
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
Designer Garden Unit in Bridgeport
Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare
4.97 out of 5 average rating, 76 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
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, 1052 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 Stay | Primary King | Mins to downtown
Welcome to your stylish 2-bedroom, 2-bath retreat in the heart of Pilsen, one of Chicago’s most vibrant neighborhoods. Enjoy colorful murals, amazing restaurants, coffee shops, bars, galleries, and local boutiques—all within walking distance. The open-concept space offers comfort and style, with a fully equipped kitchen. The primary bedroom features a king-size bed and private bathroom. Downtown Chicago and top attractions are just minutes away.
5.0 out of 5 average rating, 3 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, 135 reviews
Stylish Hyde Park/Kenwood Brownstone Garden Apt
Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.
5.0 out of 5 average rating, 33 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)
4.84 out of 5 average rating, 105 reviews
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
4.84 out of 5 average rating, 177 reviews
Trendy Stay Thats Close to Loop, UC & McCormick Pl
4.84 out of 5 average rating, 160 reviews
Private hot tub - King bed suite - Free parking
4.92 out of 5 average rating, 283 reviews
816 PLZN LUX Apartment | Rooftop | Garage Parking
4.81 out of 5 average rating, 176 reviews
Secluded 2BR APT in Chinatown by McCormick/DWTN
4.83 out of 5 average rating, 201 reviews
Welcoming 2BR in Chicago's Best Neighborhood!
4.85 out of 5 average rating, 365 reviews
Fulton Market Loft | Rooftop Fire Pit | Parking
4.96 out of 5 average rating, 291 reviewsFamily-friendly house rentals

Cozy, Quiet, Riverwalk Sanctuary
4.93 out of 5 average rating, 184 reviews
Chicago's Bridgeport Brownstone w/Garage Parking
4.76 out of 5 average rating, 153 reviews
Peaceful Modern Full House in Trendy Bridgeport
4.95 out of 5 average rating, 318 reviews
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
4.96 out of 5 average rating, 187 reviews
Architect's Urban Oasis | 4bd/3ba I Luxe
5.0 out of 5 average rating, 132 reviews
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
4.91 out of 5 average rating, 136 reviews
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
4.95 out of 5 average rating, 467 reviews
Charming 3-BED in Lincoln Park/ Old Town & Parking
4.95 out of 5 average rating, 198 reviewsApartment rentals with air conditioning

LIVN West Loop Chicago Classic Studio Apartment
4.86 out of 5 average rating, 110 reviews
Explore Lincoln Park from a Polished Apartment
5.0 out of 5 average rating, 325 reviews
Spacious 1-bedroom South Loop Loft I Sleep 5
4.94 out of 5 average rating, 250 reviews
Quaint Comfort Studio Near Downtown/Queen Bed
4.99 out of 5 average rating, 288 reviews
Modern Corner 2BR in Streeterville | Roof Deck | L
4.77 out of 5 average rating, 217 reviews
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 76 reviews
West Loop Urban Chic Coach House
4.83 out of 5 average rating, 76 reviews
Front Row to the Lake & Skyline: Epic 60th Flr 3BR
5.0 out of 5 average rating, 47 reviewsOther great vacation rentals near Wintrust Arena

Comfy suite w/ steam shower near McCormick Place
4.9 out of 5 average rating, 86 reviews
Cozy Chicago Stay | Private Entry + Free Parking
4.99 out of 5 average rating, 69 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 loft w/pool table & tvs
4.94 out of 5 average rating, 32 reviews
New 3BR 2 bath family home - 10 min from downtown
5.0 out of 5 average rating, 3 reviews
Luxury penthouse with city views
5.0 out of 5 average rating, 3 reviews
Modern 2BR Unit Rooftop & Gym Near McCormick Place
4.9 out of 5 average rating, 21 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





