South Loop featuring night scenes and street scenes

Near South Side beach rentals

We found 38 beach rentals — enter your dates for availability

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October 2025

November 2025

Explore Near South Side beach rentals

Premier Host

The Landmark; a comfy suite near McCormick Place

Sleeps 2 · 1 bedroom · 1 bathroom

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Sleeps 8 · 2 bedrooms · 1 bathroom

Top rated beach rentals - Near South Side

Premier Host

Terrific trip to Chicago

Took my 3 adult children to Chicago for 4 days. Best summer city in the world. This condo is perfectly located, incredible view, all the amenities and far better than any hotel situation. Owner was fantastic in all communications. This is exactly how VRBO should work every time. Terrific place, terrific service and great trips. Could not give a better review!

Bob F.

Stayed June 2023

Enjoyed

Property was everything as described.Perfect location. Sonia really looks after her guests, even with some fresh supplies in the fridge, and fresh bread and eggs etc. Would recommend this location, also close to the L train!

Brent N.

Stayed May 2024

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