Robert W Roloson Houses Tours and Activities
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The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,610, price is now CA $912 per person
CA $912
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.
Reviewed on Apr 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,834, price is now CA $1,197 per person
CA $1,197
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.
Reviewed on Apr 11, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,376, price is now CA $968 per person
CA $968
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 2026
Tours & day trips
See all 197 activities
Architecture River Tour
Activity duration is 1 hour
9.6 out of 10 with 1508 reviews
Free cancellation available
Private & custom tours
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Chicago: Creative Team Building - Paint Your Own Fluid Bear
10.0 out of 10 with 1 review
Free cancellation available
![City centre Chicago City Tour In a Lamborghini[60 Minute Experience]](https://mediaim.expedia.com/localexpert/50806683/b6324a0b-7fb0-4936-8b5f-2fdebe79ae59.jpg?impolicy=resizecrop&rw=500&rh=280)
Food, drink & nightlife
See all 28 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Activity duration is 2 hours and 30 minutes
8.0 out of 10 with 41 reviews
Attractions
See all 19 activities
360 CHICAGO Observation Deck
Activity duration is 2 hours
8.8 out of 10 with 703 reviews
Free cancellation available
Adventure & outdoor
See all 14 activities
Chicago: Two Flight Indoor Skydiving Experience
Activity duration is 1 hour
10.0 out of 10 with 1 review
Free cancellation available
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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.