Chicago Ridge Vacation Packages

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Your Chicago Ridge Vacation

Say bye-bye to the hassle of planning and hello to a Chicago Ridge vacation package. With everything organized before you take off, you can focus on discovering the best of this city, starting with Hyde Park, which is great for history, nature and culture. If your trip to Chicago Ridge includes a little sightseeing, drop by renowned attractions like SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College. Your perfect Chicago Ridge vacation is only clicks away. Explore accommodations, flights and more on Expedia for an adventure that's tailored just for you.

Top Chicago Ridge Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,156, price is now CA $768 per person
CA $768
per person
Jun 11 - Jun 15
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (484 reviews)
small town main street neighborhood, good food nearby, shopping

Reviewed on May 1, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,953, price is now CA $1,143 per person
CA $1,143
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Breakfasr good, view great

Reviewed on May 1, 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 $2,030, price is now CA $1,293 per person
CA $1,293
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
I loved it. The location was perfect and I specifically pick this hotel based on the view and it did not disappoint. If you don’t wanna go far, there are plenty of restaurants and things to do right around the hotel so that was also convenient. I will definitely be going back.

Reviewed on May 1, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back

Reviewed on Apr 27, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,778, price is now CA $1,866 per person
CA $1,866
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Best Hotel in Chicago

Reviewed on Apr 27, 2026

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Chicago Ridge 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! (2,659 reviews)
I recently stayed at Hotel Felix and overall had a decent experience. The location is great and very convenient, and the staff were friendly and welcoming throughout my stay. The room itself was clean and comfortable. The only issue I experienced was mold on the bathroom wall and ceiling. I contacted ...

Reviewed on May 2, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,150 reviews)
EXCELLENT LOCATION

Reviewed on May 2, 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
The price is CA $183 per night from May 27 to May 28
CA $183
CA $256 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,029 reviews)
The lack of service at breakfast

Reviewed on May 2, 2026

Hotel Riu Plaza Chicago
See all 4,493 properties in Chicago Ridge
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
Family Vacations
Family Vacations

Discover the most popular places to visit in Chicago Ridge

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 Chicago Ridge

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 Chicago Ridge

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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.