Name: Caesars Windsor - A Caesars Rewards Destination
Price range: $84 total
Rating: 8.6

Your Southwestern Ontario Vacation

When wanderlust beckons, answer it with a vacation package to Southwestern Ontario. Get set to enjoy nature, culture, history, and more in this exciting destination. A trip to Southwestern Ontario wouldn't be complete without getting to some of its leading cities, starting with Hamilton. Some of the top attractions here include Tim Hortons Field and Village Theatre Waterdown. Windsor is another favorite with Southwestern Ontario travelers. Visitors to this exciting city enjoy Detroit Windsor Tunnel and Caesars Casino. Expedia is a one-stop shop when it comes to planning your Southwestern Ontario vacation. From flights and accommodations, to rental cars and activities, we know how to curate a travel experience like no other.

The Latest Southwestern Ontario vacation packages

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

TOOR Hotel Toronto, part of JdV by Hyatt

Downtown Toronto

$730

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Toronto (YYZ)

9.4/10 Exceptional! (785 reviews)

Great place to stay Close to everything Toronto has to offer

Reviewed on Jun 27, 2026

Hotel Riu Plaza Toronto

Downtown Toronto

$1,523

per person

Sep 9 - Sep 16

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Toronto (YYZ)

9.2/10 Wonderful! (3,715 reviews)

Breakfast is a must get in this hotel. . It's really good. You will be satisfied. Staff is great and make you feel comfortable. The hotel doesn't have its own parking but there is a couple of places near where you can park.

Reviewed on Jun 27, 2026

1 Hotel Toronto

Downtown Toronto

$1,300

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Toronto (YYZ)

9.6/10 Exceptional! (748 reviews)

I was concerned when I arrived because I was in the heart of downtown during the World Cup, and this clearly was a bustling location. The clientele all appeared well-heeled and ready for a good time. I personally prefer a low key quiet stay, and I expressed that desire to the staff. They reserved me a beautiful room on a higher floor. I told them that I am partial to quite few pillows and found a veritable pillow fort waiting for me! I had asked for a steamer to prepare a dress for an event I was attending and one was brought to me almost immediately. The staff were incredibly warm and welcoming. The hotel itself if beautiful. Truly the only constructive feedback I could give was that there was no jam with my croissant, and no English Breakfast tea in my room. Both entirely non-issues. I will absolutely be staying here again.

Reviewed on Jun 17, 2026

One King West Hotel & Residence

Downtown Toronto

$886

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Toronto (YYZ)

9.4/10 Exceptional! (7,991 reviews)

I would easily give this hotel five stars, except for one recurring issue. Leaving dirty laundry bins in the hallway next to the elevators 24/7 was an eyesore and felt quite distasteful. Aside from that, everything else was fantastic. The food was great, the service was marvelous, the fellow guests were wonderful, and I truly enjoyed the atmosphere and location.

Reviewed on Jun 26, 2026

Elegant Downtown Apartments

Downtown Toronto

$739

per person

Aug 6 - Aug 10

found 7 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Toronto (YYZ)

8/10 Very Good! (669 reviews)

Communication is a big issue. The listed number did not have voicemail capability. Staff are not local most likely overseas best time to call and get response is between 6 am - 10 am EST. Dryer was not functioning during entire stay. Customer support indicated local support would be contacted. Never heard from anyone. Do not expect to watch anything other than Netflix during stay. Hulu was not available as advertised and local channels not available. Great location, adequately clean. Deposit refunded within 2 days

Reviewed on Jun 24, 2026

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Where to stay in Southwestern Ontario

Find the best Southwestern Ontario areas and neighborhoods for the activities you enjoy most. Learn more about Southwestern Ontario

A park with green grass, trees, benches, and a tall building in the background.

Downtown London

4/5(89 area reviews)

The urban hub of Ontario’s Western University features a variety of British-inspired attractions and the calm beauty of nature.

Stay near popular Southwestern Ontario attractions

A snow-covered ski resort at night with illuminated buildings and ski slopes.

Blue Mountain Ski Resort

9.0/5 (1,956 reviews)

From skiing and snow sports to mountain biking and zip-line tours, there are exciting activities throughout the year at this Ontario mountain resort.

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Southwestern Ontario Hotel Deals

Best Western Plus Lamplighter Inn & Conference Centre

591 Wellington Rd S. London ON

Fully refundableReserve now, pay when you stay

$111 nightly

$132 total

Jul 5 - Jul 6

Total with taxes and fees

8.8/10 Excellent! (1,818 reviews)

"Good place will come again"

Reviewed on Jun 25, 2026

Best Western Plus Waterfront Hotel

277 Riverside Drive West Windsor ON

Fully refundableReserve now, pay when you stay

$78 nightly

$93 total

Jul 1 - Jul 2

Total with taxes and fees

8.2/10 Very Good! (1,033 reviews)

"We arrived little late in the evening and we were almost pass the opening for the kitchen hours The waitress was so nice and asked the manager and they accommodate us with food. Very professional, very nice. We are extremely satisfied staying in the hotel."

Reviewed on Jun 27, 2026

Caesars Windsor - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON

$70 nightly

$84 total

Jul 13 - Jul 14

Total with taxes and fees

8.6/10 Excellent! (3,273 reviews)

"Walking from self parking to the hotel check in was a bit of a walk."

Reviewed on Jun 26, 2026

See all 5,143 properties in Southwestern Ontario

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.