Cottages in South Side
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A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

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your current months are November, 2026 and December, 2026.

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A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

A dining area with a wooden table, four chairs, a sofa, and a lamp.

A living room with a sofa, a coffee table, and a TV mounted on the wall.

A modern kitchen with white cabinets, a stainless steel dishwasher, and a wooden countertop.

1. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

3.0 star property

Forest Park

The price is NZ$847

NZ$847

includes taxes & fees

16 Nov - 17 Nov

Classic Forest Park Foursquare < 1 Mi to Blue Line

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.

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Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers and top sights like Lake Michigan.

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Top reviews in South Side

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

The hotel has been reburbished beautifully. Staff have been amazing letting us hang out in the lounge waiting for our train departure. Great location, fantastic cafe next door, great bars in the area. Only a short walk to Michigan Avenue for hop on hop off bus.

Cherrie

Reviewed October 12, 2024Reviewed October 12, 2024

Hilton Vacation Club Hotel Blake Chicago

A modern hotel with a glass facade, named "Sable Hotel," located near a waterfront with boats docked.

A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

This was nice and convenient. Perfect area and everything was closed by.

Jezreel Elaine

Reviewed May 17, 2024Reviewed May 17, 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

A hotel room with a large bed, a desk, a chair, a nightstand, a lamp, and a mirror.

Chicago Lake Shore Hotel

Kenwood

10/10 Excellent

Great hotel to use as your springboard to Chicago. The hotel is in a safe area, near great eats in Hyde Park. The rooms are comfortable and the free shuttle bus in and out of downtown Chicago is the bomb. Will stay here again.

Kirsty

Reviewed October 25, 2019Reviewed October 25, 2019

Chicago Lake Shore Hotel

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Book a South Side Cottage

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for South Side cottages

1. Classic Forest Park Foursquare < 1 Mi to Blue Line

Learn more about South Side

Top reviews in South Side

Hilton Vacation Club Hotel Blake Chicago

10/10 Excellent

Explore a world of travel with Expedia