Pet-friendly holiday rentals in South Loop

Large Home | Free Parking | Near Downtown

• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

Walkability · Outdoor spaces · Decor

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Pets · Walkability · Parking

MICH AVE Downtown 2bd, Grant Park Museums #25

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: Guests love staying with us because: ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ Beautiful views of Chicago ✅ Shared Rooftop Deck w Grills ✅ Central Location ✅ FAST WIFI ✅ Comfy KING beds ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

Walkability · Pets · Beach

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Walkability · Outdoor spaces · Indoor spaces

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Pets · Walkability · Biking

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.

Walkability · Pets · Check-in

Luxury Loft Collection 01 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Outdoor spaces · Walkability · Indoor spaces

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

Pets · Walkability · Value

Kasa | Views from your Private Balcony | 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.

Walkability · Pets · Indoor spaces

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Walkability · Outdoor spaces · Access

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

Walkability · Outdoor spaces · Comfort

816 PLZN Penthouse| Rooftop| Garage Parking

Welcome to your stylish retreat in vibrant PILSEN! This modern apartment offers garage parking, a rooftop with stunning views of Willis Tower, and a cozy firepit for relaxing evenings. Explore the neighborhood's murals, visit local bars like Simones, and enjoy Sunday brunch at Duseks. Catch a concert at Thalia Hall or sing your heart out at karaoke bars nearby. Experience the best of art, food, and entertainment in PILSEN – book your stay now!

Outdoor spaces · Walkability · Decor