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Riverside package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away 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 great savings when compared to arranging flights and stays individually. Better still, you can customize your Riverside getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Riverside?
If you've got your Riverside travel dates locked in, book as early as you can to bag some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Riverside?
- Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to go to Riverside.
- Set a budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to Riverside. Then, choose a property that works with your budget, whether that's a low-cost stay or a deluxe retreat.
- Organize your Riverside getaway with Expedia's trip planning tool: Search for and book stays and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Riverside together.
- Decide how many days away: Start by making a list of all the attractions you'd like to experience in Riverside. Then, estimate how long you'll need at each, including any travel time.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Riverside vacation package that brings all your bookings together.
- Add on excursions and experiences: Read our travel guide to find some exciting things to do in Riverside. Book tickets or make reservations as soon as you can to save time and skip the hassle of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Riverside vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Riverside trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.