South Side Romantic Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

How to find romantic South Side holiday packages on Expedia?

How can I book a romantic getaway in South Side?

Find your dream romantic South Side getaway on Expedia. From secluded hideaways to blissful spa treatments and charming country escapes, we’ve got it all. Just activate our “romantic” filters to uncover your ideal couple’s retreat in South Side.

How can I find cheap South Side romantic holidays?

Unveil the perfect and budget-friendly romantic getaways in South Side with Expedia. Our filters unlock countless options, ensuring a heart-pounding experience. Set budget filters to match your spending limits and sort by price to prioritise the most affordable options in your search results.

How can I select a romantic couple’s package for South Side?

In your search, you can apply search filters for South Side trip packages and sort your results to see the romantic getaway options first. With those standards, you could find amazing romantic holiday options in South Side, from winter getaways to secluded country or budget beach holidays with your loved one.

How can I find excellent romantic South Side holiday deals?

Plan your ultimate couple’s getaway in South Side with our user-friendly search tools. Opt for a hotel suite with a view worth sharing on Instagram. Cruise with the top down and feel the warm breeze in your hair with a luxury car hire. Decide on a romantic couple’s spa treatment, a beachfront candle-lit dinner, or a glamorous night out on the town.

How can I find last-minute romantic holiday deals to South Side using Expedia?

For last-minute romantic holiday package deals in South Side, enter your travel dates into the search and discover available deals. Customise your search with filters, covering amenities, price, star rating, and more to find your ideal romantic package for couples.

How can I find pet-friendly romantic getaway packages in South Side?

Refine your search with the “pet-friendly” filter to discover top pet-welcoming hotels and resorts in South Side. Experience a couple’s treatment, bask in beautiful surroundings, and revel in a pampering romantic getaway, knowing your pet is either by your side or well cared for in doggy day care.

How can I find great weekend couple’s holiday packages South Side?

Escape the weekly grind with fantastic couple’s weekend getaways in South Side. Enter your location and date preferences in your Expedia search and let us reveal hidden gems to leave you refreshed and love-struck for the week ahead.

Where can I find the most luxurious couple’s holiday packages in South Side?

Discover the ultimate luxury romantic packages in South Side with ease. Use the site’s or app’s search function to explore a range of lavish options, as well as to refine your choices by star rating and price.

Why should book I my romantic South Side holiday with Expedia?

Choose from our latest incredible deals or customise your trip in just a few clicks, with simple search and filter functions that make finding your next romantic South Side getaway easy. Plus, booking a package with Expedia could save you money, too, making a South Side holiday for couples all the more attractive.

Top Romantic South Side Hotels

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! (1,012 reviews)
"Amazing"

Reviewed on 22 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)
"It’s OK"

Reviewed on 24 Jul. 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.