Pet-friendly holiday rentals in Chicago River

Explore the City from an Elegant, Urban Retreat

- Queen Size bed in the private bedroom for two guests. - Sofa Bed with Full Size mattress for the 3rd and 4th guests (light weight and easy to setup). - Additional portable twin size cot can be set up per request. - Private Bathroom has a ceiling speaker and night light. - Living Room has an HD cinema projector with 100" screen. - A private garden with a gas grill and patio dining table/chairs. - Entry gate and door are Keyless/ Secured Key-coded. - Attached Private Parking space is available per request (subject to availability). - Easy Street Parking: Street parking is zoned (Chicago Residential Zone Parking) and we provide daily zone permits for parking on the street in front of the apartment. - Garden Space offers gas grill for Summer/Fall cookout (Share with two other apartments in the building). Text or phone call for quick reply The apartment is near the popular West Loop and West Town neighborhoods and close to public transit. Downtown parks, museums, and shops are less than two miles away. There's a Divvy Bikes station and a Starbucks across the street. Short walk to public transit ("L", bus, or Divvy bikes) 1 min drive to I-90/94. Less than 2 miles to downtown parks, museums, and shopping destinations. Less than 10 min drive to Lincoln Park, Old Town, and 5 min drive to Wicker Park, and Bucktown.

Outdoor spaces · Pets · Air conditioning

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Summer/Fall 2026. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, tall ceilings, and oversized windows, this spacious unit is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two ba

Pets · Outdoor spaces · Hospitality

Rare 1BR Lincoln Park Apt, close to everything!

Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Outdoor spaces · Walkability · View

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.

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 · Shared spaces

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.

Pets · Walkability · Value

Luxury Loft Collection 02 - 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!

Walkability · Pets · Comfort

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.

Outdoor spaces · Walkability · Pool

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Walkability · Pets · Location

River North's Rock N Roll

Decorated with rock n' roll memorabilia located above a trendy restaurant. This cozy apartment also features high ceilings and a carved canopy bed. Minutes to Mag Mile and the Loop! Free parking available. Only blocks from Michigan Avenue shopping district and blocks from downtown loop. CTA Brown line station across the street. River North Art Galleries, Great Dining, Millennium Park and all that Chicago has to offer only minutes away. Wrigley Field in 15 minutes.

Walkability · Pets · Check-in

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

Pets · Outdoor spaces · Check-in

2BR Retreat with a Fireplace in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***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 · Cleanliness