South Side Vacation Rentals : Search Short-Term Rentals

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Our top choices for South Side vacation rentals

Sentral Michigan Avenue

Downtown Chicago

JAVIER

NT$6,629 total

includes taxes & fees

Jul 1 - Jul 2

The Gem Museum Suites

Downtown Evanston

Anton

NT$8,178 total

includes taxes & fees

Jul 12 - Jul 13

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Kimberly

NT$9,303 total

includes taxes & fees

Jun 30 - Jul 1

The Oak Park Loft

Oak Park

Linda

NT$10,021 total

includes taxes & fees

Jun 30 - Jul 1

Wrigleyville Suites

Lakeview

Kate

NT$7,443 total

includes taxes & fees

Jun 30 - Jul 1

Cabin 105 by 747 Lofts

West Town

"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 !"

Jamila

NT$11,841 total

includes taxes & fees

Jul 24 - Jul 25

Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Oak Park

Janette

NT$11,221 total

includes taxes & fees

Jul 28 - Jul 29

Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Oak Park

Ann-Marie

NT$12,131 total

includes taxes & fees

Jul 5 - Jul 6

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Top South Side Hotel Reviews

Chicago Marriott Midway

10/10 Excellent

"My room smelled so good when I came in and was the cleanest room I have stayed in in a very very long time. The carpet was even clean and did not feel sticky or anything."

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good

"The property is clean and quiet. The front desk staff was nice. The hotel was very disorganized though. I was checked into someone else’s room. My key open the door to a room with other people’s belongings.Went back down and was assigned a new room. Front desk staff mentioned, they accidentally assigned others to already occupied rooms twice that day before me. Early the next morning housekeeping was knocking aggressively on my door asking if I was checking out ( this was at 8:00 am well before 11 am check out). Happened the early the next morning too. Both days I had the do not disturb sign on my door. Seems as if hotel has a hard time tracking who is staying where and for how long."

Chicago Lake Shore Hotel

8/10 Good

"I had asked for a roll away bed, as we had 3 adults. One was only staying for 1 night and we needed that bed for that night. The bed wasn’t delivered, and there was only 1 person on staff, and that was the check-in person. Needless to say we didn’t get the bed delivered. Luckily, the guy with us always has a blow up mattress in his trunk as he camps frequently. The bed was delivered the next day while we were gone, but we didn’t need it any longer. Our room wasn’t cleaned that day, which was an issue, but I didn’t say anything. We were too tired after our busy day to even care. The next morning was checkout. We slept until 10:45, and when I called to ask what time checkout was, was told it was 11a. The desk person was gracious enough to give us until 12 noon, since we had just gotten up. We turned in our parking papers, and room keys with 10 minutes to spare. All in all, it was a pleasant stay. I would stay again. OHHH-the hotel does put a $100 charge on your card for incidentals-and I used my debit card, which takes 7-14 days for the charge to fall off and be returned. That wasn’t told to me in advance, and limited my spending. I know now to ask when I book anywhere."

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"All of the above were GREAT. I'd stay next time in town. The manager goes around and checks on things. Keeps the employees straight. Daisy at the counter was helful when I called with questions and all were very helpful suggesting restaurants and such. Although I missed not having a coffee maker in the room, the frech ground machines in the lobby more that made up for it. Never saw that anywhere else. Buffett food was good and she kept it fresh, clean and stocked. I told her too."

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"Wow! What a great experience this was. I love how when I walked in the hotel I immediately saw smiling faces and a poster of President Obama in the corner. It was right on brand for my stay as I was visiting the Obama Presidential Center for the Grand Opening weekend. The breakfast was delicious and I love that we had a space to park at the hotel. This hotel was convenient for my commute in Hyde Park. I will be back. Thank you, staff for your service and kind hospitality!"

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Check prices for these dates

Our top choices for South Side vacation rentals

Sentral Michigan Avenue

The Gem Museum Suites

Level Chicago – Old Town

The Oak Park Loft

Wrigleyville Suites

Cabin 105 by 747 Lofts

Historic Oak Park Home

Historic Oak Park Residence

At Home in Oak Park

Ground Floor Studios in Chicago by 747 Lofts

Find vacation rentals that suit your style

Top South Side Hotel Reviews

Chicago Marriott Midway

Holiday Inn Chicago – Midway Airport S by IHG

Chicago Lake Shore Hotel

Best Western Inn & Suites - Midway Airport

Jaslin Hotel

Sophy Hyde Park

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Carlton Inn Midway

Hyatt Place Chicago-South/University Medical Center

Find out more about South Side

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