Riverside Vacations from $442

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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.

The Latest Riverside vacation packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $442 per person
$442
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,360 reviews)
Location is closer to Navy pier. Not a lot of nice food options around.

Reviewed on Jun 3, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $806, price is now $514 per person
$514
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
It is a great place to stay. The breakfast was good. However, you don’t get toothpaste and some other bathroom amenities which is something they can improve.

Reviewed on Jun 4, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,252, price is now $819 per person
$819
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 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
Save 100% on your flight
Price was $961, price is now $633 per person
$633
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.

Reviewed on Jun 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,645, price is now $1,093 per person
$1,093
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic

Reviewed on Jun 3, 2026

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Discover the most popular places to visit in Riverside

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

What to do in Riverside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$174
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
See all activities in Riverside

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
$145 nightly
The price is $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,169 reviews)
"Well located yet aged facility. Bathrooms are small and frankly nasty. It served our purpose as a base for a 3-day stay in Chicago with errands to run in the nearby area."

Reviewed on Jun 4, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
$154 nightly
The price is $183 total per night from Jun 28 to Jun 29
$183 total
Jun 28 - Jun 29
Total with taxes and fees
7.8/10 Good! (1,518 reviews)
"Clean room"

Reviewed on Jun 3, 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $242 total per night from Jun 30 to Jul 1
$242 total
Jun 30 - Jul 1
Total with taxes and fees
9.4/10 Exceptional! (4,336 reviews)
"Nice staff. Clean. Great rooftop bar!! Great location. Great included breakfast buffet! I prefer a comforter rather than a sheet and blanket but still loved it!!"

Reviewed on Jun 5, 2026

Hotel Riu Plaza Chicago
See all 5,092 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.

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 $442 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.