
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

Cozy Beauty Sleeps 5 - 10 Min to Downtown PacMan
Luxurious 550 sqft 1BR 1BA located 10 min from Downtown! Stand up shower, games for adults & kids, cozy bedroom 2 Smart TVs, free wifi (600 mpbs speed) Grill + Patio Chairs Sleeps 4 comfortably, 1 full bed, 1 queen sleeper sofa, 1 air mattress Street parking can be very difficult!!! - permits provided Walking distance from famous 26th street, plenty of restaurants 3 miles from Little Italy and Chinatown 15 min drive from Millenium Park and Soldier Field Great for professionals and travelers.

*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

Bright Cozy Modern-Chic Condo in Trendy West Town
Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Dapper Uptown Studio near the Lake
Welcome to this beautifully renovated, 200 sq ft studio located in the Uptown neighborhood. This apartment has access to a shared fitness area, backyard/garden, and comfy work station. The building is a block from the Red Line train and is walking distance to neighborhood restaurants, bars, shops, and cafes. This apartment is perfect for remote workers or solo travelers looking to be in a nice neighborhood close to the city! Check in is completely contactless with a keypad & door code.

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.

The Modern Retreat: 1BR|Near City|Free Parking
Located just a few blocks from Downtown Chicago, The Loop, and major attractions, this property is the perfect spot for your stay! Thoughtfully designed and fully furnished, the unit includes great amenities for your comfort and entertainment: -Fully equipped kitchen -In-unit laundry -Roku TV in the bedroom (need your own Netflix/Hulu login) -Fast WiFi speeds Ideal for healthcare workers, corporate employees, and all travelers looking for a convenient and cozy place to stay!

Cozy& Spacious 1BR unit overlooking downtown
Elevator access, 45th floor with an amazing view Smart TV, fast Wi-Fi, work-friendly space Washer/dryer in the building Stay warm and connected in the heart of Chicago’s Loop. Just steps from the Christkindlmarket, Millennium Park, and top restaurants. Perfect for travelers and families exploring the city this winter. This Bright /Airy unit has 1 California king bed, 1 large sofa that could be use as another bed and 1 airbed so you can stay with your family or friends!

Cozy newly renovated apartment in Bridgeport
Welcome to your perfect home away from home in Bridgeport, Chicago 🏡 This newly renovated cozy 1-bedroom, 1-bathroom apartment offers a comfortable, inviting space just 10 mins to downtown Chicago. Located couple minutes from Chinatown Whether you're here to catch a White Sox game or immerse yourself in the vibrant local food scene and culture, this location is ideal for exploring the best of Chicago. FREE PARKING 🅿️ NO PARTIES.

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!

Cozy Coach House Retreat Near Downtown!
Fully remodeled coach house centrally located in Chicago! Most tourist attractions are within a 15 drive or less! Public transportation is within a 3 min walk. You'll also have access to the shared rooftop deck (Furniture available May 5th-Sept 30th). This cozy unit offers 1 Queen bed + 1 bath, 1 Queen size air mattress provided, fully stocked kitchen and spacious living room space! Free Street Parking in the Area

Urban Comfort in the Heart of Chicago
This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.
Popular amenities for vacation rentals near Skydeck Chicago
Condo rentals with wifi

Charming Condo near U.C./Loop/McCormick Place

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

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Welcome to the Chi! Close to Downtown

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

Unique Lincoln Park Duplex Apt

Wicker Park/Bucktown condo with large balcony

Welcoming 2BR in Chicago's Best Neighborhood!
Family-friendly house rentals

Egyptian Room - Free Parking, 1 block to CTA

Garden/unit/1+1/cosy

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

S3 Private cozy room. NO parking. 15min to O'Hare

Spacious private room/ private bath in modern home
Apartment rentals with air conditioning

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

LairBnB - Garden Apartment

Cute, Clean, Cozy Apartment in Pilsen

Oldtown Stylish cute studio Near Gold Coast

Sunny 1BR Walk-Up Bridgeport | Easy Street Parking

Loop Loft-Subway & Art Institute

Great space in West Lakeview

Quirky Quarters at Wrigley
Other great vacation rentals near Skydeck Chicago

A+ location by Mag Mile, views, large sunny room

Cozy 1BR in South Loop | Convenience in the City

A8- 6 min Walk to Pink Line

ChicagoRiver Double Room

Stylish 1BR in West Loop

Sweeping skyline views from the 40th floor

Urban Oasis Pilsen - guest room in townhouse

Cozy private bedroom in Lakeview East, Chicago!
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




