Apartment vacation rentals in South Loop, Chicago

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Popular amenities for South Loop, Chicago apartment rentals

Weekly apartment rentals

Guest favorite
Apartment in West Lake View
4.95 out of 5 average rating, 112 reviews

Chic retreat near the best of Lakeview & Wrigley

Sifan LydiaRating, 5 stars3 weeks ago
Nice and clean 1 bed unit for a week of comfortable stay. Thank you for hosting us!!
Guest favorite
Apartment in Wicker Park
4.94 out of 5 average rating, 108 reviews

Bright two bedroom garden apartment

AudryRating, 5 stars2 days ago
My family and I stayed for a few days and really enjoyed the unit. The place was really clean, well equipped, and was just as described. Parking was very easy to find, the neighborhood was beautiful, and within walking distance of several restaurants and coffee spots. Carol was very responsive to questions and gave excellent guidance on accessing the place. She was even kind enough to return a forgotten item to us. I would highly recommend this space and would absolutely come back again for another stay.
Guest favorite
Apartment in Lincoln Square
4.91 out of 5 average rating, 196 reviews

Comfortable Vintage North Side Retreat for 8

MichaelRating, 5 stars1 week ago
Great place in Chicago. Close to the brown line for loop access. Walkable and beautiful area
Guest favorite
Apartment in Irving Park
4.94 out of 5 average rating, 239 reviews

Cool and Modern Chicago Apartment near Transit

TessRating, 5 stars2 days ago
Our stay at Afsha's was perfect! From the booking through checkout, communication and instructions were proactive and clear. The space was incredibly clean and there were prestine linens and towels available. The kitchen had everything we needed and was organized beautifully. The location is in a thriving neighborhood and the off-street parking space was great to have in an area where parking is hard to find.
Superhost
Apartment in West Town
4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

SivaRating, 5 stars9 months ago
This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.
Guest favorite
Apartment in Wicker Park
4.85 out of 5 average rating, 172 reviews

Oasis Collection's Mid-Century 3 Bd Wicker Park.

BeckieRating, 5 stars1 month ago
This is a very clean and comfortable unit. The beds are very comfy, the comforts are wonderfully soft. Basic toiletries and kitchen essentials are provided. The location is excellent for us, as we have young grandchildren and a dog, both enjoyed wicker park. Many restaurants are close enough for walking.
Guest favorite
Apartment in Bridgeport
4.94 out of 5 average rating, 132 reviews

CitySlickers Crash Pad /Free Parking /No Clean Fee

AmberRating, 5 stars4 days ago
The ambiance of this place was magnificent. Everything you need including some awesome books. I felt great energy when I walked in the place and felt like I hit the jackpot of airbnbs. Perfect for one person, a couple or 2 couples. Definitely home away from home vibes. I wish I had booked for a longer stay but overall very relaxing place for a vacation or even a staycation.
Guest favorite
Apartment in Logan Square
4.83 out of 5 average rating, 262 reviews

BERNARD CHATEAU - LOGAN SQUARE

HyunjinRating, 5 stars2 weeks ago
it was my first Airbnb experience and it was very pleasant. The location is perfect to get to the place, but perfectly peaceful in the night.

Private apartment rentals

Guest favorite
Apartment in Oak Park
4.87 out of 5 average rating, 282 reviews

Cosmopolitan Nest in Oak Park North Side

JarawnRating, 5 stars1 week ago
Zarko's place turned out better than expected for our soccer weekend. Even without a kitchen we still were able to manage with the microwave and fridge. Nice, quiet and clean place with separate entrance. Would stay again if only 2 of us went back to Chicago.
Guest favorite
Apartment in Near North Side
4.91 out of 5 average rating, 138 reviews

Modern 3BR with Private Rooftop & Free Parking

ChunguangRating, 5 stars1 week ago
A great place to stay for a family to explore downtown Chicago. The location is convenient, with easy access to major attractions, and restaurants. The home was clean, cozy, and well-equipped — we truly felt like we were at our own home. The host was responsive and thoughtful, which made our stay even more comfortable. Highly recommended!
Guest favorite
Apartment in East Rogers Park
4.9 out of 5 average rating, 145 reviews

Private Garden Apartment GATED FREE Parking

ElaineRating, 5 stars1 week ago
Highly recommend. Peaceful, well equipped unit with a homey feel. Bed extremely comfortable, with many pillows and comfortable mattress. Elena represents the unit well. I will rent again the next time I am in Chicago.
Guest favorite
Apartment in Avondale
4.97 out of 5 average rating, 107 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

DarenRating, 5 stars1 week ago
A very nice and welcoming place to stay!
Top guest favorite
Apartment in Avondale
4.92 out of 5 average rating, 277 reviews

Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby

MeganRating, 5 stars1 month ago
Shaun and Christina's place was exactly what we were looking for. Lots of cool restaurants nearby and they were extremely helpful and communicative. Highly recommend!
Superhost
Apartment in Roscoe Village
4.76 out of 5 average rating, 259 reviews

North Side Pied-à-terre

JeanRating, 5 stars3 weeks ago
We needed a place to stay in the Roscoe Village area, and this was perfect from a location and size standpoint. It is urban-on a well traveled street, close to the metro stop, lots of coffee shops and places to eat. Appreciated the white noise machine in the bedroom and the bathroom towels were very nice. Communication was excellent and easy to understand. Highly recommend!
Guest favorite
Apartment in Evanston
4.85 out of 5 average rating, 250 reviews

Adorable 1BR apartment near Northwestern

JoshuaRating, 5 stars3 days ago
The place was exactly as shown and described. Very lovely in a very peaceful part of town. Responses to questions were always prompt and clear. One of the best. Thank you for the pleasant stay.
Superhost
Apartment in Chinatown
4.82 out of 5 average rating, 185 reviews

New apartment

Gary QilieunRating, 5 stars5 months ago
Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!

Apartment rentals with a hot tub

Guest favorite
Apartment in West Loop
4.85 out of 5 average rating, 89 reviews

Quiet but in the Heart of City walk Everywhere

ChrisRating, 5 stars1 month ago
This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.
Superhost
Apartment in Lake View
4.67 out of 5 average rating, 9 reviews

Minutes to Wrigley Amazing Location - Sleeps 6

MattRating, 5 stars6 days ago
Freddy was an incredibly friendly and responsive host, really went above and beyond to ensure a good trip. The location is perfect, just a few minute walk to everything you could want while still maintaining a quiet residential feel.
Guest favorite
Apartment in West Loop
4.96 out of 5 average rating, 24 reviews

Skyline Oasis: City & Lake Views

NatashaRating, 5 stars2 months ago
Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!
Superhost
Apartment in Chicago
4.85 out of 5 average rating, 53 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars7 months ago
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!
Superhost
Apartment in Chicago
4.82 out of 5 average rating, 11 reviews

Large Studio Apartment with no cleaning fee

MelyssaRating, 5 stars5 months ago
What a great stay! The boat was even better. He was immediately responsive and accommodated extra when caught in a pinch. He was very communicative and helpful. The place was very comfortable for both us and the dogs. It felt like home! Would recommend to anyone.
Top guest favorite
Apartment in West Town
5 out of 5 average rating, 6 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

PattyRating, 5 stars1 month ago
Avantika’s penthouse apartment was absolutely lovely. The space was comfortable and well-designed, with beautiful bedrooms and impeccably clean bathrooms. The kitchen was modern, spacious, and had everything we needed. Avantika was incredibly kind, helpful, and very responsive throughout our stay. We had a fantastic experience and will definitely be back!
Top guest favorite
Apartment in Belmont Cragin
4.98 out of 5 average rating, 108 reviews

Belmont Pleasures - hot tub / arcade gaming room

TaraRating, 5 stars1 week ago
What could I say… the place was amazing!! My grandson and his friends had a terrific time. Me and my family enjoyed the couple for days we stayed here, the amount of things you can do in the house was amazing, will definitely will be booking all my grandkids parties here.
Guest favorite
Apartment in Irving Park
4.93 out of 5 average rating, 28 reviews

2Bed 2Bath 15min to Wrigley with Parking& Balcony

KaylaRating, 5 stars2 weeks ago
Anytime I'm in Chicago you best believe this is where I'll be. Megan is a wonderful host who gives the best recommendations and is super responsive. She goes out of her way to make sure that you will have a great stay and beyond. My children left a few items behind and Megan did not hesitate to let me know and offer to mail the items to me. That's A+++ service! Her hideaway is beautiful! Great location, very clean and nicely decorated. A lot to do in the walkable area, not far from downtown and never once questioned our safety. Do yourself a favor and book a stay here, you won't be disappointed. Thanks, Megan!

Quick stats about apartment rentals in South Loop, Chicago

  • Total rentals

    360 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    15K reviews

  • Family-friendly rentals

    200 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    100 properties have a pool

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