Places to stay near Skydeck Chicago

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.

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.***

Beautifully Renovated Loft-Style Coach House

Stay at this beautifully renovated all-brick coach house in lovely Humboldt Park/West Town! Once a cigar factory in 1908, this unique space has been fully rehabbed & restored for a charming and industrial stay. Its an open-concept loft-style house, and is entirely private - no neighbors above or below you. It boasts a balcony and a large rooftop deck with gorgeous city skyline views. We are proud to be a family-owned rental and take care and pride in this special space! Welcome to Chicago!

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.

Little Italy Historic Restoration Row House

Location, location... fully rehabbed, historic 1884 row house w/2 Queen bedrooms and 2 bathrooms across from Arrigo Park in safe, quaint Little Italy. UIC campus, Rush University Medical Center and Illinois Medical District are blocks away. United Center is 17 minute walk and downtown sightseeing easily accessible by nearby public transportation. Fujitsu heating/AC units for individual comfort. Beautiful professionally maintained gardens outside your door.

Fulton Market Loft | Rooftop Fire Pit | Parking

Featured in Condé Nast Traveler and Architectural Digest. Rated top 1% of all Airbnb listings nationwide. Two-level loft in the heart of Fulton Market. Soaring ceilings, floor-to-ceiling windows, gourmet kitchen with exposed brick, 3 bedrooms, 2.5 baths, in-unit laundry, and dedicated parking. Step outside to a private rooftop terrace with fire pit and panoramic skyline views. Steps from MICHELIN-recognized Taquería Chingón and Restaurant Row.

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.

Splendid Corner 3BR in the Loop | City Views

Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fabulous city views in multiple directions. This dramatic light-filled three bedroom, two bathroom space is perfect for groups looking for a luxurious escape in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!

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.

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

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.

South Loop Studio Hotel (304)

Stay in the center of the action in this one-of-a-kind place! You’ll be within walking distance of Chicago's most iconic landmarks. ⚠️ Please Note: Our elevator is currently undergoing repairs. All guests will need to use the stairs to access the unit. We apologize for the inconvenience and appreciate your understanding as we maintain our unique space!