
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.

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

Modern 2BR South Loop Apt, McCormick & Wintrust
Modern 2BR 2 Full bath South Loop Apt | Walk to Lake, Museums, Aquarium | Pool, Gym, WiFi, Parking. Experience Chicago at its best from this stylish 2-br apartment, perfectly located across from McCormick Place and Wintrust Arena. Enjoy easy walks to the Lakefront, Field Museum, Shedd Aquarium, and Museum Campus. Amenities include: • Resort-style pool and fitness center • High-speed WiFi, CTA Access. Perfect for business travelers, families, or anyone looking to explore the heart of Chicago.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

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.

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.

South Loop 3BD 2BA Condo with Balcony and Parking
Stay in the heart of Chicago’s South Loop at this spacious 3-bedroom, 2-bath condo on Michigan Avenue. Enjoy easy access to Grant Park, Museum Campus, Soldier Field, McCormick Place, and the Lakefront Trail, with CTA trains and buses just steps away. This modern, walkable home features updated bathrooms and kitchen with new fixtures, hardwood floors throughout, a nice front deck, and an in-unit full-sized washer and dryer—perfect for families, groups, or business travelers.

Luxéry Stay "Chicago" - McCormick & Wintrust Area
Staying in one of Chicago's Historical Buildings, you can now experience living in the famous South Loop neighborhood conveniently located across from McCormick Place! South loop has a teeming restaurant scene with front row access to Grant Park, the lakefront Museum Campus and Soldier Field! this area is unmatched by most urban neighborhoods. Explore the celebrated jazz clubs, and other historic areas like industrial Motor Row and the charming Prairie Avenue District.

Lovely 1-bedroom serviced apartment near Museums!
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!

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.

Comfy suite w/ steam shower near McCormick Place
Welcome to the landmark! Our well appointed studio space is situated in the historic Calumet-Giles-Prairie District; minutes from McCormick Place, Sox Park, Wintrust Arena, IIT, and downtown. Walk to 31st St Beach, bike to Museum Campus. Perfect for business or leisure; enjoy steam shower, Wi-Fi, smart TV, and full kitchen. Easy access to major highways and public transit. We also offer a Honda Accord rental car on Turo for your convenience upon inquiry.

Bright & Spacious Boho Oasis: A Warm Retreat
Discover a sun-drenched sanctuary that feels like a hidden gem. This isn't just a place to stay; it’s an airy, open-concept retreat designed for those who want to settle right in. With high ceilings and a "Modern Boho" aesthetic, the space is flooded with natural light and a warm, inviting ambiance. Nestled in a quiet, residential pocket of West Town, you’ll enjoy peaceful surroundings with the professional service of a 5-star host.

Designer Loft in Fulton Market with Parking
Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.
Popular amenities for vacation rentals near Wintrust Arena
Condo rentals with wifi

816 PLZN Luxury Apartment| Rooftop| Garage Parking

Lovely top floor 2BR/2BA, steps from everything!

Modern Izakaya Studio in Wicker Park

Your perfect place looks like?

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Secluded 2BR APT in Chinatown by McCormick/DWTN
Family-friendly house rentals

Division St Designer Home In Heart of Wicker Park

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

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3 bed/2 bath by United Center w/ private parking

Entire house in Lakeview with yard and garage

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

Cozy garden apartment historic Jackson Bvld.

My Cozy Casa in Pilsen
Apartment rentals with air conditioning

LIVN West Loop Chicago Queen Studio Apartment

Gold Coast Luxury: 2BR with Sweeping City Vistas

Sunny Penthouse - Oakwood Beach

Upscale High-Rise Apt · Rooftop Pool + Views

Post-Punk & Industrial Museum Apt - 4BR Bridgeport

Concise Comfortable Warm place free parking 3B/2Ba

Plymouth Collection: 2BD High Floor w/ Gym,Rooftop

Cozy & FREE parking 2BR apt in Chicago Chinatown!
Other great vacation rentals near Wintrust Arena

Stylish 2BR Near McCormick |Rooftop, Gym & Parking

CasaNova Modern City Living

Bronzehaus - near McCormick, UChicago & Downtown

Loft w/4K TV, smart kitchen & 250 Mbps Wi‑Fi

2BR City Suite Near Soldier Field w/ Rooftop & Gym

Kasa | Studio, Walk to Grant Park | South Loop

Vibrant, Spacious Chinatown Home

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Destinations to explore
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Indiana Dunes State Park





