Family-Friendly Vacation Rentals in Willis Tower, IL: Compare 10+ Sites & Save

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774 Best Family Vacation Rentals in Willis Tower (Starting from $115)

Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Apartment
Chicago, IL, USA
0.4k from Willis Tower center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms25 Guests
8.7

Fabulous

42 reviews

$854
Average price / night
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LIVN West Loop Chicago 1 BR
LIVN West Loop Chicago 1 BR
Apartment
Chicago, IL, 60661, United States
0.5k from Willis Tower center

AC, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Microwave

1 Bedroom2 Guests
New to Booking
$171
Average price / night
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Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Apartment
Chicago, IL, USA
0.5k from Willis Tower center

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

51 Bedrooms12 Guests
8.1

Very Good

322 reviews

$181
Average price / night
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LIVN West Loop Chicago 2 BR City View
LIVN West Loop Chicago 2 BR City View
Apartment
Chicago, IL, 60661, United States
0.5k from Willis Tower center

AC, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$228
Average price / night
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Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Apartment
Chicago, IL, USA
0.6k from Willis Tower center

Apartments, Accommodations, Serviced apartments, 3-star, Lodgings, Vacation rentals, Places to stay, Self-catering

30 Bedrooms31 Guests
7.7

Good

365 reviews

$211
Average price / night
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LIVN West Loop Chicago King Studio
LIVN West Loop Chicago King Studio
Apartment
Chicago, IL, 60661, United States
0.5k from Willis Tower center

AC, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Microwave

1 Bedroom2 Guests
New to Booking
$145
Average price / night
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Jeffjack Heated Pool Penthouse in Chicago's West Loop
Jeffjack Heated Pool Penthouse in Chicago's West Loop
Apartment
Chicago, IL, USA
0.6k from Willis Tower center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms6 Guests
7.0

Good

4 reviews

$323
Average price / night
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LIVN West Loop Chicago Queen Superior Studio
LIVN West Loop Chicago Queen Superior Studio
Apartment
Chicago, IL, 60661, United States
0.5k from Willis Tower center

AC, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Microwave

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$184
Average price / night
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Loop 2BR w Gym Doorman nr L Parks CHI-319
Loop 2BR w Gym Doorman nr L Parks CHI-319
Apartment
Chicago, IL, USA
0.6k from Willis Tower center

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

2 Bedrooms4 Guests
New to Booking
$115
Average price / night
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LIVN West Loop Chicago Classic Queen Studio
LIVN West Loop Chicago Classic Queen Studio
Apartment
Chicago, IL, 60661, United States
0.5k from Willis Tower center

AC, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Microwave

1 Bedroom2 Guests
New to Booking
$145
Average price / night
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Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
Apartment
IL, USA
0.7k from Willis Tower center

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

13 Bedrooms27 Guests
8.3

Very Good

30 reviews

$319
Average price / night
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LIVN Millennium Park Downtown Chicago Superior 1BR
LIVN Millennium Park Downtown Chicago Superior 1BR
Apartment
Chicago, IL, 60603, United States
0.9k from Willis Tower center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$171
Average price / night
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South Loop Rooftop With In & Out Parking 1
South Loop Rooftop With In & Out Parking 1
Apartment
Chicago, IL, USA
0.7k from Willis Tower center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$326
Average price / night
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LIVN Millennium Park Downtown Chicago Superior 2 BR
LIVN Millennium Park Downtown Chicago Superior 2 BR
Apartment
Chicago, IL, 60603, United States
0.9k from Willis Tower center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$235
Average price / night
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South Loop Rooftop With In and Out Parking 2
South Loop Rooftop With In and Out Parking 2
Apartment
Chicago, IL, USA
0.7k from Willis Tower center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$307
Average price / night
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LIVN Millennium Park Downtown Chicago Studio
LIVN Millennium Park Downtown Chicago Studio
Apartment
Chicago, IL, 60603, United States
0.9k from Willis Tower center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$145
Average price / night
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South Loop Rooftop With In and Out Parking 3
South Loop Rooftop With In and Out Parking 3
Apartment
Chicago, IL, USA
0.7k from Willis Tower center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
9.7

Exceptional

3 reviews

$311
Average price / night
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LIVN Millennium Park Downtown Chicago Prem Studio
LIVN Millennium Park Downtown Chicago Prem Studio
Apartment
Chicago, IL, 60603, United States
0.9k from Willis Tower center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$145
Average price / night
Check Availability
Loop 1BR w Gym Pool WD nr Financial District CHI-238
Loop 1BR w Gym Pool WD nr Financial District CHI-238
Apartment
Chicago, IL, USA
0.8k from Willis Tower center

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

1 Bedroom2 Guests
New to Booking
$274
Average price / night
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LIVN Millennium Park Downtown Chicago 1 BR
LIVN Millennium Park Downtown Chicago 1 BR
Apartment
Chicago, IL, 60603, United States
0.9k from Willis Tower center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$171
Average price / night
Check Availability
Luxury Loft Collection 01 - Terrace - River North
Luxury Loft Collection 01 - Terrace - River North
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

AC, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms12 Guests
9.8

Exceptional

18 reviews

$1493
Average price / night
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Luxury Loft Collection 03 - Terrace - River North
Luxury Loft Collection 03 - Terrace - River North
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

AC, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms12 Guests
9.0

Fabulous

9 reviews

$1457
Average price / night
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Luxury Loft Collection 02 - Terrace - River North
Luxury Loft Collection 02 - Terrace - River North
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Internet

3 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$1347
Average price / night
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Luxury Loft Collection COMBO 01/03 | Terrace
Luxury Loft Collection COMBO 01/03 | Terrace
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

AC, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

6 Bedrooms22 Guests
9.4

Superb

3 reviews

$2481
Average price / night
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Luxury Loft Collection COMBO 01/02 | Terrace
Luxury Loft Collection COMBO 01/02 | Terrace
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

AC, Balcony, Crib, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

6 Bedrooms22 Guests
10.0

Exceptional

4 reviews

$2293
Average price / night
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Luxury Loft Collection COMBO 02/03 | Terrace
Luxury Loft Collection COMBO 02/03 | Terrace
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

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

6 Bedrooms22 Guests
10.0

Exceptional

2 reviews

$2479
Average price / night
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Luxury Loft Collection 1, 2, 3
Luxury Loft Collection 1, 2, 3
Apartment
Chicago, IL, 60654, United States
1.7k from Willis Tower center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Internet

9 Bedrooms42 Guests
New to Booking
$4313
Average price / night
Check Availability

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 Willis Tower.

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Willis Tower Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 774 verified family-friendly vacation rentals in Willis Tower. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Willis Tower vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $115 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Willis Tower 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 Willis Tower 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 Willis Tower often include amenities such as Child Friendly, Wellness Facilities, and Accessibility. 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.