
Places to stay near Skydeck Chicago
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Top-rated vacation rentals near Skydeck Chicago
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Oldtown Stylish cute studio Near Gold Coast
Welcome to our stylish studio unit nestled in the heart of the city's charming old town area! This cozy space is perfect for solo travelers or couples seeking a comfortable retreat. The studio boasts a spacious bathroom, providing ample room for relaxation after a day of exploring.With its central location, you'll have easy access to the city's vibrant attractions, trendy cafes, and historic landmarks. Our studio unit offers the perfect blend of convenience and comfort for your stay in the city.

The Downtown Oasis (2BD / 2BA)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. 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.

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln
Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

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 Heart 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 only . Located near major transportation, Divvy Bike Station across the street.

*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 & 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.

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.

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!

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!

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.

Chic retreat near the best of Lakeview & Wrigley
Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

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
Popular amenities for vacation rentals near Skydeck Chicago
Condo rentals with wifi

Modern Izakaya Studio in Wicker Park

Luxe 2BR Cozy Suite | Skyline Views near McCormick

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

NEW luxury Old Town 1-Bedroom condo

The Urban Oasis | Outdoor Lounge • Sleeps 10+

3D Tour! Designer Condo near Logan Square

Private hot tub - King bed suite - Free parking

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)
Family-friendly house rentals

Single bedroom with Asian decor in family home

Caroline’s room/Private Room/Lincoln Park

Private Logan Square Garden Apt

Private Bed and Bathroom in a Great Location

The Blue Room

Florence Room - 3min to CTA, Free Parking, Roomy

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

Chicago Loop /United Center/Train -Park Free
Apartment rentals with air conditioning

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

Modern Apt with style & comfort in Pilsen Chicago

Spacious & private! Free parking! Great location!

King Bed • No Stairs • Ping-Pong • United Center

Spectacular 2BR Penthouse in the Loop | Roof Deck

WESTERN AVE ARTISTS LOFTS- Park Free

Chicago Modern Condo 2BR2BA, Balcony, Free Park

Downtown & UC Nearby · Transit at Your Door
Other great vacation rentals near Skydeck Chicago

G1. Next to Downtown! Best location

South Loop Studio Hotel (305)

A6- 6 min Walk to Pink Line

Master BR w/ensuite (600 Sq Ft.) in Chicago Condo

ChicagoRiver Double Room

Urban Oasis Pilsen - guest room in townhouse

Chicago River Room near Resurrection Med Ctr

A polished, modern affair on iconic Michigan Ave.
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
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- The Beverly Country Club
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Family travel hub Tips and inspiration
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