
Places to stay near Skydeck Chicago
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Top-rated vacation rentals near Skydeck Chicago
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Upscale High-Rise Apt · Rooftop Pool + Views
Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Cute, Clean, Cozy Apartment in Pilsen
Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

*Entire City Apartment 1 block to Train Park Free
Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

Florence Room - 3min to CTA, Free Parking, Roomy
The Florence room is one of three rooms in the grotto. The room has a king size bed and full size sofa sleeper for a maximum guest count of 4. You will have access to the kitchen for the microwave, toaster, and stove, along with free Keurig coffee. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms.There is a private mini fridge in your room for food storage. The house is one block from the Kedzie Green line rail station.

Urban Oasis Pilsen - guest room in townhouse
Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

Teeny Tiny Bohemian Lodge - Clean & Affordable
Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Spacious Hotel Room in The Loop
Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

Cabin 205 at 747 Lofts
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

Great location. Free parking.
Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Garden on Warren
Near West Side / West Loop location, less than 10 minute walk to United Center for Blackhawks, Bulls, music, concerts, shows, and events. Close proximity to CTA Pink & Green lines, Union Park, Randolph & Fulton Street dining districts, University of Illinois at Chicago and Rush Medical District. Private entry, very secure and quiet apartment.

Cozy 1 BR, 1 Parking, Sleeps 4!
Welcome to this stunning 1-bedroom chic modern unit, featuring 1 parking space, a private entrance, and a cozy patio. With a King bed and a sofa bed, it comfortably accommodates groups and families of up to 4 guests. Just a 5-minute stroll to the lively West Loop and a quick 10-minute Uber ride to downtown restaurants, Millennium

Garden Apartment in the Historic Heart of the City
Welcome to a unique historic block in the heart of the city! Surrounded by Madison/Randolph Street night life, Little Italy, Greek Town, and the United Center, you would be surprised how peaceful this little block can be. Enjoy a serene walk in the neighborhood, or walk through to any of these great attractions.
Popular amenities for vacation rentals near Skydeck Chicago
Condo rentals with wifi

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Modern Chicago Movie Themed Apt

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

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

Unique Lincoln Park Duplex Apt

Welcoming 2BR in Chicago's Best Neighborhood!

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Lincoln Park Hideaway - 5 Min Walk to the Park!
Family-friendly house rentals

Single bedroom with Asian decor in family home

Spacious & serene in hip spot. Sleeps 4.

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Private Bed and Bathroom in a Great Location

The Blue Room

Skyline Room, near Med Ctr, Upstairs

Private Spacious Room in a shared house.

4 miles to Airport, King bed. Near expressways.
Apartment rentals with air conditioning

Chic retreat near the best of Lakeview & Wrigley

Oldtown Stylish cute studio Near Gold Coast

Loop Loft-Subway & Art Institute

Great space in West Lakeview

Logan Square Video Game Loft

Fairfield Flat, Airy Vintage Rehab

Chic Corner 2BR in the Loop | City & Lake Views

Urban Oasis in Vibrant Gold Coast
Other great vacation rentals near Skydeck Chicago

B: Spacious bedroom with private workspace.

Basement Private Studio Room

South Loop Studio Hotel (305)

A8- 6 min Walk to Pink Line

ChicagoRiver Double Room

Private living room with a Divider and sofa bed.

S6- Tiny room with twin bed

Modern design and smart amenities
Destinations to explore
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




