Illinois Luxury Vacations
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Top Luxury vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,159, price is now $722 per person
$722
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Tulsa (TUL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,280, price is now $770 per person
$770
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,698, price is now $1,055 per person
$1,055
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,353, price is now $872 per person
$872
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one.
Reviewed on Sep 15, 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,597, price is now $1,066 per person
$1,066
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Beautiful hotel, great decor, super gym and pool
Reviewed on Oct 14, 2025
5* Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,159, price is now $722 per person
$722
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Tulsa (TUL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,280, price is now $770 per person
$770
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,698, price is now $1,055 per person
$1,055
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
3 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $490, price is now $342 per person
$342
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,994 reviews)
Even though this hotel advertised as a luxury hotel, it is not- the hotel is old and needs to be upgraded. There were cracks everywhere and the bench in the entry was filthy. There was no TV remote in the room, had to ask for one and when it came it did not work well. The food is over priced and is no pool in the hotel.
Reviewed on Oct 23, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,159, price is now $722 per person
$722
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Tulsa (TUL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,559, price is now $1,076 per person
$1,076
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
4 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,280, price is now $770 per person
$770
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,493, price is now $911 per person
$911
per person
Dec 26 - Dec 30
found 9 hours ago
Roundtrip flight included
Orange County (SNA) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,698, price is now $1,055 per person
$1,055
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
All you need to know about luxury vacations in Illinois
What can I expect from a luxury Illinois vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Illinois 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 Illinois?
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 Illinois 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 $342. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in Illinois?
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 Illinois 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 Illinois?
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 Illinois 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 Illinois 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.
Top Luxury Illinois Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
$431 nightly
The price is $506 total per night from Nov 2 to Nov 3
$506 total
Nov 2 - Nov 3
Total with taxes and fees
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 ...
9.4/10 Exceptional! (1,769 reviews)
Stay was great, The service is usually awesome. One night they didn’t even clean the room.
Reviewed on Oct 19, 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
$500 nightly
The price is $587 total per night from Nov 16 to Nov 17
$587 total
Nov 16 - Nov 17
Total with taxes and fees
Enjoy a posh stay at The Langham, Chicago, where you'll find deep soaking bathtubs and a champagne service. Deluxe amenities at this hotel include a spa, an ...
9.6/10 Exceptional! (1,013 reviews)
Great beds
Reviewed on Oct 14, 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
$575 nightly
The price is $675 total per night from Nov 16 to Nov 17
$675 total
Nov 16 - Nov 17
Total with taxes and fees
Treat yourself to some luxurious accommodations at The Peninsula Chicago, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe ...
9.6/10 Exceptional! (1,013 reviews)
Beautiful hotel, great decor, super gym and pool
Reviewed on Oct 14, 2025
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
