
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 ¥209,548, price is now ¥152,323 per person
¥152,323
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I love everything in the hotel everything
Reviewed on May 4, 2026

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ¥338,608, price is now ¥305,742 per person
¥305,742
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,054 reviews)
The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!
Reviewed on May 1, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥335,242, price is now ¥304,352 per person
¥304,352
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥348,109, price is now ¥324,906 per person
¥324,906
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
This hotel gives that WOW factor. The hotel was built in the1920 and the details are breath taking. What an incredible experience spend that extra coin to get the river view. It was totally worth it. We had room service for breakfast just a classic breakfast and it was delicious.the robes /slippers were such a lush touch. Rooftop patio is amazing. It will get busy. I just wish that it was available to guests first. Cute vibe. The staff are amazing and so sweet! Everything we wanted to do was 15 minutes tops. Great location! We loved walking around the town! Take the architectural tour. All of the buildings are truly masterpieces. Thanks for such a wonderful experience we loved it so much!
Reviewed on May 7, 2026
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 ¥209,548, price is now ¥152,323 per person
¥152,323
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Albany (ALB) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I love everything in the hotel everything
Reviewed on May 4, 2026

The Ritz-Carlton, Chicago
Downtown Chicago
Price was ¥390,562, price is now ¥390,562 per person
¥390,562
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
We’ve stayed at some really nice hotels so keeping that in mind, we had high expectations for this being our first Ritz Carlton stay and it just fell really flat. The front desk staff were nice enough but nothing overly warm or anything that separated it from any other hotel. The room was clean but again pretty average. The bed was very comfortable but the pillows which are down or down alternative had such a low fill power, they were just awful. The most disappointing part of the stay was by far the room service. Our bill totaled nearly $300 which we’re happy to spend if it’s good but the chicken wings which are advertised as “crispy” couldn’t have been further from —extremely rubbery. My husband described his waygu steak “like eating a car tire” (never experienced waygu that bad before.) The cocktail sauce for the shrimp cocktail had zero horseradish. Just a very odd experience overall and it was enough to not order room service again for the remainder of our stay. The spa was also very …average. My husband said his massage was actually pretty good but mine was nothing at all out of the ordinary… probably one of the lowest ranking I’ve received honestly. The staff at the spa desk and in the locker room though were probably the best part of our whole experience — very friendly, helpful and accommodating. All in all, it wasn’t a terrible stay here but it wasn’t great either. Location is solid but I’d save some money and stay elsewhere to get better food and pillows.
Reviewed on Apr 21, 2026
Top Luxury Illinois Hotels

Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
The price is ¥69,758 per night from May 25 to May 26
¥69,758
¥82,934 total
May 25 - May 26
includes taxes & 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 ...
9.6/10 Exceptional! (1,864 reviews)
I love everything in the hotel everything
Reviewed on May 4, 2026

The Langham, Chicago
330 North Wabash Avenue Chicago IL
The price is ¥82,068 per night from May 25 to May 26
¥82,068
¥97,573 total
May 25 - May 26
includes taxes & 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 ...
9.8/10 Exceptional! (1,012 reviews)
This was THE BEST hotel we had ever stayed in.
Reviewed on May 4, 2026

The Peninsula Chicago
108 East Superior Street Chicago IL
The price is ¥97,700 per night from May 25 to May 26
¥97,700
¥116,154 total
May 25 - May 26
includes taxes & fees
Treat yourself to some luxurious accommodations at The Peninsula Chicago, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe ...
9.8/10 Exceptional! (1,006 reviews)
the staff is the absolute nicest and eficient in Chicago. Location is prime, Spa is top notch. Rooms are all extremely quiet. Shaghai Terrace has the best Peking Duck in the world, wonderful presentation, You will not regret the stay.
Reviewed on May 3, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
