South Side Romantic Holidays

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to €185 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place
Hyatt Regency McCormick Place Chicago
Hyatt Regency McCormick Place Chicago
4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
  • 11 min drive from University of Chicago
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,003 reviews)

Couples like: on-site spa services, al fresco dining

Travellers say...
"Great place to stay especially with the price!"

Reviewed on 6 Jul 2025

Hyatt Regency McCormick Place Chicago
The Wheeler Mansion
The Wheeler Mansion
4 out of 5
2020 South Calumet Avenue, Chicago, IL
  • 11 min drive from University of Chicago
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (1 review)
"A unique place to stay near the convention centre."

Reviewed on 23 Jun 2025

The Wheeler Mansion
Chinatown Hotel Chicago
Chinatown Hotel Chicago
1.5 out of 5
214 West 22nd Place, Chicago, IL
  • 11 min drive from University of Chicago
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,000 reviews)
"When we checked in, we were told that we are on the 3rd foor. Problem was, no elevator. I nor my sister could keep going up and down the stairs. The good thing was that the front desk person went out of his way to put us in a 1st floor room after the 1st night."

Reviewed on 13 Jun 2025

Chinatown Hotel Chicago
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.