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

South Side Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for South Side vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,287 reviews)
"Nice stay"
United States
Heather
The price is P9,473
P12,948 total
includes taxes & fees
Aug 30 - Aug 31
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (21 reviews)
"Great location and super clean!"
United States
Erica
The price is P10,896
P16,656 total
includes taxes & fees
Sep 7 - Sep 8
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is P14,710
P18,804 total
includes taxes & fees
Aug 31 - Sep 1
Level Chicago – Old Town
Breakfast, lunch and dinner served

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (229 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
The price is P10,087
P11,547 total
includes taxes & fees
Aug 30 - Aug 31
The Gem Museum Suites
Interior

5. Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is P11,460
P23,542 total
includes taxes & fees
Aug 30 - Aug 31
Chicago Third Floor Studio by 747 Lofts
Living area

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very Good, (52 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is P9,798
P11,501 total
includes taxes & fees
Aug 31 - Sep 1
Wrigleyville Suites
Exterior

7. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
Interior

8. 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 P13,324
P27,700 total
includes taxes & fees
Sep 7 - Sep 8
Classic Forest Park Foursquare < 1 Mi to Blue Line
Interior

9. River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (19 reviews)
"Loved the space and location "
United States
Caroline
The price is P15,507
P22,684 total
includes taxes & fees
Sep 16 - Sep 17
River West, Third Floor Chicago by 747 Lofts
Living area

10. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is P9,031
P14,702 total
includes taxes & fees
Aug 30 - Aug 31
Ground Floor Studios in Chicago by 747 Lofts
Living area

11. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is P10,961
P17,081 total
includes taxes & fees
Sep 10 - Sep 11
Chicago Second Floor Studio by 747 Lofts
Interior

12. Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
6.0 out of 10, (2 reviews)
"The code that was provided was incorrect. I was so anxious waiting outside the building until I was lucky that other guests were out and helped me get in. I tried reaching the “24/7” line but no response until a while and they had to reset everything before I was able to get in. First and last time I will be staying here. The bed is so small for even one person and the bathroom lights felt like a ghost was there. Do not book here, your anxiety will be through the roof !"
United States
Jamila
The price is P5,817
P10,717 total
includes taxes & fees
Sep 2 - Sep 3
Cabin 105 by 747 Lofts
Exterior

13. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
Historic Oak Park Residence
Living area

14. Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home

Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home
3.0 star property
Cedar Lake
Cedar Lake 4br Home For 8 W/ Lake Views 4 Bedroom Home
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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Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"We arrived super late and the front desk was exceptional! Amazing stay! 10/10 will return to this hotel on our next visit"
Joyce 2-night trip
Posted 21 hours ago
Holiday Inn Chicago – Midway Airport S by IHG

Find out more about South Side

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