Illinois Romantic Vacations
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Top Romantic vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥85,802, price is now ￥75,411 per person
￥75,411
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
The room was big, enough to fit 4 luggages. Location is fantastic, walkable to a lot of food and shopping places. The best thing was, there was a kettle in the room😂 I like to make my own tea and coffee etc The two previous hotels we stayed at during the same holiday did not have one. Price was affordable too, at time of stay. Will definitely recommend this hotel.
Reviewed on Oct 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.
Reviewed on Oct 26, 2025
Omni Chicago Hotel
Downtown Chicago
Price was ￥108,664, price is now ￥93,543 per person
￥93,543
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
9.2/10 Wonderful! (1,583 reviews)
We wish they had bidet for the toilet.
Noise from all-day long sirens on the roads , very annoying.
Reviewed on Oct 27, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥89,823, price is now ￥79,054 per person
￥79,054
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
5* Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.
Reviewed on Oct 26, 2025
3 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥237,656, price is now ￥220,140 per person
￥220,140
per person
Dec 8 - Dec 11
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
The room was big, enough to fit 4 luggages. Location is fantastic, walkable to a lot of food and shopping places. The best thing was, there was a kettle in the room😂 I like to make my own tea and coffee etc The two previous hotels we stayed at during the same holiday did not have one. Price was affordable too, at time of stay. Will definitely recommend this hotel.
Reviewed on Oct 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥335,652, price is now ￥281,290 per person
￥281,290
per person
Dec 8 - Dec 11
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.
Reviewed on Oct 26, 2025
4 Night Romantic vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥268,162, price is now ￥231,356 per person
￥231,356
per person
Dec 7 - Dec 11
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.
Reviewed on Oct 26, 2025
Top Romantic Illinois Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is ￥13,558 per night from Nov 11 to Nov 12
￥13,558
￥18,173 total
Nov 11 - Nov 12
includes taxes & fees
For a romantic stay, consider this boutique hotel, featuring a garden, jetted tubs, and in-room fireplaces. Couples will appreciate the romance packages and ...
8.4/10 Very Good! (1,306 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Clean, comfortable, Hot water!
Reviewed on Oct 26, 2025
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
The price is ￥23,929 per night from Nov 27 to Nov 28
￥23,929
￥28,090 total
Nov 27 - Nov 28
includes taxes & fees
Indulge in a romantic getaway at this upscale hotel, where you'll find a spa, in-room massages, and onsite dining. Couples will love the Frette Italian sheets ...
9.4/10 Exceptional! (3,370 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
Everything about this Hotel was top tier and prestigious. Highly recommended. Rooms were extremely clean, Staff super friendly and the Breakfast was delicious. You have to try the pancakes and French toast
Reviewed on Oct 27, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
The price is ￥16,099 per night from Nov 24 to Nov 25
￥16,099
￥22,716 total
Nov 24 - Nov 25
includes taxes & fees
You and your special someone are sure to love the
8.4/10 Very Good! (2,043 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
Everything was very good. Just as my previous stays have been
Reviewed on Oct 26, 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.
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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.
