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

Modern LOFT Ukrainian Village 2nd floor
Private, Bright 2nd floor Loft with Tall Ceilings with Lots of Light. Creative Decor with Artwork and Artifacts. Relaxing and Cozy. Tree Top View of the Garden. Everything you need for a Long or Short Time Stays. Stocked Kitchenette, Modern Bath, Laundry and Fast WI-FI . Perfect for 1 or 2 for work or play. The Street is Quiet, Conveniently Located just 1 block from Bustling Division Street in Wicker Park, Downtown, the Blueline to all Airports and 1 Mile from the New Salt Shed Music 🎵 Venue

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.

Entirely Private Suite - Urban Oasis - Pilsen/UIC
Pilsen - McCormick Place - Soldier Field - Thalia Hall - UIC - Chinatown - South Loop - Radius Welcome to a brand new, entirely private, spacious and peaceful oasis in Pilsen-UIC with a smartlock system and self check in. Central location near some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, iron, desk, coffeemaker, toiletries and a lovely private deck.

1 #12 - 2 Bedroom 1 Bath Condo - McCormick Place
Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living room and a well appointed kitchen. This premium condo has 4 beds and can accommodate 7+ guests. Minutes to Downtown, McCormick Place, and popular attractions. Walking distance to public transit, stores, Walgreens, Starbucks, and many great restaurants. We have properties here and in the vicinity that can accommodate groups of 27 or more guests. Contact us for details.

La Casita Norte
Modern Bronzeville 1-Bedroom Apartment in quiet centrally-located neighborhood close to McCormick Place, Wintrust Arena, and White Sox Park, IIT, and 31st Street Beach. Sleeps 4 with a full bed and queen living room sofa sleeper. Comfortable dedicated workspace with reliable Wi-Fi connection and morning coffee. Huge bath w/ separate shower and endless hot water, wet bar, living room, washer/dryer. Fitness room with a Bowflex machine, treadmill, Pilates reformer, yoga mats, trampoline.

Cozy Hidden Gem Near Downtown+Train+Dining+Parking
Experience one of the best neighborhoods in Chicago in this Hidden City Gem, 2BR/1bath apartment. Perfect for couples, families, or small groups. Centrally located, just minutes to downtown, CTA/L Pink Line train is one block away, Free WiFi, permit parking, cable, in-unit front load washer/dryer, highways nearby. Explore the vibrant community, art/murals, delicious food, and cultural venues. Book now for a comfortable and memorable stay in the Heart of Chicago Pilsen Neighborhood.

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.

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.

Modern 3BR with Private Rooftop & Free Parking
A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.

Chicago Living: Your Home Away From Home
Historic Landmark Frank Lloyd Wright Townhouse built in 1894. Great Location! Newly renovated private living quarters with separate entrance. This historic townhouse has the distinction of being the only townhouse designed by famed architect Frank Lloyd Wright that was ever built.

Near McCormick Place and Minutes from Downtown!
My place is close to McCormick Place, Mercy Hospital, Downtown Chicago, Chinatown. You’ll love my place because of the location. My place is good for couples, solo adventurers, and business travelers.
Popular amenities for vacation rentals near Wintrust Arena
Condo rentals with wifi

Modern Izakaya Studio in Wicker Park

Your perfect place looks like?

Welcome to the Chi! Close to Downtown

Designer Loft in Fulton Market with Parking

Private hot tub - King bed suite - Free parking

Secluded 2BR APT in Chinatown by McCormick/DWTN

Downtown Lake VIEWS, Mich Ave, Museums 2bd/2ba

Cabin 104 at 747 Lofts
Family-friendly house rentals

Division St Designer Home In Heart of Wicker Park

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

Private 3rd Floor Apartment

Cool Quiet Coach House, Private Access + Patio

Wrigleyville Southport Studio

Retro Modern Bungalow | free parking | fire pit

Centrally Located, Apt. w/ Kitch. & Parking for 4

Cozy 2 bedroom house/w garage in Skokie
Apartment rentals with air conditioning

Style, comfort, and convenience

Lavish 2BR/2BA Loft I Next to Grant Park & Museums

Kasa | Spectacular City Views | Chicago

Loop 2BR w/Lake Views | 10 min to Millennium Park

The Alton - Designer Flat by Mag Mile & the Lake

Sentral Premium 2BR Apt South Loop Chicago

Sleek 2 Bed, 2 Bath Condo in Trendy Fulton Market

Prime Bridgeport – McGuane Park
Other great vacation rentals near Wintrust Arena

Historic mini mansion!

Casa 22 Luxury & Modern 3BD 2BA Home in Skokie

Sun-Soaked West Loop Penthouse/Private Rooftop/3BA

Chicago Tropical Condo

Downtown Chicago Retreat 2BD 2BA Views Gym Rooftop

A Family Rowhouse by UChicago

Vibrant, Spacious Chinatown Home

Sunny Treetop Oasis in Roscoe Village - 1BR/1BA
Destinations to explore
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- University of Chicago
- Naval Station Great Lakes




