
Places to stay near Skydeck Chicago
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Top-rated holiday rentals near Skydeck Chicago
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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.
5.0 out of 5 average rating, 325 reviews
Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.
4.99 out of 5 average rating, 165 reviews
Fulton House #1 (2bd/ 1ba)
Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.
4.94 out of 5 average rating, 120 reviews
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.***
4.98 out of 5 average rating, 165 reviews
Luxury Loft Collection 901 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!
4.91 out of 5 average rating, 109 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.
4.81 out of 5 average rating, 1051 reviews
Spacious 4 Bedroom Condo
Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.
4.95 out of 5 average rating, 218 reviews
Spacious 1-bedroom South Loop Loft I Sleep 5
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!
4.94 out of 5 average rating, 250 reviews
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.
4.96 out of 5 average rating, 291 reviews
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.
4.95 out of 5 average rating, 133 reviews
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!
4.86 out of 5 average rating, 159 reviews
LIVN West Loop Chicago Classic 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.
4.86 out of 5 average rating, 110 reviewsPopular amenities for holiday rentals near Skydeck Chicago
Apartment rentals with wifi

Private hot tub - King bed suite - Free parking
4.92 out of 5 average rating, 282 reviews
3-bedroom exposed brick in Chicago's Wicker Park
4.98 out of 5 average rating, 170 reviews
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
4.84 out of 5 average rating, 177 reviews
Chicago River West 4 Bedroom / 3 Bathroom
4.82 out of 5 average rating, 261 reviews
Modern Chicago Movie Themed Apt
4.88 out of 5 average rating, 229 reviews
Stunning Wicker-Park Flat with Parking!
5.0 out of 5 average rating, 185 reviews
NEW luxury Old Town 1-Bedroom condo
4.95 out of 5 average rating, 149 reviews
Old Town Condo: Private Terrace & Garage Parking
4.91 out of 5 average rating, 347 reviewsFamily-friendly house rentals

Large Home | Free Parking | Near Downtown
4.89 out of 5 average rating, 128 reviews
Architect's Urban Oasis | 4bd/3ba I Luxe
5.0 out of 5 average rating, 132 reviews
Charming 3-BED in Lincoln Park/ Old Town & Parking
4.95 out of 5 average rating, 198 reviews
Historic Old Town, Fabulous 4 Bedroom Home
4.87 out of 5 average rating, 211 reviews
Cool Quiet Coach House, Private Access + Patio
4.92 out of 5 average rating, 319 reviews
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
4.91 out of 5 average rating, 136 reviews
Private Downtown Retreat with Rooftop Oasis
4.98 out of 5 average rating, 127 reviews
Wicker Park : Stylish Comfort Meets Urban Ease
4.78 out of 5 average rating, 116 reviewsApartment rentals with air conditioning

Urban Chic Apartment by the Magnificent Mile
4.95 out of 5 average rating, 300 reviews
1BR South Loop Loft I SuperHost + Top Rated!
4.89 out of 5 average rating, 307 reviews
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 117 reviews
Modern 1BR in Little Italy, Near West Loop
4.9 out of 5 average rating, 176 reviews
Archways at the Lincoln Park Zoo 2bed/2ba
4.84 out of 5 average rating, 360 reviews
Upscale High-Rise Apt · Rooftop Pool + Views
4.92 out of 5 average rating, 49 reviews
South Loop Studio Hotel (304)
4.85 out of 5 average rating, 71 reviews
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
5.0 out of 5 average rating, 3 reviewsOther great holiday rentals near Skydeck Chicago

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 36 reviews
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 35 reviews
Luxury 4BD Gold Coast Penthouse with Deck & Views
4.97 out of 5 average rating, 39 reviews
Private rooftop | Breathtaking skyline view
5.0 out of 5 average rating, 70 reviews
Large Luxury House in River North!
4.96 out of 5 average rating, 51 reviews
Luxurious Home in Chicago Fulton Market Downtown
4.97 out of 5 average rating, 67 reviews
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 32 reviews
Large Wicker Park 6bd 4ba w/Parking-Steps to CTA
4.99 out of 5 average rating, 83 reviewsDestinations to explore
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Frank Lloyd Wright Home and Studio
- Beachwalk Vacation Rentals
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo





