Family-Friendly Vacation Rentals in Wood Street Gallery, IL: Compare 10+ Sites & Save

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808 Best Family Vacation Rentals in Wood Street Gallery (Starting from $187)

Wicker Park 4bd 3ba, Steps from CTA, Parking Incl home
Wicker Park 4bd 3ba, Steps from CTA, Parking Incl home
House
Chicago, IL, USA
0.1k from Wood Street Gallery center

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

4 Bedrooms7 Guests
New to Booking
$899
Average price / night
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Modern 1-bedroom apartment with 1 FREE Parking, Whirlpool bathtub,Full Kitchen
Modern 1-bedroom apartment with 1 FREE Parking, Whirlpool bathtub,Full Kitchen
Apartment
Chicago, IL, 60622, United States
0.2k from Wood Street Gallery center

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

1 Bedroom4 Guests
New to Booking
$632
Average price / night
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Wicker Park 6bd 4ba, Steps from CTA, Parking Incl home
Wicker Park 6bd 4ba, Steps from CTA, Parking Incl home
House
Chicago, IL, USA
0.1k from Wood Street Gallery center

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

6 Bedrooms12 Guests
New to Booking
$717
Average price / night
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:: The Wolcott ::  Modern Elegance at Its Finest
:: The Wolcott :: Modern Elegance at Its Finest
House
Chicago, IL, 60622, United States
0.2k from Wood Street Gallery center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms16 Guests
9.4

Superb

14 reviews

$3542
Average price / night
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Quiet Comfort in the Big City, Just Steps to the Blue Line apts
Quiet Comfort in the Big City, Just Steps to the Blue Line apts
Apartment
Wood Street Gallery, Chicago, Illinois, USA
0.1k from Wood Street Gallery center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$892
Average price / night
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Designer-renovated house in the heart of Wicker Park
Designer-renovated house in the heart of Wicker Park
House
Chicago, IL, 60622, United States
0.4k from Wood Street Gallery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
New to Booking
$1027
Average price / night
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4BR Near Downtown & Wicker Park - Bosworth 2
4BR Near Downtown & Wicker Park - Bosworth 2
Apartment
Chicago, IL, USA
0.6k from Wood Street Gallery center

Air Conditioner, Internet, Fireplace/Heating, Security/Safety, Pet Friendly, Child Friendly

4 Bedrooms10 Guests
New to Booking
$688
Average price / night
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LUX 3-Level Chicago Home +garage & patio
LUX 3-Level Chicago Home +garage & patio
House
Chicago, IL, 60622, United States
0.5k from Wood Street Gallery center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$965
Average price / night
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Relax in Winter Park - You Will LOVE the Garden Access and the Classic, Comfortable Feeling apts
Relax in Winter Park - You Will LOVE the Garden Access and the Classic, Comfortable Feeling apts
Apartment
Wood Street Gallery, Chicago, Illinois, USA
0.6k from Wood Street Gallery center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$335
Average price / night
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Wicker Park 4BD Home with Theater Room & Rooftops
Wicker Park 4BD Home with Theater Room & Rooftops
House
Chicago, IL, 60622, United States
0.5k from Wood Street Gallery center

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

4 Bedrooms13 Guests
New to Booking
$1321
Average price / night
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Spacious & Stylish Home at the heart of Wicker Park
Spacious & Stylish Home at the heart of Wicker Park
Apartment
IL, USA
0.7k from Wood Street Gallery center

Apartments, Accommodations, Lodgings, Places to stay

4 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$434
Average price / night
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Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
House
Chicago, IL, 60622, United States
0.5k from Wood Street Gallery center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Heater, Internet, Kitchen

4 Bedrooms23 Guests
10.0

Exceptional

12 reviews

$1711
Average price / night
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NEW! Spacious Art Deco Modern 5 BD/3BA Condo
NEW! Spacious Art Deco Modern 5 BD/3BA Condo
Apartment
Chicago, IL, USA
0.7k from Wood Street Gallery center

Air Conditioner, Barbecue/Outdoor Cooking, Balcony/Terrace, Parking, Internet, Guest Services, Security/Safety

5 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$580
Average price / night
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EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
House
Chicago, IL, 60622, United States
0.6k from Wood Street Gallery center

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

4 Bedrooms12 Guests
9.0

Fabulous

24 reviews

$1003
Average price / night
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Stylish 2BR stunner in unbeatable location
Stylish 2BR stunner in unbeatable location
Apartment
Chicago, IL, USA
0.7k from Wood Street Gallery center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$193
Average price / night
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Luxury Designer Penthouse Loft | Sleeps 20
Luxury Designer Penthouse Loft | Sleeps 20
Apartment
Chicago, IL, 60622, United States
0.7k from Wood Street Gallery center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms20 Guests
9.2

Superb

12 reviews

$1165
Average price / night
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Amazing Penthouse Skyline Views!
Amazing Penthouse Skyline Views!
House
Chicago, IL, USA
0.7k from Wood Street Gallery center

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

3 Bedrooms14 Guests
New to Booking
$1237
Average price / night
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Beautiful, cozy, stylish Bucktown, Wicker Park House, perfect Chicago location.
Beautiful, cozy, stylish Bucktown, Wicker Park House, perfect Chicago location.
House
Chicago, IL, 60622, United States
0.8k from Wood Street Gallery center

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

3 Bedrooms10 Guests
New to Booking
$902
Average price / night
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Wicker Park Flat with FREE Early Check-In & Late Checkout
Wicker Park Flat with FREE Early Check-In & Late Checkout
Apartment
Chicago, IL, USA
0.7k from Wood Street Gallery center

Security/Safety, Internet, Parking, Air Conditioner, Pet Friendly, Guest Services, Child Friendly

1 Bedroom2 Guests
New to Booking
$187
Average price / night
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Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
House
Chicago, IL, 60622, United States
0.8k from Wood Street Gallery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

89 reviews

$534
Average price / night
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Trendy Wicker Park Loft with Parking
Trendy Wicker Park Loft with Parking
House
Chicago, IL, USA
0.8k from Wood Street Gallery center

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

3 Bedrooms8 Guests
1.0

Review score

1 reviews

$504
Average price / night
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UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
House
Chicago, IL, 60622, United States
0.8k from Wood Street Gallery center

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

4 Bedrooms12 Guests
9.8

Exceptional

14 reviews

$1027
Average price / night
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Loft8 - Unique Design in Prime Location
Loft8 - Unique Design in Prime Location
Apartment
Chicago, IL, 60647, United States
1.2k from Wood Street Gallery center

AC, Crib, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$914
Average price / night
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NEW LUXURY CONDO WITH PATIO DECK
NEW LUXURY CONDO WITH PATIO DECK
Condo
Chicago, IL, 60622, United States
1.3k from Wood Street Gallery center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, Outdoor Space

1 Bedroom5 Guests
10.0

Exceptional

193 reviews

$392
Average price / night
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Wicker Park Home: Movie Room, Piano
Wicker Park Home: Movie Room, Piano
Condo
Chicago, IL, 60622, United States
1.4k from Wood Street Gallery center

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

4 Bedrooms12 Guests
10.0

Exceptional

11 reviews

$968
Average price / night
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NEW LUXURY PENTHOUSE CONDO
NEW LUXURY PENTHOUSE CONDO
Condo
Chicago, IL, 60622, United States
1.5k from Wood Street Gallery center

AC, Balcony, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms9 Guests
10.0

Exceptional

204 reviews

$603
Average price / night
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Large Chicago 3BR/3BA • Sleeps 7 • Near Downtown
Large Chicago 3BR/3BA • Sleeps 7 • Near Downtown
Condo
Chicago, IL, 60612, United States
1.5k from Wood Street Gallery center

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

3 Bedrooms7 Guests
10.0

Exceptional

34 reviews

$885
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 Wood Street Gallery.

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Frequently Asked Questions

You can explore 808 verified family-friendly vacation rentals in Wood Street Gallery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Wood Street Gallery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $187 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Wood Street Gallery 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 Wood Street Gallery 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 Wood Street Gallery often include amenities such as Child Friendly, Fireplace/Heating, and Internet. 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.