
Illinois Luxury Vacations
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Top Luxury vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥372,712, price is now ¥324,804 per person
¥324,804
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
It's ok, no rats or cockroaches but did I expect better for the price? Yes. And don't be fooled, there are hidden fees, something called a "city resort tax" or something like that (even though it's not a resort--no perks), that you'll be charged additional for at the hotel, no matter what Expedia says about fees and taxes being included in the price.
Reviewed on May 4, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥520,745, price is now ¥431,470 per person
¥431,470
per person
Jul 18 - Jul 23
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.
Reviewed on Apr 22, 2026

The Royal Sonesta Chicago River North
Downtown Chicago
Price was ¥382,886, price is now ¥330,889 per person
¥330,889
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,550 reviews)
Staff was amazing. Thank you for a great visit
Reviewed on May 5, 2026

The Godfrey Hotel Chicago
Downtown Chicago
Price was ¥416,648, price is now ¥363,236 per person
¥363,236
per person
Jul 16 - Jul 20
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,197 reviews)
Location is great for local bars and restaurants. Roof top bar is fabulous view of city at night. Great breakfast cooked to order. Valet parking was super quick on leaving.
Reviewed on May 4, 2026

Omni Chicago Hotel
Downtown Chicago
Price was ¥439,816, price is now ¥390,828 per person
¥390,828
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,773 reviews)
Breakfast at the Omni was the best food I had in Chicago, despite going to other upscale restaurants for lunch and dinner.
Reviewed on Apr 27, 2026
5* Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥409,626, price is now ¥368,570 per person
¥368,570
per person
Jun 4 - Jun 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything
Reviewed on May 4, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥521,059, price is now ¥462,490 per person
¥462,490
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
The staff was very welcoming and the rooms were super clean & well maintained.
The location is also very convenient, quiet but close and walking distance to the river and the amazing restaurants. Will definitely revisit the Penninsula soon.
Reviewed on May 2, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥646,278, price is now ¥606,796 per person
¥606,796
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
3 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥372,712, price is now ¥324,804 per person
¥324,804
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
It's ok, no rats or cockroaches but did I expect better for the price? Yes. And don't be fooled, there are hidden fees, something called a "city resort tax" or something like that (even though it's not a resort--no perks), that you'll be charged additional for at the hotel, no matter what Expedia says about fees and taxes being included in the price.
Reviewed on May 4, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥506,862, price is now ¥430,899 per person
¥430,899
per person
Jun 4 - Jun 7
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything
Reviewed on May 4, 2026

The Royal Sonesta Chicago River North
Downtown Chicago
Price was ¥382,886, price is now ¥330,889 per person
¥330,889
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,550 reviews)
Staff was amazing. Thank you for a great visit
Reviewed on May 5, 2026
4 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥461,280, price is now ¥397,728 per person
¥397,728
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.
Reviewed on Apr 22, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥546,058, price is now ¥442,256 per person
¥442,256
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Very clean room, kind and courteous staff. Would definitely stay again!
Reviewed on May 3, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥546,224, price is now ¥447,068 per person
¥447,068
per person
Jul 19 - Jul 23
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything
Reviewed on May 4, 2026
Top Luxury Illinois Hotels

Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
The price is ¥70,159 per night from May 25 to May 26
¥70,159
¥83,416 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 ...
9.4/10 Exceptional! (1,862 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 ¥71,810 per night from May 25 to May 26
¥71,810
¥85,380 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! (1,007 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 ¥98,131 per night from May 24 to May 25
¥98,131
¥116,673 total
May 24 - May 25
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.
More Vacation Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
