Chicago Romantic Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, 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
Swissotel - Chicago
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
Fairmont Chicago at Millennium Park
Don't see what you're looking for?
See all available trips from Dublin to Chicago
View all trips
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
  • 44 min drive from Wrigley Field
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

The Champagne Lodge & Luxury Suites
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
  • 11 min drive from Wrigley Field
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

LondonHouse Chicago, Curio Collection by Hilton
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
  • 12 min drive from Wrigley Field
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

Palmer House a Hilton Hotel
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.