South Side Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
4 Night Romantic holidays in South Side
How to find a romantic South Side holiday
How can I find the best South Side vacation packages for couples?
Use our easy-to-use holiday search tools to plan your most-romantic getaway to South Side. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.
Can I book cheap South Side romantic holidays for two?
Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to South Side that start from £370. Prices and availability are subject to change. Additional terms may apply.
What should I think about when booking a South Side romantic getaway?
The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.
What should I look for in a luxury romantic holiday to South Side?
Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.
Can I book a romantic hot-tub holiday in South Side?
What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.
How can I find romantic holidays for couples in South Side that are all inclusive?
Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.
Can I book a romantic trip to South Side with free cancellation and/or flexible dates?
Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.
Why should I book my South Side romantic holiday with Expedia?
At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.
Top Romantic South Side Hotels
Hyatt Regency McCormick Place Chicago
- 11 min drive from University of Chicago
Couples like: on-site spa services, al fresco dining
"We stayed 2 nights; the 2nd day no room service; called them & asked them why we didn’t get room service, no clear explanation; after a couple of calls someone had to bring us towels. The first day we got off the elevator on our floor there were dirty towels in the hallway. Not sure how the so-called ..."
Reviewed on 25 Sept 2026
The Wheeler Mansion
- 11 min drive from University of Chicago
"Awesome stay. Close to Soldiers Field."
Reviewed on 3 Sept 2026
Chinatown Hotel Chicago
- 11 min drive from University of Chicago
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
