South Side Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Richard Remington
- 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.
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,059 reviews)
Couples like: on-site spa services, al fresco dining
Travellers say...
The room and staff were great
Reviewed on 6 Jan 2026
The Wheeler Mansion
2020 South Calumet Avenue Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Millennium Park are located ...
9/10 Wonderful! (4 reviews)
A unique place to stay near the convention centre.
Reviewed on 23 Jun 2025
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Popular attractions Soldier Field and Millennium Park are located ...
5.4/10 (1,003 reviews)
t
Reviewed on 15 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.
