Holiday rentals in Downtown Chicago

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Panoramic 2BR Penthouse in the Sky | 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 sunny top floor penthouse is in a perfect location with panoramic lakefront and city views in multiple directions. With over 1,300 square feet of space, 13+ foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown

Mag Mile Penthouse + Lake Views! (+Rooftop/Gym)

Welcome! Incredible Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this condo is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is generally considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier. We look forward to hosting you!

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.***

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.

Level Studio | Fulton Market

Our Level Suite, approximately 500 sqft, features an open concept studio layout with fully equipped kitchen with gas cooktop, comfortable living area, king or queen bed, storage closet, and private balcony. Many of the suites also feature designated workspaces and sofa beds. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, complimentary Wi-Fi and local calling.

Luxury South Loop Apt

Brand-new 1BR plus DEN in Chicago’s South Loop, just steps from Grant Park. Bright, modern living with floor-to-ceiling windows, plush queen bed, full kitchen, fast Wi‑Fi, smart TV, in-unit laundry, and a dedicated workspace. Walk to Millennium Park, Museum Campus, and top dining. Central heat/cool, fresh linens, essentials, 24/7 support. Five-star amenities: indoor hot tub, outdoor pool, grilling, full gym, and lounge areas. Ideal for any length of stay.

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Downtown 2BR | Lake Views + Walk to The Bean

Luxurious 2BR with breathtaking lake and Millennium Park views in historic downtown building. Sleeps 7 with king bed, queen bed, sofa bed, and air mattress. Floor-to-ceiling bay windows, 2 bathrooms, full kitchen, washer/dryer, high-speed WiFi. Walk to Millennium Park (10min), Riverwalk (5min). Building has 24-hour concierge, gym, business center. "L" train just 1 block away.

Corporate Smart Home At River Walk

Luxury smart high-rise designed for corporate stays and business travelers. This fully furnished unit features seamless smart home controls, high-speed WiFi, and a dedicated workspace for productivity and comfort. Located in the heart of downtown, steps from the river, dining, and nightlife. Ideal for professionals in town for training, projects, or short-term assignments.