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 Holidays

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Top Luxury holiday packages in Great Lakes

Price found within the past 48 hours. Click for updated prices.
  • 8 Oct - 14 Oct

    Ivy Boutique Hotel + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.8/10 - Excellent (1,369 reviews)
    Return Hong Kong SAR (HKG) - Chicago (ORD)
    HKG - ORD1 stop ORD - HKG1 stop
    HK$18,026
    HK$15,240
    per traveller
    found 14 hours ago
    Ivy Boutique Hotel
  • 8 Oct - 14 Oct

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,948 reviews)
    "Super Clean room"
    Reviewed July 23, 2026
    Return Hong Kong SAR (HKG) - Chicago (ORD)
    HKG - ORD1 stop ORD - HKG1 stop
    Save 100% on your flight
    HK$43,539
    HK$31,828
    per traveller
    found 14 hours ago
    Trump International Hotel & Tower Chicago
  • 8 Oct - 14 Oct

    The Godfrey Hotel Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.8/10 - Excellent (2,346 reviews)
    "Very little water pressure and no response when we asked for a solution. Drinks on the rooftop were overpriced and horrible"
    Reviewed July 24, 2026
    Return Hong Kong SAR (HKG) - Chicago (ORD)
    HKG - ORD1 stop ORD - HKG1 stop
    HK$21,716
    HK$15,882
    per traveller
    found 14 hours ago
    The Godfrey Hotel Chicago
  • 8 Oct - 14 Oct

    L7 Chicago by LOTTE + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.6/10 - Exceptional (4,431 reviews)
    Return Hong Kong SAR (HKG) - Chicago (ORD)
    HKG - ORD1 stop ORD - HKG1 stop
    HK$23,361
    HK$17,848
    per traveller
    found 14 hours ago
    L7 Chicago by LOTTE
  • 8 Oct - 14 Oct

    The Royal Sonesta Chicago River North + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (2,736 reviews)
    Return Hong Kong SAR (HKG) - Chicago (ORD)
    HKG - ORD1 stop ORD - HKG1 stop
    HK$19,298
    HK$16,516
    per traveller
    found 14 hours ago
    The Royal Sonesta Chicago River North

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 holidays in Great Lakes

What can I expect from a luxury Great Lakes holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

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

Tick the all-inclusive and 5-star filters to find the crème de la crème of Great Lakes holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Great Lakes?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Great Lakes starting at HK$15,240. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Great Lakes?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Great Lakes spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Great Lakes?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Great Lakes?

You can wangle a top-notch luxury holiday in Great Lakes for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

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

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

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

Nobody does luxury quite like Expedia. With so many gorgeous properties in Great Lakes to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.