Places to stay near Skydeck Chicago

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Top-rated holiday rentals near Skydeck Chicago

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Top Guest favourite
A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.
Guesthouse in Chicago
4.99 out of 5 average rating, 893 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Guest favourite
A relaxing living area is furnished with a sectional sofa, a modern lounge chair, and a plush area rug. A mounted television is positioned above the couch, while floor-to-ceiling windows allow natural light to flood the space, complemented by dark curtains.
Condo in Chicago
4.96 out of 5 average rating, 45 reviews

Modern long-term luxury w/ spectacular view!

860sqft (80 square meters), 2 Bedroom (2nd bedroom is dedicated office; ideal for professionals), 2 full baths, 10ft. concrete ceiling loft with floor to ceiling windows in every room. You'll love my place because of the great neighborhood, dining, ease of access, and the incredibly clean and accommodating space itself. This is my home for part of the year, with intermittent and seasonal travel and is maintained as well as it would be if it was my primary residence and I am always returning.

Top Guest favourite
An outdoor pool is surrounded by a pavement area, featuring a few lounge chairs arranged along the sides. The building's modern architecture is visible in the background, with city high-rises and clear blue skies providing a vibrant setting.
Apartment in Chicago
5 out of 5 average rating, 34 reviews

The Stadium Overlook

Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city. Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 1 bedroom apartment offers guests all the comforts of home, whether on the road for work or play.

Apartment in Chicago
4.65 out of 5 average rating, 668 reviews

Sonder South Wabash | Superior 1BR Apartment

Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kitchen, in-suite laundry, and stunning Chicago views. Colorful art pieces complement the industrial exposed concrete ceilings. And floor-to-ceiling windows burst with natural night. There’s always something to do in the Windy City. Whether you like jazz, opera, or dive bar karaoke, the South Loop has entertainment for everyone. At South Wabash, experience the best of the city.

Superhost
A well-appointed guest room features two spacious beds with light-colored linens, complemented by a textured blanket. A large wall mural of a city map enhances the space, while a flat-screen TV is mounted above a dark wood console. Natural light fills the room through a nearby window.
Hotel room in Chicago
4.84 out of 5 average rating, 173 reviews

2 Queen Bedroom in Downton

Experience upscale accommodations & amenities in the heart of Chicago when you stay at Cambria Hotel. Located conveniently close to some top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services & on-site restaurant that offers classic American cuisine. Unwind & relax in our comfortable guest rooms with Chicago-inspired décor. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Guest favourite
A comfortable living area features a modern sofa, complemented by two stylish ottomans. A large window with sheer curtains provides natural light, while a wall-mounted TV is positioned for easy viewing. A piece of wall art adds a contemporary touch.
Apartment in Chicago
5 out of 5 average rating, 20 reviews

Chicago Luxury Long Term 30+

Enjoy a stylish experience at this centrally-located place. This home is a lovely city terrace modern loft in a quiet nook of the Fulton Market / West Loop Area. Furnished beautifully for working from home or coming home. Very walkable with all of the best smart home features: digital light controls, Sony 65” TV, Sonos BEAM, smart lock, solid marble dining table with modern chairs, comfortable bed and pillows, and quality sheets for a great night sleep! Ultra high speed internet at 500mbps

Superhost
A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.
Apartment in Chicago
4.74 out of 5 average rating, 341 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

The exterior of a historic four-story building showcases intricate stonework and arched windows. Two blue doors with glass inserts serve as the main entrance, framed by a wooden porch that leads to the entrance. The surrounding greenery adds a touch of nature.
Loft in Chicago
4.7 out of 5 average rating, 157 reviews

Studio with View of Skyline in Heart of Pilsen

Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heat of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. Unit is on the 4th floor, no elevator. No Private Parking, just street parking . Located near major transportation, Divvy Bike Station across the street.

Guest favourite
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Chicago
4.83 out of 5 average rating, 840 reviews

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.

Guest favourite
A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.
Apartment in Chicago
4.85 out of 5 average rating, 311 reviews

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.

Superhost
Apartment in Chicago
4.9 out of 5 average rating, 40 reviews

Downtown Luxury|Cozy Stay| Walk to Millennium Park

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!

Top Guest favourite
Apartment in Chicago
4.99 out of 5 average rating, 256 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Popular amenities for holiday rentals near Skydeck Chicago

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