Riverside Vacation Packages

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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.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,351, price is now CA $1,021 per person
CA $1,021
per person
Jul 17 - Jul 20
found 2 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.4/10 Very Good! (1,954 reviews)
Very comfortable bed, spacious room, and great location!

Reviewed on Jun 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,585, price is now CA $1,140 per person
CA $1,140
per person
Aug 20 - Aug 23
found 8 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
Staff was amazing. Great hotel and location!

Reviewed on Jun 8, 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 $1,855, price is now CA $1,370 per person
CA $1,370
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually.

Reviewed on Jun 8, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,815, price is now CA $1,368 per person
CA $1,368
per person
Jul 16 - Jul 19
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable.

Reviewed on Jun 8, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,429, price is now CA $1,080 per person
CA $1,080
per person
Jul 17 - Jul 20
found 2 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
beautiful room city view excellent location quiet and comfortable

Reviewed on Jun 9, 2026

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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 $189 per night from Jun 29 to Jun 30
CA $189
CA $225 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,221 reviews)
"Fantastic room and location."

Reviewed on Jun 9, 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
The price is CA $212 per night from Jun 28 to Jun 29
CA $212
CA $252 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,543 reviews)
"Our room was spacious and very clean"

Reviewed on Jun 8, 2026

The Chicago Hotel Collection - Magnificent Mile
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 $230 per night from Jun 29 to Jun 30
CA $230
CA $273 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,568 reviews)
"We just stayed one night but the hotel served its purpose. We would stay here again. We also liked the lobby of the hotel and bar"

Reviewed on Jun 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 5,088 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.
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Discover the most popular places to visit in Riverside

Wrigley Field

Wrigley Field

4.5/5(159 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(3 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(460 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

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Riverside

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