South Side Beach Holidays

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4 Night Beach holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel
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Find your perfect South Side beach holiday

How can I book the best beach holidays in South Side?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your South Side beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in South Side?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable South Side beach holidays, which start from £681. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in South Side?

Enjoy out-of-season seclusion on a beach holiday to South Side during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in South Side with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a South Side beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute South Side beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in South Side. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find South Side beach holidays which are all inclusive?

A beach holiday to South Side is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a South Side beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a South Side beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in South Side on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

Top Beach South Side Hotels

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! (1 review)
"A unique place to stay near the convention centre."

Reviewed on 23 Jun 2025

The Wheeler Mansion
Marriott Marquis Chicago

Marriott Marquis Chicago

4 out of 5
2121 South Prairie Avenue, Chicago, IL
  • 11 min drive from University of Chicago
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge) and 24-hour room service. Our guests praise the helpful staff ...
9/10 Wonderful! (1,000 reviews)
"Loved the stay. The view for the fireworks was amazing."

Reviewed on 11 Jul 2025

Marriott Marquis Chicago
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! (1,010 reviews)
Overall enjoyable stay, with event at Soldier Fie
"Good place to stay for a Concert at Soldier Field. By in large not bad, comfortable bed. Bathroom could have used a spot more cleaning,. Parking was not the best. Their parking lot was full, and no Valet parking. Had to park in Convention Center parking garage, with about a 15 min walk back to the ..."

Reviewed on 10 Jul 2025

Hyatt Regency McCormick Place 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.