Great Lakes Luxury Vacations 2026

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Top Luxury vacation packages in Great Lakes

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

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

￥148,163

per person

Nov 3 - Nov 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.8/10 Excellent! (2,334 reviews)

Music in restaurant was very annoying. Upon arrival to room on the surface it looked clean but under better inspection much dust was very evident on phone & nightstand, & above the air vent where you can adjust temperature & fan there was dark dirt & what looked like black mold. Molding around floor in bathroom looked like it hadn’t been cleaned in months.

Reviewed on Sep 15, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

￥231,626

per person

Nov 3 - Nov 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

L7 Chicago by LOTTE

Downtown Chicago

Save 100% on your flight

￥169,926

per person

Nov 3 - Nov 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.6/10 Exceptional! (4,700 reviews)

The Langham, Chicago

Downtown Chicago

￥394,280

per person

Nov 18 - Nov 22

found 24 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

￥335,127

per person

Nov 18 - Nov 22

just found

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.2/10 Wonderful! (3,269 reviews)

Comfortable and aesthetic! Enjoyed our stay a lot.

Reviewed on Sep 16, 2026

Don't see what you're looking for?

See all available trips from Dallas to Great Lakes

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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

￥231,626

per person

Nov 3 - Nov 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

The Langham, Chicago

Downtown Chicago

￥394,280

per person

Nov 18 - Nov 22

found 24 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

The Ritz-Carlton, Chicago

Downtown Chicago

￥350,829

per person

Nov 18 - Nov 22

found 24 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.2/10 Wonderful! (1,001 reviews)

Don't see what you're looking for?

See all available trips from Dallas to Great Lakes

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3 Night Luxury vacations in Great Lakes

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

Fairmont Royal York

Downtown Toronto

￥132,314

per person

Nov 17 - Nov 20

found 24 hours ago

Roundtrip flight included

Vancouver (YVR) to Toronto (YYZ)

9/10 Wonderful! (8,632 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

￥437,778

per person

Nov 29 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Fukuoka (FUK) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

Hotel 55 Chicago Downtown

Downtown Chicago

￥373,679

per person

Nov 29 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Fukuoka (FUK) to Chicago (ORD)

8.8/10 Excellent! (1,567 reviews)

Room was clean and comfortable.

Reviewed on Sep 14, 2026

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See all available trips from Vancouver to Great Lakes

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4 Night Luxury vacations in Great Lakes

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

Trump International Hotel & Tower Chicago

Downtown Chicago

￥317,645

per person

Nov 18 - Nov 22

found 24 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

The Langham, Chicago

Downtown Chicago

￥394,280

per person

Nov 18 - Nov 22

found 24 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

￥335,127

per person

Nov 18 - Nov 22

just found

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.2/10 Wonderful! (3,269 reviews)

Comfortable and aesthetic! Enjoyed our stay a lot.

Reviewed on Sep 16, 2026

Don't see what you're looking for?

See all available trips from Tokyo to Great Lakes

View all trips

Top Luxury Great Lakes Hotels

The Omni King Edward Hotel

37 King St E Toronto ON

4 hours drive from Lake Ontario

Discover luxurious lodging at The Omni King Edward Hotel, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe amenities ...

Fairmont Royal York

100 Front St West Toronto ON

4 hours drive from Lake Ontario

Treat yourself to a luxury stay at Fairmont Royal York, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The 4 bars, indoor ...

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 ...

See all 83,831 properties in Great Lakes

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.