Chicago Romantic Holidays
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Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €848, price is now €729 per person
€729
per person
2 Apr - 5 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,208 reviews)
Beautiful facility, great location, nice bed, good shower.
Reviewed on 25 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,665, price is now €1,225 per person
€1,225
per person
14 Mar - 18 Mar
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,358, price is now €1,110 per person
€1,110
per person
3 Mar - 7 Mar
found 8 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026
The Peninsula Chicago
Downtown Chicago
Price was €1,885, price is now €1,559 per person
€1,559
per person
3 Mar - 7 Mar
found 8 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €848, price is now €729 per person
€729
per person
2 Apr - 5 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,208 reviews)
Beautiful facility, great location, nice bed, good shower.
Reviewed on 25 Jan 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €912, price is now €784 per person
€784
per person
2 Apr - 5 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,358, price is now €1,110 per person
€1,110
per person
3 Mar - 7 Mar
found 8 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,665, price is now €1,225 per person
€1,225
per person
14 Mar - 18 Mar
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026
The Peninsula Chicago
Downtown Chicago
Price was €1,885, price is now €1,559 per person
€1,559
per person
3 Mar - 7 Mar
found 8 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
Stay at this boutique hotel in Willowbrook. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,384 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
The room was very clean and it was a satisfying environment with an important person. The value is worth more than the price
Reviewed on 21 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (3,566 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
Excellent room. Awesome location. Great amenities.
Reviewed on 23 Jan 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge) and a 24-hour health club. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (2,267 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
Our first stay at Palmer house was a very welcoming experience. The location in downtown Chicago made everything along Michigan ave and surrounding sights easily accessible. The multiple entries were super helpful while walking around and navigating the cold (polar vortex). Ride share and even DoorDash ...
Reviewed on 25 Jan 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
