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 €1,389, price is now €1,090 per person
€1,090
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was €1,597, price is now €1,249 per person
€1,249
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was €1,562, price is now €1,225 per person
€1,225
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on 12 Mar 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was €1,561, price is now €1,300 per person
€1,300
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,016 reviews)
Nice clean room with tons of historic charm. Love the duvets and view to Millennium Park
Reviewed on 9 Mar 2026
Price found within the past 48 hours. Click for updated prices.
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €1,966, price is now €1,690 per person
€1,690
per person
14 May - 17 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was €2,042, price is now €1,784 per person
€1,784
per person
14 May - 17 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was €1,987, price is now €1,741 per person
€1,741
per person
14 May - 17 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on 12 Mar 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 ...
8.6/10 Excellent! (1,436 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
Yes, the hot tub was fine and the parking was fine too. Everything was fine.
Reviewed on 11 Mar 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! (3,608 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
Nearby Magnificent Mile.
Reviewed on 12 Mar 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 ...
8.6/10 Excellent! (2,331 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
Clean rooms, great staff, great amenities. Next to the loop and the red line. In the heart of downtown Chicago, very historic and beautiful.
Reviewed on 12 Mar 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.
