Rush Street Luxury Vacations 2026

Top Luxury vacation packages in Rush Street

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

Thompson Chicago, by Hyatt

Downtown Chicago

$446

per person

Nov 1 - Nov 3

found 20 hours ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

9.2/10 Wonderful! (1,421 reviews)

Best Location. Best Service. Best Patio!

Reviewed on Oct 2, 2026

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

$847

per person

Dec 4 - Dec 6

found 6 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,003 reviews)

It was such a joy to stay at the Park Hyatt for our wedding! The staff at the Hyatt went above and beyond to make our stay memorable. It was all fabulous from the staff, to the food, to the beautiful views.

Reviewed on Oct 1, 2026

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5* Luxury vacations in Rush Street

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

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

$847

per person

Dec 4 - Dec 6

found 6 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,003 reviews)

Reviewed on Oct 1, 2026

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See all available trips from Columbus to Rush Street

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3 Night Luxury vacations in Rush Street

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

Thompson Chicago, by Hyatt

Downtown Chicago

Save 100% on your flight

$596

per person

Dec 2 - Dec 5

found 13 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.2/10 Wonderful! (1,421 reviews)

Best Location. Best Service. Best Patio!

Reviewed on Oct 2, 2026

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

$1,041

per person

Dec 4 - Dec 7

found 23 hours ago

Roundtrip flight included

Baltimore (BWI) to Chicago (ORD)

9.6/10 Exceptional! (1,003 reviews)

Reviewed on Oct 1, 2026

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4 Night Luxury vacations in Rush Street

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

Thompson Chicago, by Hyatt

Downtown Chicago

$1,057

per person

Dec 2 - Dec 6

found 6 hours ago

Roundtrip non-stop flight included

Corpus Christi (CRP) to Chicago (ORD)

9.2/10 Wonderful! (1,421 reviews)

Best Location. Best Service. Best Patio!

Reviewed on Oct 2, 2026

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

$1,380

per person

Dec 10 - Dec 14

found 11 hours ago

Roundtrip flight included

Minneapolis (MSP) to Chicago (ORD)

9.6/10 Exceptional! (1,003 reviews)

Reviewed on Oct 1, 2026

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What can I expect from a luxury Rush Street vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Rush Street 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 Rush Street?

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 Rush Street 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 $446. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Rush Street?

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 Rush Street 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 Rush Street?

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 Rush Street 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 Rush Street 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.