Chicago Romantic Holidays
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Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was €941, price is now €628 per person
€628
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone was wonderful and the property and rooms are very well maintained. Will definitely stay there again.
Reviewed on 24 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €1,825, price is now €1,216 per person
€1,216
per person
10 Oct - 14 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.
Reviewed on 23 Aug 2025
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
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 12 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 12 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €1,825, price is now €1,216 per person
€1,216
per person
10 Oct - 14 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.
Reviewed on 23 Aug 2025
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 12 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
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
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
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.