Chicago Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €759, price is now €617 per person
€617
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Great staff and clean room, Coffee in the AM... can't ask for much more...
Great job
Reviewed on 4 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,520, price is now €1,023 per person
€1,023
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on 2 Dec 2025
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was €1,025, price is now €815 per person
€815
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,210 reviews)
Hotel is exceptional. Staff was excellent. Our corner suite has an amazing view!!
Reviewed on 7 Dec 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €928, price is now €760 per person
€760
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
Amazing location. Love this historic hotel and the included room service breakfast is one of the best I’ve ever had.
Reviewed on 8 Dec 2025
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,520, price is now €1,023 per person
€1,023
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on 2 Dec 2025
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €831, price is now €732 per person
€732
per person
15 Jan - 19 Jan
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
I love the text option for front desk assistance
Reviewed on 8 Dec 2025
Pendry Chicago
Downtown Chicago
Price was €947, price is now €813 per person
€813
per person
15 Jan - 19 Jan
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on 4 Dec 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €874, price is now €769 per person
€769
per person
15 Jan - 19 Jan
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on 8 Dec 2025
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! (1,345 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
Staff was very helpful. A little disappointed that they took out the steamroom but i still enjoyed the jetted tub.
Reviewed on 30 Nov 2025
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! (3,420 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
Great rooftop and bar options - very good location
Reviewed on 5 Dec 2025
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! (2,115 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
great stay
Reviewed on 5 Dec 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.
