Vacation Rentals in Wintrust Arena, IL: Compare 10+ Sites & Save

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1965 Best Vacation Rentals in Wintrust Arena (Starting from $225)

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena
Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena
Apartment
Chicago, IL, USA
0.1k from Wintrust Arena center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

8 Bedrooms31 Guests
9.1

Superb

200 reviews

$225
Average price / night
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McCormick Place 2b/2b family unit with optional parking for up to 8 guests
McCormick Place 2b/2b family unit with optional parking for up to 8 guests
Apartment
Chicago, IL, 60616, United States
0.1k from Wintrust Arena center

AC, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
8.0

Good

2 reviews

$511
Average price / night
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Spacious 3BR 420 Friendly Apartment Near McCormick Place, Lakefront and Soldier Field
Spacious 3BR 420 Friendly Apartment Near McCormick Place, Lakefront and Soldier Field
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

3 Bedrooms8 Guests
8.0

Good

2 reviews

$482
Average price / night
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Spacious 5BR Luxury Suite Near McCormick Place, Soldier Field & Grant Park
Spacious 5BR Luxury Suite Near McCormick Place, Soldier Field & Grant Park
Apartment
Chicago, IL, 60616, United States
0.1k from Wintrust Arena center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1173
Average price / night
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Stylish Cozy 3BR 420 Friendly Apartment with Gym Near McCormick Place, Grant Park and Soldier Field
Stylish Cozy 3BR 420 Friendly Apartment with Gym Near McCormick Place, Grant Park and Soldier Field
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms8 Guests
7.0

Good

1 reviews

$479
Average price / night
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Spacious 2BR Apt South Loop Skyline near McCormick Place & Soldier Field
Spacious 2BR Apt South Loop Skyline near McCormick Place & Soldier Field
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms8 Guests
9.2

Superb

14 reviews

$521
Average price / night
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South Loop 3BR Group Comfort Near Downtown, Grant Park, Soldier Field and McCormick Place
South Loop 3BR Group Comfort Near Downtown, Grant Park, Soldier Field and McCormick Place
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms8 Guests
8.5

Very Good

2 reviews

$383
Average price / night
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Cozy 2BR Chicago Skyline Views Near Museum Campus & McCormick Place
Cozy 2BR Chicago Skyline Views Near Museum Campus & McCormick Place
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms8 Guests
8.0

Good

3 reviews

$508
Average price / night
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Chicago 2BR City Escape with Optional Parking Near McCormick Place, Navy Pier, Shedd Aquarium, and Millennium Park
Chicago 2BR City Escape with Optional Parking Near McCormick Place, Navy Pier, Shedd Aquarium, and Millennium Park
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$353
Average price / night
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City Views and Convenient 3BR Suite for Group of 8 Guests Near McCormick, Shedd Aquarium, Museum Campus & Navy Pier
City Views and Convenient 3BR Suite for Group of 8 Guests Near McCormick, Shedd Aquarium, Museum Campus & Navy Pier
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
6.0

Review score

1 reviews

$391
Average price / night
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South Loop 3BD 2BA Condo with Balcony and Parking
South Loop 3BD 2BA Condo with Balcony and Parking
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Balcony, Crib, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$978
Average price / night
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Modern 2BR 420 Friendly in Chicago South Loop Near Museum Campus, McCormick Place and Soldier Field
Modern 2BR 420 Friendly in Chicago South Loop Near Museum Campus, McCormick Place and Soldier Field
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms6 Guests
7.5

Good

21 reviews

$686
Average price / night
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Chic 2-bedroom apartment with WiFi, AC in lovely Chicago
Chic 2-bedroom apartment with WiFi, AC in lovely Chicago
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$262
Average price / night
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McCormick Place 420 Friendly 3BR in Downtown Chicago with Optional Parking Sleeps 8 Guests Near Soldier Field, Grant Park and Lakefront Trail
McCormick Place 420 Friendly 3BR in Downtown Chicago with Optional Parking Sleeps 8 Guests Near Soldier Field, Grant Park and Lakefront Trail
Apartment
Chicago, IL, USA
0.2k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

3 Bedrooms8 Guests
7.7

Good

16 reviews

$937
Average price / night
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Spacious 2BR Group Stay near McCormick Place & Wintrust Arena
Spacious 2BR Group Stay near McCormick Place & Wintrust Arena
House
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
9.4

Superb

6 reviews

$508
Average price / night
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Sleek and Spacious 420 friendly 3BR Retreat Near McCormick Place, Museum Campus and Soldier Field
Sleek and Spacious 420 friendly 3BR Retreat Near McCormick Place, Museum Campus and Soldier Field
Apartment
Chicago, IL, USA
0.3k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
2.5

Review score

2 reviews

$453
Average price / night
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Modern 4BR/3BA South Loop Chicago Near McCormick Place & Soldier Field
Modern 4BR/3BA South Loop Chicago Near McCormick Place & Soldier Field
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$706
Average price / night
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McCormick 2Br-2Ba for 8 guests with Optional Parking & Gym
McCormick 2Br-2Ba for 8 guests with Optional Parking & Gym
Apartment
Chicago, IL, USA
0.3k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$358
Average price / night
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McCormick Place 2BR Oasis with Patio, Gym Near Museum Campus & Soldier Field
McCormick Place 2BR Oasis with Patio, Gym Near Museum Campus & Soldier Field
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$498
Average price / night
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Spacious 2BR on Michigan Ave with Private Patio, Optional Parking & Gym Near McCormick Convention Center, Soldier Field and Grant Park
Spacious 2BR on Michigan Ave with Private Patio, Optional Parking & Gym Near McCormick Convention Center, Soldier Field and Grant Park
Apartment
Chicago, IL, USA
0.3k from Wintrust Arena center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
3.0

Review score

1 reviews

$404
Average price / night
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Stylish 2BR Apartment with Patio and Gym Near McCormick Place & Lakefront Trail
Stylish 2BR Apartment with Patio and Gym Near McCormick Place & Lakefront Trail
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.0

Good

4 reviews

$453
Average price / night
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McCormick Place 2br/2ba with optional parking that sleeps 6
McCormick Place 2br/2ba with optional parking that sleeps 6
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
New to Booking
$471
Average price / night
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Near McCormick 420 friendly 3br/2ba with Optional Parking/sleeps 8
Near McCormick 420 friendly 3br/2ba with Optional Parking/sleeps 8
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$654
Average price / night
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Stylish Cozy 3BR Smoking Friendly Unit Near McCormick Place & Museum Campus
Stylish Cozy 3BR Smoking Friendly Unit Near McCormick Place & Museum Campus
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$643
Average price / night
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Modern 2BR South Loop Gem Near McCormick Place, Navy Pier, & Adler Planetarium
Modern 2BR South Loop Gem Near McCormick Place, Navy Pier, & Adler Planetarium
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
New to Booking
$479
Average price / night
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420 friendly 3BR/2BA heaven with optional parking and sleeps 8
420 friendly 3BR/2BA heaven with optional parking and sleeps 8
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$566
Average price / night
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Modern 420-Friendly 3BR Unit Near McCormick & Lakefront
Modern 420-Friendly 3BR Unit Near McCormick & Lakefront
Apartment
Chicago, IL, 60616, United States
0.2k from Wintrust Arena center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$599
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Wintrust Arena.

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Frequently Asked Questions

You can explore 1965 verified vacation rentals in Wintrust Arena. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Wintrust Arena vary depending on the season, property size, and location. Rates typically start from around $225 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Wintrust Arena include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Wintrust Arena welcome pets. Currently, 50 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Wintrust Arena often include amenities such as Fireplace/Heating, Internet, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.