
West Side Luxury Vacations
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Top Luxury vacation packages in West Side

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Reviewed on Aug 20, 2025


citizenM Chicago Downtown
Reviewed on Aug 22, 2025


Omni Chicago Hotel
Reviewed on Aug 22, 2025
5* Luxury vacations in West Side

Trump International Hotel & Tower Chicago
Reviewed on Aug 19, 2025

Park Hyatt Chicago
Reviewed on Aug 10, 2025

The Langham, Chicago
Reviewed on Aug 12, 2025
3 Night Luxury vacations in West Side

Wind Creek Southland Casino and Hotel
Reviewed on Aug 18, 2025

citizenM Chicago Downtown
Reviewed on Aug 22, 2025

Trump International Hotel & Tower Chicago
Reviewed on Aug 19, 2025
4 Night Luxury vacations in West Side

Fairmont Chicago at Millennium Park
Reviewed on Aug 22, 2025

Hotel Riu Plaza Chicago
Reviewed on Aug 22, 2025

Trump International Hotel & Tower Chicago
Reviewed on Aug 19, 2025
All you need to know about luxury vacations in West Side
What can I expect from a luxury West Side vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury West Side 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 West Side?
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 West Side 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 $299. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in West Side?
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 West Side 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 West Side?
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 West Side 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 West Side 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.