Old Town Chicago Vacation Packages
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Top Holiday Package Deals in Old Town Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $3,038, price is now CA $1,492 per person
CA $1,492
per person
May 10 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great staff, clean rooms. Great location
Reviewed on Feb 21, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,614, price is now CA $1,494 per person
CA $1,494
per person
May 10 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
The Wade
Downtown Chicago
Price was CA $2,269, price is now CA $1,486 per person
CA $1,486
per person
May 10 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
We had a really good stay. The hotel is in a great location. We got a lakeview room, and it was right in front of the lake by Navy Pier. The view was beautiful. We had a king-size bed, and it was very comfortable. Check-in and check-out were very quick and easy. That made everything smooth from start to finish. The bathroom was clean and nice. The food and drinks were also very good. The only downside was that our room was close to the elevator, so it was a little noisy. You could hear it going up and down. There were also people smoking weed, and the smell would come in sometimes, which we did not like. But overall, it was a good stay. It was very close to Navy Pier, which was perfect since most of our plans were there.
Reviewed on Feb 22, 2026
Stay One Chicago
Downtown Chicago
Price was CA $4,059, price is now CA $2,768 per person
CA $2,768
per person
May 10 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 2026
Where to stay in Old Town Chicago
Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Old Town Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Feb 23 to Feb 24
CA $122
CA $143 total
Feb 23 - Feb 24
includes taxes & fees
8/10 Very Good! (9,912 reviews)
Everything was clean and neat.
Reviewed on Feb 19, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Mar 4 to Mar 5
CA $136
CA $198 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,387 reviews)
So clean, amazing breakfast - high quality rooms
Reviewed on Feb 22, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Mar 4 to Mar 5
CA $135
CA $158 total
Mar 4 - Mar 5
includes taxes & fees
8.4/10 Very Good! (5,683 reviews)
Nice location, clean room, Happy Hour passes, and included breakfast.
Reviewed on Feb 22, 2026
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.
Frequently asked questions
Things to do
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.