Family-Friendly Vacation Rentals in South Loop, IL: Compare 10+ Sites & Save

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721 Best Family Vacation Rentals in South Loop (Starting from $120)

Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Apartment
Chicago, IL, USA
0.5k from South Loop center

Apartments, Cheap, Accommodations, Serviced apartments, 4-star, Lodgings, Vacation rentals, Places to stay, Self-catering

61 Bedrooms42 Guests
8.1

Very Good

525 reviews

$167
Average price / night
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McCormick Place Spacious 3b/2b with optional parking/sleeps 10
McCormick Place Spacious 3b/2b with optional parking/sleeps 10
Apartment
Chicago, IL, 60616, United States
0.5k from South Loop center

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

3 Bedrooms8 Guests
New to Booking
$719
Average price / night
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S Loop 1BR w Gym Lounge 1 block to L CHI-525
S Loop 1BR w Gym Lounge 1 block to L CHI-525
Apartment
Chicago, IL, USA
0.6k from South Loop center

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

1 Bedroom2 Guests
New to Booking
$211
Average price / night
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Spacious 2BR Unit with Skyline View Near McCormick Place & Soldier Field
Spacious 2BR Unit with Skyline View Near McCormick Place & Soldier Field
House
Chicago, IL, 60616, United States
0.6k from South Loop center

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

2 Bedrooms8 Guests
9.4

Superb

3 reviews

$602
Average price / night
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Blueground South Loop pool golf sim nr museum CHI-1047
Blueground South Loop pool golf sim nr museum CHI-1047
Apartment
Chicago, IL, USA
0.6k from South Loop center

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

1 Bedroom2 Guests
New to Booking
$120
Average price / night
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South Loop Chicago 2BR Apartment Near Soldier Field & McCormick Place
South Loop Chicago 2BR Apartment Near Soldier Field & McCormick Place
Apartment
Chicago, IL, 60616, United States
0.7k from South Loop center

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

2 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$467
Average price / night
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South Loop 3 Bedroom Apt
South Loop 3 Bedroom Apt
Apartment
Chicago, IL, USA
0.6k from South Loop center

Fireplace/Heating, Air Conditioner, Internet, Parking, Sports/Activities, Security/Safety, Child Friendly

1 Bedroom8 Guests
New to Booking
$211
Average price / night
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McCormick Place 2b/2b corner unit with optional parking for up to 6 guests
McCormick Place 2b/2b corner unit with optional parking for up to 6 guests
Apartment
Chicago, IL, 60616, United States
0.7k from South Loop center

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

2 Bedrooms6 Guests
New to Booking
$553
Average price / night
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S Loop Studio w Pool Gym Spa nr Grant Park CHI-739
S Loop Studio w Pool Gym Spa nr Grant Park CHI-739
Apartment
Chicago, IL, USA
0.6k from South Loop center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
New to Booking
$255
Average price / night
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Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
Apartment
Chicago, IL, 60616, United States
0.7k from South Loop center

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

3 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$816
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
0.8k from South Loop 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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McCormick 6B/4Ba Luxury Suite for groups/12 guests
McCormick 6B/4Ba Luxury Suite for groups/12 guests
Apartment
Chicago, IL, 60616, United States
0.7k from South Loop center

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

6 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$1270
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
0.8k from South Loop 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 2BR with Skyline View Near Soldier Field & Museum Campus
McCormick 2BR with Skyline View Near Soldier Field & Museum Campus
Apartment
Chicago, IL, 60616, United States
0.7k from South Loop center

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

2 Bedrooms8 Guests
9.4

Superb

3 reviews

$499
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
0.8k from South Loop 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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McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
House
Chicago, IL, 60616, United States
0.7k from South Loop center

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

3 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$856
Average price / night
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Downtown Chicago 2BR Getaway South Loop Comfort Near McCormick Place, Soldier Field and Grant Park
Downtown Chicago 2BR Getaway South Loop Comfort Near McCormick Place, Soldier Field and Grant Park
Apartment
Chicago, IL, USA
0.8k from South Loop center

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

2 Bedrooms8 Guests
New to Booking
$360
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
0.7k from South Loop 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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Luxury 6BR Suite Prime South Loop Perfect Location for Families or Groups Near Soldier Field, Museum Campus & McCormick Place
Luxury 6BR Suite Prime South Loop Perfect Location for Families or Groups Near Soldier Field, Museum Campus & McCormick Place
Apartment
Chicago, IL, USA
0.8k from South Loop center

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

6 Bedrooms12 Guests
New to Booking
$779
Average price / night
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Spacious 2BR Group Retreat Near McCormick Place
Spacious 2BR Group Retreat Near McCormick Place
Apartment
Chicago, IL, 60616, United States
0.8k from South Loop center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$459
Average price / night
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Modern 3BR South Loop Living Family Unit Near Adler Planetarium & McCormick Convention Center
Modern 3BR South Loop Living Family Unit Near Adler Planetarium & McCormick Convention Center
Apartment
Chicago, IL, USA
0.8k from South Loop center

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

3 Bedrooms8 Guests
New to Booking
$320
Average price / night
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Bright 2BR Oasis Retreat near McCormick Place & Museum Campus
Bright 2BR Oasis Retreat near McCormick Place & Museum Campus
Apartment
Chicago, IL, 60616, United States
0.8k from South Loop center

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

2 Bedrooms8 Guests
4.0

Review score

1 reviews

$553
Average price / night
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McCormick Luxury 3B/2Ba Corner Oasis for up to 8 guests with optional parking
McCormick Luxury 3B/2Ba Corner Oasis for up to 8 guests with optional parking
Apartment
Chicago, IL, 60616, United States
0.8k from South Loop center

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

3 Bedrooms8 Guests
8.0

Good

2 reviews

$635
Average price / night
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Group-Friendly 2BR Chicago Retreat Near McCormick Place & Soldier Field
Group-Friendly 2BR Chicago Retreat Near McCormick Place & Soldier Field
Apartment
Chicago, IL, 60616, United States
0.8k from South Loop center

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

2 Bedrooms8 Guests
New to Booking
$514
Average price / night
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McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
Apartment
Chicago, IL, 60616, United States
0.8k from South Loop center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$637
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
0.8k from South Loop center

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

2 Bedrooms8 Guests
New to Booking
$498
Average price / night
Check Availability
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Apartment
Chicago, IL, 60616, United States
0.8k from South Loop center

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

6 Bedrooms12 Guests
9.6

Exceptional

4 reviews

$1321
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 Family Vacation Rentals in South Loop.

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South Loop Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 721 verified family-friendly vacation rentals in South Loop. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in South Loop vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $120 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in South Loop offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in South Loop are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in South Loop often include amenities such as Child Friendly, Accessibility, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.