Riverside Vacations from $496

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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.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $822, price is now $496 per person
$496
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Breakfast menu was good, staff at the lounge was good. Checking in was not so good, they wanted to charge me $25 to check in 15 minutes before the time. I think it would be better to say the room is not ready yet the saying your room is ready but is not 2 and if you want it now it will be an extra $25. That I think is ridiculous, which took away from my experience.

Reviewed on May 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,475, price is now $769 per person
$769
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Wonderful experience, beautiful place. Breakfast on site was a huge plus!

Reviewed on May 13, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,345, price is now $702 per person
$702
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!

Reviewed on May 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
Save 100% on your flight
Price was $1,622, price is now $1,002 per person
$1,002
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,454, price is now $915 per person
$915
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location. Very friendly and helpful staff.

Reviewed on May 13, 2026

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Discover the most popular places to visit in Riverside

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

4.5/5(461 reviews)

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

4.5/5(4,925 reviews)

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
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$22
per child
98% of travellers recommend
Flyover in Chicago
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
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,227 reviews)
Not the best and not the worst. Tolerable

Reviewed on May 14, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $171 total per night from May 25 to May 26
$171 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (5,166 reviews)
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!

Reviewed on May 11, 2026

River Hotel
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
$150 nightly
The price is $179 total per night from May 25 to May 26
$179 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (4,137 reviews)
Clean great staff. Good location . Would recommend

Reviewed on May 14, 2026

Hotel Riu Plaza Chicago
See all 5,118 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 $496 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.