Pet-friendly holiday rentals in South Side

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

2-Bed 2-Bath Apt | close to UC w/ Free Parking

Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minutes from Downtown Chicago, the West Loop, the Medical District, and public transportation, you will love your time here is Chicago. Bright & spacious interior, updated appliances, & thoughtful finishes is sure to have you feeling right at home. Whether you are coming for an event at the United Center or just want to explore our beautiful city, you will love your time at the UC Commons.

Downtown & UC Nearby · Transit at Your Door

•Steps from the Damen Pink Line •Minutes to downtown Chicago via car or train •Easy access to major expressways I‑290 and I‑55 •Near major attractions like the United Center/Chinatown/Greektown/UIC/ West Loops nightlife and the Medical District •Vibrant cultural neighborhood - experience Pilsen’s rich art scene and authentic local dining •Ceiling height approx. 6’3” - please keep in mind when reserving •Memory Foam mattress •Guests must be 25+, have a verified account, and positive reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Kasa | Explore the Neighborhood-Mag Mile | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because: -Central Location near public transit (no car needed!) -FAST WIFI -En-suite Laundry -Lake & Park are outside our front door -Comfy Queen beds -1 Closed & 1 Loft style bedroom -Shared Rooftop Deck with stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!