A modern bridge with a reflection in the water, surrounded by historic buildings and tall skyscrapers.
Photo by Leo Li
Open Photo by Leo Li

Great Lakes Luxury Vacations

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Top Luxury vacation packages in Great Lakes

Price found within the past 48 hours. Click for updated prices.
  • Aug 24 - Aug 28

    Canopy By Hilton Toronto Yorkville + Flight

    Downtown Toronto
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,418 reviews)
    Roundtrip Tokyo (TYO) - Toronto (YYZ)
    NRT - YYZNonstop YYZ - HNDNonstop
    ¥357,810
    ¥322,917
    per traveler
    found 15 hours ago
    Canopy By Hilton Toronto Yorkville
  • Oct 6 - Oct 9

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,145 reviews)
    "The first room we were assigned smelled like a cat. I'm severely allergic, so I knew right away (room 2204). The second room (1404) was nice and clean. Unfortunately the noise from Michigan Avenue is pretty much unbearable. It's an old building and no sound proofing has been done to the walls ... even from the 14th floor I could hear sirens all night, cars drag racing, and even gun shots. There are 5-6 elevators on this property, but the first set of 3 services the lobby to floor 22, and..."
    Reviewed July 23, 2026
    Roundtrip Tokyo (TYO) - Chicago (ORD)
    HND - ORD1 stop ORD - HND1 stop
    ¥483,044
    ¥404,096
    per traveler
    found 0 hours ago
    Pendry Chicago
  • Oct 6 - Oct 9

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    2 nights
    5.0 star property
    9.6/10 - Exceptional (1,948 reviews)
    "Super Clean room"
    Reviewed July 23, 2026
    Roundtrip Tokyo (TYO) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥401,228
    ¥343,776
    per traveler
    found 4 hours ago
    Trump International Hotel & Tower Chicago
  • Sep 30 - Oct 2

    Shangri-La Toronto + Flight

    Downtown Toronto
    2 nights
    5.0 star property
    9.6/10 - Exceptional (1,313 reviews)
    Roundtrip Tokyo (HND) - Toronto (YYZ)
    HND - YYZNonstop YYZ - HNDNonstop
    ¥379,539
    ¥332,132
    per traveler
    found 1 day ago
    Shangri-La Toronto
  • Oct 6 - Oct 9

    L7 Chicago by LOTTE + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.6/10 - Exceptional (4,431 reviews)
    Roundtrip Tokyo (TYO) - Chicago (ORD)
    HND - ORD1 stop ORD - HND1 stop
    ¥432,162
    ¥396,742
    per traveler
    found 0 hours ago
    L7 Chicago by LOTTE

Discover the most popular places to visit in Great Lakes

What to do in Great Lakes

Top Luxury Great Lakes Hotels

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.

All you need to know about luxury vacations in Great Lakes

What can I expect from a luxury Great Lakes vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Great Lakes vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Great Lakes?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Great Lakes luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at ¥322,917. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Great Lakes?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Great Lakes with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Great Lakes?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Great Lakes with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Great Lakes with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.