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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,142, price is now CA $755 per person
CA $755
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,780, price is now CA $1,054 per person
CA $1,054
per person
Jul 17 - Jul 21
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,882 reviews)
The HVAC was annoying AF. It would go on and blow cold air for 10 minutes, then be off for 15-20 minutes repeatedly. It is so loud, it kept waking me up through out the night. As a short person, I did not like the fact the bed was a challenge to get on top. Not everyone is five feet tall.

Reviewed on Apr 26, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,447, price is now CA $941 per person
CA $941
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,140, price is now CA $1,398 per person
CA $1,398
per person
Jul 9 - Jul 12
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.

Reviewed on Apr 25, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,416, price is now CA $928 per person
CA $928
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on Apr 25, 2026

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Riverside Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,646 reviews)
Great location nice hotel!

Reviewed on Apr 28, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $197 per night from May 25 to May 26
CA $197
CA $234 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,144 reviews)
Everything was great until morning then our room filled up with smoke otherwise it was good

Reviewed on Apr 27, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from May 25 to May 26
CA $150
CA $178 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,475 reviews)
Parking was more than it should be for overnight at a garage blocks away not tied to the hotel

Reviewed on Apr 29, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 5,169 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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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

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.