Vacation Rentals in Printers Row, IL: Compare 10+ Sites & Save

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2146 Best Vacation Rentals in Printers Row (Starting from $115)

South Loop 1br w gym game room nr top schools CHI-988
South Loop 1br w gym game room nr top schools CHI-988
Apartment
Chicago, IL, USA
0.2k from Printers Row center

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

1 Bedroom2 Guests
New to Booking
$211
Average price / night
Check Availability
Go•tel Private Chicago
Go•tel Private Chicago
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

AC, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Washer

2 Bedrooms6 Guests
New to Booking
$561
Average price / night
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Kasa South Loop Chicago
Kasa South Loop Chicago
Apartment
Chicago, IL, USA
0.2k from Printers Row center

Apartments, Cheap, Accommodations, Parking, Serviced apartments, Pet-friendly, 4-star, Lodgings, Vacation rentals

41 Bedrooms24 Guests
8.6

Fabulous

323 reviews

$148
Average price / night
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Downtown Penthouse 5bd VIEWS | Parking, Gym+Pool
Downtown Penthouse 5bd VIEWS | Parking, Gym+Pool
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms14 Guests
New to Booking
$2006
Average price / night
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Lux Apts with Lake Views and Top Amenities
Lux Apts with Lake Views and Top Amenities
Apartment
Chicago, IL, USA
0.4k from Printers Row center

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

13 Bedrooms32 Guests
New to Booking
$1582
Average price / night
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Huge Downtown Penthouse #4 | Park, Museums +gym
Huge Downtown Penthouse #4 | Park, Museums +gym
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

1 Bedroom7 Guests
9.4

Superb

13 reviews

$456
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
0.4k from Printers Row center

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

2 Bedrooms6 Guests
New to Booking
$326
Average price / night
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Downtown Penthouse #5 | Vintage +gym & balcony
Downtown Penthouse #5 | Vintage +gym & balcony
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

1 Bedroom7 Guests
9.6

Exceptional

17 reviews

$453
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
0.4k from Printers Row 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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Vintage Downtown Penthouse, Safe #6 +gym&balcony
Vintage Downtown Penthouse, Safe #6 +gym&balcony
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

2 Bedrooms8 Guests
9.4

Superb

11 reviews

$452
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
0.4k from Printers Row 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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Spacious Downtown Penthouse | vintage, balcony&gym
Spacious Downtown Penthouse | vintage, balcony&gym
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

1 Bedroom7 Guests
9.6

Exceptional

15 reviews

$418
Average price / night
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Luxury on the Lake - Chicago High Rise
Luxury on the Lake - Chicago High Rise
Apartment
Chicago, IL, USA
0.4k from Printers Row center

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

1 Bedroom5 Guests
New to Booking
$258
Average price / night
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LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool
LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

9 Bedrooms16 Guests
New to Booking
$4049
Average price / night
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Sentral Michigan Avenue
Sentral Michigan Avenue
Apartment
Chicago, IL, USA
0.4k from Printers Row center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, Pet-friendly, 3-star, Lodgings, Vacation rentals

92 Bedrooms16 Guests
8.8

Fabulous

2026 reviews

$245
Average price / night
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Downtown Penthouse #1 | Vintage 2bd (+Gym)
Downtown Penthouse #1 | Vintage 2bd (+Gym)
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

2 Bedrooms6 Guests
9.2

Superb

24 reviews

$485
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 Printers Row 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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Spacious Downtwn Penthouse|Vintage 3bd-GYM+Balcony
Spacious Downtwn Penthouse|Vintage 3bd-GYM+Balcony
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

3 Bedrooms9 Guests
9.6

Exceptional

18 reviews

$656
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
0.7k from Printers Row 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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DTown Penthouse - 4bd/4ba (+Parking + Gym )
DTown Penthouse - 4bd/4ba (+Parking + Gym )
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms12 Guests
9.8

Exceptional

8 reviews

$1891
Average price / night
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South Loop 3 Bedroom Apt
South Loop 3 Bedroom Apt
Apartment
Chicago, IL, USA
0.7k from Printers Row 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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Dtown Penthouse 11+Parking, Gym, Pvt Patio
Dtown Penthouse 11+Parking, Gym, Pvt Patio
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

2 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$798
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
0.7k from Printers Row center

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

2 Bedrooms4 Guests
New to Booking
$115
Average price / night
Check Availability
DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

2 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$756
Average price / night
Check Availability
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
0.7k from Printers Row center

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

1 Bedroom2 Guests
New to Booking
$255
Average price / night
Check Availability
Sleep 14 | Downtown, Vintage 5bd/2ba (gym+patio)
Sleep 14 | Downtown, Vintage 5bd/2ba (gym+patio)
Apartment
Chicago, IL, 60605, United States
0.2k from Printers Row center

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

5 Bedrooms14 Guests
New to Booking
$1432
Average price / night
Check Availability
Downtown 3bd Penthouse| Lake Mich VIEWS +gym
Downtown 3bd Penthouse| Lake Mich VIEWS +gym
Apartment
Chicago, IL, 60605, United States
0.3k from Printers Row center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$657
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 Vacation Rentals in Printers Row.

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Frequently Asked Questions

You can explore 2146 verified vacation rentals in Printers Row. 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 Printers Row vary depending on the season, property size, and location. Rates typically start from around $115 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 Printers Row 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 Printers Row welcome pets. Currently, 64 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 Printers Row often include amenities such as Fireplace/Heating, Wellness Facilities, and Accessibility. 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.