Short-Term Rentals in Greater Grand Crossing, IL: Compare 10+ Sites & Save

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476 Best Short-Term Rentals in Greater Grand Crossing (Starting from $45)

BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12
BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12
House
Chicago, IL, USA
0.5k from Greater Grand Crossing center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

5 Bedrooms12 Guests
9.3

Superb

3 reviews

$449
Average price / night
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Spacious 4-bedroom apartment in gorgeous Chicago with AC and gym
Spacious 4-bedroom apartment in gorgeous Chicago with AC and gym
Apartment
Chicago, IL, 60619, United States
0.2k from Greater Grand Crossing center

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

4 Bedrooms9 Guests
New to Booking
$280
Average price / night
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Bluenile
Bluenile
Apartment
Chicago, IL, USA
0.7k from Greater Grand Crossing center

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

6 Bedrooms14 Guests
New to Booking
$252
Average price / night
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Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
House
Chicago, IL, 60619, United States
0.4k from Greater Grand Crossing center

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

5 Bedrooms8 Guests
8.6

Fabulous

22 reviews

$197
Average price / night
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Spacious 5-bedroom building with WiFi, AC in beautiful Chicago
Spacious 5-bedroom building with WiFi, AC in beautiful Chicago
House
Chicago, IL, 60637, United States
0.7k from Greater Grand Crossing center

AC, Dryer, Heater, Internet, No Smoking, Washer

6 Bedrooms9 Guests
New to Booking
$671
Average price / night
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Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
Apartment
Chicago, IL, USA
0.8k from Greater Grand Crossing center

Internet, Air Conditioner, Child Friendly, Laundry, Smoking, Parking, Balcony/Terrace

6 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$377
Average price / night
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NEW! Chicago Getaway with Pool Table & Modern Comfort
NEW! Chicago Getaway with Pool Table & Modern Comfort
House
Chicago, IL, 60619, United States
0.7k from Greater Grand Crossing center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Microwave, No Smoking, TV

3 Bedrooms6 Guests
New to Booking
$487
Average price / night
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Charming 3BD 2BTH Apartment
Charming 3BD 2BTH Apartment
Apartment
Chicago, IL, USA
1.0k from Greater Grand Crossing center

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

3 Bedrooms6 Guests
8.4

Very Good

8 reviews

$90
Average price / night
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Clean Comfy Space for Traveling Professionals
Clean Comfy Space for Traveling Professionals
Condo
Chicago, IL, 60637, United States
0.9k from Greater Grand Crossing center

AC, Barbecue, Dryer, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

1 Bedroom6 Guests
New to Booking
$83
Average price / night
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Chicago Apt 3 Mi to Lake Michigan!
Chicago Apt 3 Mi to Lake Michigan!
Apartment
Chicago, IL, USA
1.2k from Greater Grand Crossing center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$79
Average price / night
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Single Family Brick Home
Single Family Brick Home
Apartment
Chicago, IL, 60637, United States
1.1k from Greater Grand Crossing center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms2 Guests
New to Booking
$124
Average price / night
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Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Apartment
Chicago, IL, USA
1.3k from Greater Grand Crossing center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering, Accessible hotels

3 Bedrooms6 Guests
8.2

Very Good

11 reviews

$126
Average price / night
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Beautiful 4 bedroom 2 bath pet friendly Chicago brick bungalow
Beautiful 4 bedroom 2 bath pet friendly Chicago brick bungalow
House
Chicago, IL, 60637, United States
1.1k from Greater Grand Crossing center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms10 Guests
New to Booking
$243
Average price / night
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Chateau de Woodlawn - Room II - Le Parisienne
Chateau de Woodlawn - Room II - Le Parisienne
House
Chicago, IL, USA
1.3k from Greater Grand Crossing center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay, Self-catering

1 Bedroom2 Guests
8.4

Very Good

16 reviews

$65
Average price / night
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Woodlawn LUXE! Welcome Home! 4 bedroom condo!
Woodlawn LUXE! Welcome Home! 4 bedroom condo!
Condo
Chicago, IL, 60637, United States
1.2k from Greater Grand Crossing center

AC, Barbecue, Crib, Fireplace, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms6 Guests
New to Booking
$336
Average price / night
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Chateau de Woodlawn - Room I - La Tour Eiffel
Chateau de Woodlawn - Room I - La Tour Eiffel
House
Chicago, IL, USA
1.3k from Greater Grand Crossing center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay, Family

1 Bedroom2 Guests
9.0

Fabulous

10 reviews

$45
Average price / night
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Chateau de Woodlawn - Room III - The Dream Catcher
Chateau de Woodlawn - Room III - The Dream Catcher
House
Chicago, IL, USA
1.3k from Greater Grand Crossing center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay, Self-catering

1 Bedroom2 Guests
8.1

Very Good

30 reviews

$55
Average price / night
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Stay, Relax & Explore Chicago
Stay, Relax & Explore Chicago
House
Chicago, IL, 60620, United States
1.2k from Greater Grand Crossing center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, Microwave

2 Bedrooms10 Guests
9.0

Fabulous

6 reviews

$326
Average price / night
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Afrique Francaise de Woodlawn 1
Afrique Francaise de Woodlawn 1
House
Chicago, IL, USA
1.4k from Greater Grand Crossing center

Cheap, Accommodations, Parking, Homestays, Lodgings, Places to stay, Self-catering

1 Bedroom2 Guests
9.3

Superb

13 reviews

$76
Average price / night
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Fully furnished, modern short-term stay home near Obama Presidential Library.
Fully furnished, modern short-term stay home near Obama Presidential Library.
Apartment
Chicago, IL, 60637, United States
1.2k from Greater Grand Crossing center

AC, Dryer, Heater, Laundry, No Smoking, Washer

2 Bedrooms5 Guests
New to Booking
$282
Average price / night
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Afrique Francaise de Woodlawn 2
Afrique Francaise de Woodlawn 2
House
Chicago, IL, USA
1.4k from Greater Grand Crossing center

Cheap, Accommodations, Parking, Homestays, Lodgings, Places to stay

1 Bedroom2 Guests
8.1

Very Good

12 reviews

$76
Average price / night
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Cozy Modern, 3BRS and 1BA. 5mins from Hyde Park tourist attractions
Cozy Modern, 3BRS and 1BA. 5mins from Hyde Park tourist attractions
Apartment
Chicago, IL, 60619, United States
1.2k from Greater Grand Crossing center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
5.0

Review score

4 reviews

$544
Average price / night
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Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
Condo
Chicago, IL, 60637, United States
1.3k from Greater Grand Crossing center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$413
Average price / night
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Spacious Charming 4BD/2BTH in Woodlawn Near the University of Chicago!!!!
Spacious Charming 4BD/2BTH in Woodlawn Near the University of Chicago!!!!
Apartment
Chicago, IL, 60637, United States
1.3k from Greater Grand Crossing center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

3 Bedrooms5 Guests
8.6

Fabulous

4 reviews

$166
Average price / night
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Luxury suite with 3 Bedrooms \n10 min to downtown \n5 min to university of Chicago
Luxury suite with 3 Bedrooms \n10 min to downtown \n5 min to university of Chicago
Apartment
Chicago, IL, 60637, United States
1.3k from Greater Grand Crossing center

AC, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$252
Average price / night
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Charming Newly Updated  3-bed Chicago Apartment. Extended Stay Discount
Charming Newly Updated 3-bed Chicago Apartment. Extended Stay Discount
Apartment
Chicago, IL, 60619, United States
1.4k from Greater Grand Crossing center

AC, Barbecue, Breakfast Available, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$149
Average price / night
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Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
Apartment
Chicago, IL, 60637, United States
1.5k from Greater Grand Crossing center

AC, Dryer, Heater, Internet, Laundry, Washer

3 Bedrooms6 Guests
9.0

Fabulous

6 reviews

$255
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 Short-Term Rentals in Greater Grand Crossing.

Stay Near Greater Grand Crossing's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Greater Grand Crossing Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 476 verified short-term rentals in Greater Grand Crossing, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Greater Grand Crossing vary depending on location, property size, and travel dates. Rates typically start from around $45 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Greater Grand Crossing include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Greater Grand Crossing, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Greater Grand Crossing often include amenities such as Fireplace/Heating, Internet, and Bedding/Linens, providing a comfortable and convenient stay.

Short-term rentals in Greater Grand Crossing are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.