Great Lakes Luxury Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Luxury vacation packages in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ₩1,261,054, price is now ₩884,314 per person
₩884,314
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay.
Reviewed on Jul 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,254,361, price is now ₩1,617,928 per person
₩1,617,928
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service
Reviewed on Jun 30, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,268,322, price is now ₩1,696,016 per person
₩1,696,016
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ₩1,202,052, price is now ₩919,256 per person
₩919,256
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,222 reviews)
Clean Room, great staff and good location.
Reviewed on Jul 2, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ₩1,221,395, price is now ₩943,132 per person
₩943,132
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,392 reviews)
Gorgeous property, excellent view and room was very clean. Staff were friendly and helpful.
Reviewed on Jun 21, 2026
5* Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,254,361, price is now ₩1,617,928 per person
₩1,617,928
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service
Reviewed on Jun 30, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,268,322, price is now ₩1,696,016 per person
₩1,696,016
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
3 Night Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ₩1,261,054, price is now ₩884,314 per person
₩884,314
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay.
Reviewed on Jul 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,254,361, price is now ₩1,617,928 per person
₩1,617,928
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service
Reviewed on Jun 30, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,268,322, price is now ₩1,696,016 per person
₩1,696,016
per person
Sep 2 - Sep 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
Top Luxury Great Lakes Hotels
The Omni King Edward Hotel
37 King St E Toronto ON
Discover luxurious lodging at The Omni King Edward Hotel, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe amenities ...
9.6/10 Exceptional! (2,646 reviews)
"My FAVORITE hotel that I’ve stayed at in the past 6 months! Very clean, the food service is great and the staff was lovely! If you’re ever in downtown Toronto, this is the place to stay!"
Reviewed on Jul 2, 2026
Fairmont Royal York
100 Front St West Toronto ON
Treat yourself to a luxury stay at Fairmont Royal York, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The 3 bars, indoor ...
9/10 Wonderful! (8,293 reviews)
"We had a wonderful stay at the Fairmont Royal York! We did have a couple issues upon check-in however the manager immediately handled the situation. The rooms were very comfortable, the staff was very friendly and attentive. The housekeeper even knew my name and would greet me every time she saw ..."
Reviewed on Jul 3, 2026
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Trump International Hotel & Tower Chicago is a lush 5-star boutique property where you can be treated to deep soaking bathtubs and pillowtop beds. The spa, indoor ...
9.6/10 Exceptional! (1,912 reviews)
"Great service"
Reviewed on Jun 30, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
