
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, 129 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
Sunny Penthouse - Oakwood Beach
Bright top-floor 2-bedroom, 2-bath condo in Bronzeville with soaring ceilings, skylights, and abundant natural light. Unwind in the jetted tub, cook in the fully equipped kitchen, and stay connected with ultrafast AT&T Fiber internet (up to 1 Gbps)—ideal for remote work and streaming. 🌊 Just an 18-minute walk to Oakwood Beach and the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!
4.95 out of 5 average rating, 76 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, 110 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, 106 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 | Spectacular City Views | 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.
4.74 out of 5 average rating, 1408 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
West Loop Urban Chic Coach House
Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.
4.83 out of 5 average rating, 77 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, 136 reviews
LIVN West Loop Chicago Queen 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.
4.84 out of 5 average rating, 200 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, 34 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, 161 reviews
The Urban Oasis | Outdoor Lounge • Sleeps 10+
4.93 out of 5 average rating, 178 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
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
Fulton Market Loft | Rooftop Fire Pit | Parking
4.96 out of 5 average rating, 291 reviews
Welcoming 2BR in Chicago's Best Neighborhood!
4.85 out of 5 average rating, 365 reviewsFamily-friendly house rentals

Chicago's Bridgeport Brownstone w/Garage Parking
4.76 out of 5 average rating, 153 reviews
Cozy, Quiet, Riverwalk Sanctuary
4.93 out of 5 average rating, 184 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
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
4.91 out of 5 average rating, 137 reviews
The Ashlin House.
4.92 out of 5 average rating, 143 reviews
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
4.95 out of 5 average rating, 468 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
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 250 reviews
Top of River West: Luxe Penthouse for Groups
4.89 out of 5 average rating, 141 reviews
1BR South Loop Loft I SuperHost + Top Rated!
4.89 out of 5 average rating, 308 reviews
Spectacular Pilsen Studio for 2!
4.88 out of 5 average rating, 337 reviews
Fulton House #1 (2bd/ 1ba)
4.94 out of 5 average rating, 121 reviews
Spacious 1-bedroom South Loop Loft I Sleep 5
4.94 out of 5 average rating, 250 reviews
Pilsen Stay | Primary King | Mins to downtown
5.0 out of 5 average rating, 4 reviewsOther great vacation rentals near Wintrust Arena

Cozy Chicago Stay | Private Entry + Free Parking
4.99 out of 5 average rating, 69 reviews
Spacious Luxury 6BR Suite w/ Jacuzzi & Pool Table
4.79 out of 5 average rating, 116 reviews
Kasa | 2BD Near McCormick Place | South Loop
4.81 out of 5 average rating, 579 reviews
New 3BR 2 bath family home - 10 min from downtown
5.0 out of 5 average rating, 4 reviews
Studio near Downtown w/ Kitchen & gym
4.5 out of 5 average rating, 12 reviews
Spacious suite w/pool table & skyline view
4.53 out of 5 average rating, 32 reviews
Modern 2BR Unit Rooftop & Gym Near McCormick Place
4.9 out of 5 average rating, 21 reviews
Entire 2-Bedroom apartment near Chinatown
4.68 out of 5 average rating, 112 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
- University of Chicago
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Byline Bank Aragon Ballroom
- Donald E Stephens Convention Center
- Frank Lloyd Wright Home and Studio
- Beachwalk Vacation Rentals
- Washington Park Zoo





