
Chicago Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to €900 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 €1,398, price is now €1,001 per person
€1,001
per person
23 Jun - 28 Jun
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Kind staff and helpful, nice rooms, wish there was a fridge in the room.
Reviewed on 27 Apr 2026

Swissotel - Chicago
Downtown Chicago
Price was €2,109, price is now €1,410 per person
€1,410
per person
23 Jun - 28 Jun
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on 27 Apr 2026



Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,853, price is now €1,310 per person
€1,310
per person
23 Jun - 28 Jun
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on 24 Apr 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! (1,489 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
Experience was amazing! I will be returning
Reviewed on 27 Apr 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! (3,670 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
The room was clean and really nice overlooking the river
Reviewed on 27 Apr 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! (2,416 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
Fabulous!
Reviewed on 27 Apr 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.
