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



Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,561, price is now €1,747 per person
€1,747
per person
10 Oct - 14 Oct
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €1,284, price is now €880 per person
€880
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on 21 Aug 2025

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

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,561, price is now €1,747 per person
€1,747
per person
10 Oct - 14 Oct
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025

The Peninsula Chicago
Downtown Chicago
Price was €2,551, price is now €1,840 per person
€1,840
per person
10 Oct - 14 Oct
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
This is a truly luxurious hotel. I highly recommend it. You can not find a better hotel in Chicago
Reviewed on 20 Aug 2025
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,561, price is now €1,747 per person
€1,747
per person
10 Oct - 14 Oct
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025


The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is €100 per night from 25 Aug to 26 Aug
€100
25 Aug - 26 Aug
includes taxes & fees
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,205 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
"Everything was fine."
Reviewed on 21 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
The price is €195 per night from 1 Sept to 2 Sept
€195
1 Sept - 2 Sept
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.4/10 Exceptional! (3,333 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
"Bartender Jax (Joaquin) was AMAZING!!!"
Reviewed on 23 Aug 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
The price is €195 per night from 2 Sept to 3 Sept
€195
2 Sept - 3 Sept
includes taxes & fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,882 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
"A+"
Reviewed on 21 Aug 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.