South Side Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
Photo by by Midway Intl Airport
- Plan, book, travel with confidence
Better together
Save up to ₹43,962 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
Top Romantic South Side Hotels
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified 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! (1,025 reviews)
Couples like: on-site spa services, al fresco dining
Travellers say...
Will be back!
Reviewed on 24 Oct 2025
The Wheeler Mansion
2020 South Calumet Avenue, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (3 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. Our guests praise the property condition in their reviews. Popular ...
5.4/10 (1,001 reviews)
Chinatown was a very beautiful area.
Reviewed on 21 Oct 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.
