
Places to stay near Wintrust Arena
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Top-rated vacation rentals near Wintrust Arena
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Large Home | Free Parking | Near Downtown
• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood
4.89 out of 5 average rating, 128 reviews
Professional's Playground (Fitness Center • Sauna)
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.
4.92 out of 5 average rating, 131 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 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.
4.72 out of 5 average rating, 192 reviews
Luxury Loft Collection 01 - 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!
4.9 out of 5 average rating, 126 reviews
Concise Comfortable Warm place free parking 3B/2Ba
-located in Chicago Chinatown. - just 5 min walk away from a bus stop(62 bus) and the CTA Red line train station. -close to Ping Tom Memorial Park, from there you can take a water taxi to enjoy the beautiful city views. -About 5 min drive to the McCormick place, Willis tower, Field Museum, Soldier field, Guaranteed rate field(White Sox), and Navy Pier. -Just 3 min walk can set your foot in the historic Old Chinatown and Chinatown Square, here you can experience Chinese food and shop.
4.9 out of 5 average rating, 105 reviews
Kasa | Explore the Neighborhood-Mag Mile | 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, 305 reviews
South Loop 3BD 2BA Condo with Balcony and Parking
Discover this modern 3-bedroom condo on Michigan Avenue, ideally situated in the South Loop, one of Chicago’s most convenient and well-connected neighborhoods. Enjoy easy access to Grant Park, Museum Campus, Soldier Field, McCormick Place, with CTA trains and buses just steps away. This walkable home features updated bathrooms and kitchen, hardwood floors throughout, a nice front deck, and an in-unit full-sized washer and dryer—perfect for families, groups, or business travelers.
4.93 out of 5 average rating, 245 reviews
1BR South Loop Loft I SuperHost + Top Rated!
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!
4.89 out of 5 average rating, 308 reviews
Blue Brick Apartment in Bridgeport - Park for Free
• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)
4.93 out of 5 average rating, 249 reviews
Spectacular Pilsen Studio for 2!
This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.
4.88 out of 5 average rating, 336 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
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 vacation rentals near Wintrust Arena
Condo rentals with wifi

Trendy Stay Thats Close to Loop, UC & McCormick Pl
4.84 out of 5 average rating, 160 reviews
South Loop Studio Hotel (303)
4.84 out of 5 average rating, 104 reviews
816 PLZN LUX Apartment | Rooftop | Garage Parking
4.81 out of 5 average rating, 176 reviews
Private hot tub - King bed suite - Free parking
4.92 out of 5 average rating, 283 reviews
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
4.84 out of 5 average rating, 177 reviews
Modern Izakaya Studio in Wicker Park
4.96 out of 5 average rating, 158 reviews
Welcoming 2BR in Chicago's Best Neighborhood!
4.85 out of 5 average rating, 365 reviews
Secluded 2BR APT in Chinatown by McCormick/DWTN
4.83 out of 5 average rating, 201 reviewsFamily-friendly house rentals

Cozy, Quiet, Riverwalk Sanctuary
4.93 out of 5 average rating, 184 reviews
Architect's Urban Oasis | 4bd/3ba I Luxe
5.0 out of 5 average rating, 132 reviews
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
4.96 out of 5 average rating, 187 reviews
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
4.95 out of 5 average rating, 467 reviews
Chicago's Bridgeport Brownstone w/Garage Parking
4.76 out of 5 average rating, 152 reviews
Peaceful Modern Full House in Trendy Bridgeport
4.95 out of 5 average rating, 318 reviews
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
4.91 out of 5 average rating, 136 reviews
Charming 3-BED in Lincoln Park/ Old Town & Parking
4.95 out of 5 average rating, 198 reviewsApartment rentals with air conditioning

Cozy & FREE parking 2BR apt in Chicago Chinatown!
4.83 out of 5 average rating, 104 reviews
Modern 1BR in Little Italy, Near West Loop
4.9 out of 5 average rating, 176 reviews
Explore Lincoln Park from a Polished Apartment
5.0 out of 5 average rating, 325 reviews
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 33 reviews
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 76 reviews
West Loop Urban Chic Coach House
4.83 out of 5 average rating, 76 reviews
Pilsen Stay | Primary King | Mins to downtown
5.0 out of 5 average rating, 3 reviews
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 76 reviewsOther great vacation rentals near Wintrust Arena

Comfy suite w/ steam shower near McCormick Place
4.92 out of 5 average rating, 85 reviews
condo in Chicago Chinatown/McCormick
4.9 out of 5 average rating, 78 reviews
Upscale High-Rise Apt · Rooftop Pool + Views
4.92 out of 5 average rating, 50 reviews
Level One Bedroom Suite | Fulton Market
4.69 out of 5 average rating, 36 reviews
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 16 reviews
Skyline 2BR in South Loop Chicago Near McCormick
4.83 out of 5 average rating, 163 reviews
Kasa | 2BD Near McCormick Place | South Loop
4.81 out of 5 average rating, 579 reviews
Modern 6BR Suite with Pool-table near McCormick
4.93 out of 5 average rating, 40 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





