
Places to stay near Wintrust Arena
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Top-rated vacation rentals near Wintrust Arena
Guests agree: these stays are highly rated for location, cleanliness, and more.

Highrise Hideout (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, 121 reviews
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
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.
4.89 out of 5 average rating, 103 reviews
condo in Chicago Chinatown/McCormick
location, location, location! we are inside the Chicago Chinatown. Restaurants, grocery shops, gift shops, bakeries, boba teas is just a step a way. Transportation is very accessible. Bus line is right downstairs and redline train is within 5 min walk. McCormick, Wintrust Arena, soldier Field and Guaranteed Rate Field is just 1 mile away. Downtown, Riverwalk, magnificent miles, millennium park, museums, and attractions is around 3 miles. Midway airport is within 10 miles away.
4.9 out of 5 average rating, 78 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
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
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
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, 307 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 reviews
South Loop Condo
Large South Loop one bedroom Condo with in-unit laundry in an elevator building. Unit features tall ceilings, huge windows and open format with plenty of storage. Open kitchen with tons of cabinets and counter space. Kitchen also offers a breakfast bar. Sun-filled spacious living room with large windows. Light and bright king size bedroom. Refinished hardwoods throughout. Central air conditioning.
4.71 out of 5 average rating, 17 reviewsPopular amenities for vacation rentals near Wintrust Arena
Condo rentals with wifi

South Loop Studio Hotel (303)
4.83 out of 5 average rating, 103 reviews
Charming Condo near U.C./Loop/McCormick Place
4.81 out of 5 average rating, 219 reviews
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
4.84 out of 5 average rating, 177 reviews
Private hot tub - King bed suite - Free parking
4.92 out of 5 average rating, 282 reviews
Spacious 3BR Near McCormick Place + Transit
4.95 out of 5 average rating, 174 reviews
Secluded 2BR APT in Chinatown by McCormick/DWTN
4.83 out of 5 average rating, 201 reviews
816 PLZN LUX Apartment | Rooftop | Garage Parking
4.81 out of 5 average rating, 176 reviews
Spacious 4 Bedroom Condo
4.95 out of 5 average rating, 218 reviewsFamily-friendly house rentals

Cozy, Quiet, Riverwalk Sanctuary
4.93 out of 5 average rating, 183 reviews
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
4.95 out of 5 average rating, 467 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
Architect's Urban Oasis | 4bd/3ba I Luxe
5.0 out of 5 average rating, 132 reviews
Chicago's Bridgeport Brownstone w/Garage Parking
4.76 out of 5 average rating, 152 reviews
Luxury SOHO Styled Two-Level Townhouse - Old Town
4.93 out of 5 average rating, 164 reviews
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
4.96 out of 5 average rating, 187 reviewsApartment rentals with air conditioning

Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 249 reviews
Bright Apt In Heart of Chinatown
4.87 out of 5 average rating, 52 reviews
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 32 reviews
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 76 reviews
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 76 reviews
South Loop Studio Hotel (304)
4.85 out of 5 average rating, 71 reviews
West Loop Urban Chic Coach House
4.83 out of 5 average rating, 76 reviews
Skyline Views · Chinatown Gate · New 1BR Apartment
4.92 out of 5 average rating, 13 reviewsOther great vacation rentals near Wintrust Arena

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 36 reviews
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 61 reviews
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 16 reviews
Central 2BR South Loop Suite Near McCormick Place
4.82 out of 5 average rating, 118 reviews
Kasa | 2BD Near McCormick Place | South Loop
4.81 out of 5 average rating, 579 reviews
Modern loft w/pool table & tvs
4.94 out of 5 average rating, 32 reviews
Spacious suite w/pool table & skyline view
4.52 out of 5 average rating, 31 reviews
Sentral Premium 2BR Apt South Loop Chicago
4.67 out of 5 average rating, 370 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





