South Side Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

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

    Packages with flights are ATOL protected

Top flight + Romantic hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency McCormick Place Chicago
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3 Night Romantic holidays in South Side

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Hyatt Regency McCormick Place Chicago
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See all available trips from Dublin to South Side
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4 Night Romantic holidays in South Side

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Chinatown Hotel Chicago
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See all available trips from London to South Side
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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 £554. 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

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 Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,004 reviews)

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

Travellers say...
"Not a lot of places to eat at night"

Reviewed on 19 Aug 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 Wi-Fi and free parking. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (2 reviews)
"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 Wi-Fi, a 24-hour front desk and daily housekeeping. Our guests praise the property condition in their reviews. Popular ...
5.4/10 (1,004 reviews)
"Central location and convenience to trains and restaurants"

Reviewed on 20 Aug 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.

More holidays you might like

* 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.