South Side Vacation Rentals from $229: Search Short-Term Rentals

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Our top choices for South Side vacation rentals

1 bedroom, desk, iron/ironing board, travel crib

Bright & Cozy 1BR Near UChicago

Hyde Park

Alan F.

$205 nightly

Jun 17 - Jun 18

Total with taxes and fees

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Brighton Park

Rachel

$263 nightly

Jun 9 - Jun 10

Total with taxes and fees

Dog-Friendly Apt w/ Yard: 10 Mi to Downtown

Woodlawn

Kali P.

$268 nightly

Jun 9 - Jun 10

Total with taxes and fees

Cozy Well-Equipped Studio Apartment

Hyde Park

pnina

$159 nightly

Jun 3 - Jun 4

Total with taxes and fees

Smart TV, fireplace, video games, DVD player

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Calumet Park

Timothy K.

$234 nightly

Jun 9 - Jun 10

Total with taxes and fees

1BR Chic Apt in Downtown Chicago

Hyde Park

$177 nightly

Jun 10 - Jun 11

Total with taxes and fees

Charming Hyde Park 1BR | Fully Furnished & Ready

Hyde Park

$196 nightly

Jun 8 - Jun 9

Total with taxes and fees

Iron/ironing board, travel crib, WiFi, bed sheets

Homey Hyde Park Studio Near UChicago

Hyde Park

Meg D.

$176 nightly

Jun 15 - Jun 16

Total with taxes and fees

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Brighton Park

Yiu S.

$237 nightly

Jun 15 - Jun 16

Total with taxes and fees

Sleek & Functional 2-Bedroom Apt

Hyde Park

Madonna A.

$200 nightly

Jun 9 - Jun 10

Total with taxes and fees

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Brighton Park

Jessica H.

$282 nightly

Jun 30 - Jul 1

Total with taxes and fees

2 bedrooms, iron/ironing board, travel crib, WiFi

Sunlit & Chic 2BR Retreat

Hyde Park

Misty H.

$245 nightly

Jun 16 - Jun 17

Total with taxes and fees

1 bedroom, iron/ironing board, travel crib, WiFi

Hyde Park 1BR Apt | Easy & Fully Equipped Stay

Hyde Park

$216 nightly

Jun 16 - Jun 17

Total with taxes and fees

Elevated Hyde Park Studio Unit on Dorchester Ave

Hyde Park

Michael

$176 nightly

Jun 15 - Jun 16

Total with taxes and fees

Near Lake and Museum • Modern • Game Area

South Shore

$593 nightly

Jun 7 - Jun 8

Total with taxes and fees

1BR in Prime Hyde Park Apartment

Hyde Park

"We enjoyed our stay in this well located apartment and appreciated the elevator to the second floor. Our host Christine was a great communicator. Cafes and restaurants are nearby within a 5 min walk. The bed was very comfortable with clean white sheets and I made use of the earplugs for the plumbing noises in the middle of the night which were mild enough not to wake up my husband. Otherwise nice and quiet. The large bedroom closet was large enough for my small suitcase to be opened up inside on...

Heidi Habicht P.

$177 nightly

Jun 10 - Jun 11

Total with taxes and fees

Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park

"Without coming off too harsh or unfair this is definitely a “get what you pay for accommodation”. I was in town for work and excited to find a reasonably priced space with good ratings and walking distance to the conference. Shame on me for not verifying the ratings. However, upon our late arrival we could not enter the building because the entrance keypad was broken. The host did respond to my message promptly, letting us know about an emergency lockbox. Once in the building we were welcomed...

Casandra K.

$188 nightly

Jun 8 - Jun 9

Total with taxes and fees

Homey Vibes 1BR Apt near Lake Michigan & UChicago

Kenwood

Jade R.

$197 nightly

Jun 8 - Jun 9

Total with taxes and fees

Perfect 1BR Spot near Attractions

Hyde Park

Candice S.

$174 nightly

Jun 8 - Jun 9

Total with taxes and fees

3BR | Complete & Well-Located Apt in Hyde Park

Hyde Park

Nicolle C.

$250 nightly

Jun 9 - Jun 10

Total with taxes and fees

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Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"The hotel itself is excellent—brand new, clean, modern, and well maintained. The amenities and overall atmosphere made for a pleasant stay. Unfortunately, our check-in experience on the evening of May 31 was disappointing. The front desk associate was on a phone call for about ~10–15 minutes while guests waited in line and did not acknowledge anyone waiting. A simple greeting or update would have gone a long way. When we finally checked in, it was difficult to get clear answers to questions about parking and Wi-Fi, and even the handwritten room number was hard to read. I was also disappointed by the booking experience. On Expedia, breakfast and parking were listed as “Available,” with no option to select them separately during booking. I assumed they were included in the room rate, so it was surprising to learn they came at an additional cost. While Expedia may use “Available” to mean “available for an extra charge,” I found that wording misleading. Travelers should not have to search through fine print to understand what is included. On a positive note, the front desk staff the next day were outstanding. They were friendly, professional, answered all of our questions, and provided helpful recommendations about the city. Overall, the property is excellent, but the check-in experience and lack of clarity around additional charges left room for improvement."

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

10/10 Excellent

"The staff at the Holiday Inn Express Midway were very friendly during our stay. The breakfast was also good, providing some different options daily with style of eggs and sides. The parking lot did fill up since there are a couple of other hotels in that section using the same lot, but we were able to still find a spot and didn’t have any problems with our car in a busy lot."

Chinatown Hotel Chicago

6/10 Okay

"I stayed at this hotel in Chinatown, and overall, it was a solid home base. The room and the bathroom were both surprisingly roomy, and there was plenty of hot water, which was great. The A/C worked all night perfectly, and the location felt safe and convenient—close enough to downtown that we walked there a couple of times (about a 60 minute walk). However, the maintenance really stands out as a weak point. It’s not that the place is neglected, but it’s clear professionals haven't done the maintenance. They honestly need to bring in a pro team to handle upkeep and maintain the facility's value. There was also a cigarette smell in some of the hallways from time to time, which wasn't ideal. Comfort was okay for the price, but a little more professional attention improve the facility."

Saratoga Motel By Capital O Near Midway Airport Chicago IL

4/10 Poor

"This will be my one & only stay at this motel. I wasn't expecting much, but I was nervous about sleeping here. Stains on the floor, walls & shower curtain left me with trepidations. The toilet was frightening because not only the toilet seat move, the ENTIRE commode did as well! Also, I've never had place that wanted to charge EXTRA for a late checkout of 2 hrs.... UNACCEPTABLE! The only good attributes are that it's near great public transportation & close the airport. Think twice before booking here..."

Jaslin Hotel

8/10 Good

"The property was within walking distance to my convention, next to China town and other amenities. I liked that there was a vending machine made available for guests as well as the water dispenser on each floor. One thing that bothered me was the windows are not double paned so I could hear the noise from cars and trucks outside and the one microwave available for guests."

Find out more about South Side

Everything you need to know about South Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $229 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for South Side vacation rentals

Bright & Cozy 1BR Near UChicago

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Dog-Friendly Apt w/ Yard: 10 Mi to Downtown

Cozy Well-Equipped Studio Apartment

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

1BR Chic Apt in Downtown Chicago

Charming Hyde Park 1BR | Fully Furnished & Ready

Homey Hyde Park Studio Near UChicago

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sleek & Functional 2-Bedroom Apt

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Sunlit & Chic 2BR Retreat

Hyde Park 1BR Apt | Easy & Fully Equipped Stay

Elevated Hyde Park Studio Unit on Dorchester Ave

Near Lake and Museum • Modern • Game Area

1BR in Prime Hyde Park Apartment

Hyde Park Trendy Studio Apartment in Good Spot

Homey Vibes 1BR Apt near Lake Michigan & UChicago

Perfect 1BR Spot near Attractions

3BR | Complete & Well-Located Apt in Hyde Park

Find vacation rentals that suit your style

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Find out more about South Side

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