Vacation Rentals in Flat Iron Building, IL: Compare 10+ Sites & Save

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  6.  Flat Iron Building

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2349 Best Vacation Rentals in Flat Iron Building (Starting from $74)

Amazing Penthouse Skyline Views!
Amazing Penthouse Skyline Views!
House
Chicago, IL, USA
0.1k from Flat Iron Building 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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The Cornerstone - Designer 4BR Flat in Bucktown/WP
The Cornerstone - Designer 4BR Flat in Bucktown/WP
Apartment
Chicago, IL, 60622, United States
0.0k from Flat Iron Building center

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

4 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$978
Average price / night
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Designer Apt Billiards Private Patio 1 Parking
Designer Apt Billiards Private Patio 1 Parking
Apartment
Chicago, IL, USA
0.2k from Flat Iron Building center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$516
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
0.1k from Flat Iron Building 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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Modern Apt Billiards 1 Private Patio 1 Parking
Modern Apt Billiards 1 Private Patio 1 Parking
Apartment
Chicago, IL, USA
0.2k from Flat Iron Building center

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

3 Bedrooms10 Guests
8.0

Good

1 reviews

$449
Average price / night
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The Avery – Boutique Bucktown/WP Studio by Transit
The Avery – Boutique Bucktown/WP Studio by Transit
Apartment
Chicago, IL, 60622, United States
0.1k from Flat Iron Building center

AC, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, TV, Washer

New to Booking
$374
Average price / night
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Billiards Patio Parking
Billiards Patio Parking
Apartment
Chicago, IL, USA
0.2k from Flat Iron Building center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms10 Guests
New to Booking
$657
Average price / night
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1 Free Parking Sleeps 10
1 Free Parking Sleeps 10
Apartment
Chicago, IL, USA
0.2k from Flat Iron Building center

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

1 Bedroom10 Guests
New to Booking
$305
Average price / night
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FRONTDESK Spacious 2 BR Apt in Wicker Park
FRONTDESK Spacious 2 BR Apt in Wicker Park
Apartment
Chicago, IL, USA
0.5k from Flat Iron Building center

Balcony/Terrace, Internet, Air Conditioner

2 Bedrooms4 Guests
8.0

Good

1 reviews

$93
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 Flat Iron Building center

Apartments, Accommodations, Lodgings, Places to stay

4 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$434
Average price / night
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Trendy Wicker Park Loft with Parking
Trendy Wicker Park Loft with Parking
House
Chicago, IL, USA
0.7k from Flat Iron Building 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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4 Bedroom Penthouse Loft in Heart of Wicker Park
4 Bedroom Penthouse Loft in Heart of Wicker Park
House
Chicago, IL, 60622, United States
0.2k from Flat Iron Building center

AC, Dryer, Heater, Internet, Laundry, Washer

4 Bedrooms12 Guests
New to Booking
$717
Average price / night
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FRONTDESK Wicker Park 2 BR Apt with Courtyard
FRONTDESK Wicker Park 2 BR Apt with Courtyard
Apartment
Chicago, IL, USA
0.7k from Flat Iron Building center

Air Conditioner, Internet

2 Bedrooms4 Guests
6.8

Good

10 reviews

$74
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
0.2k from Flat Iron Building 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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The Twin Lions: Bespoke Travel Lodge w/Speakeasy*
The Twin Lions: Bespoke Travel Lodge w/Speakeasy*
Apartment
Chicago, IL, USA
0.7k from Flat Iron Building center

Entertainment, Fireplace/Heating, Air Conditioner, Pet Friendly, Laundry, Internet, Guest Services

3 Bedrooms6 Guests
9.0

Fabulous

17 reviews

$441
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
0.2k from Flat Iron Building 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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Bucktown Private Condo
Bucktown Private Condo
Apartment
Chicago, IL, USA
0.8k from Flat Iron Building center

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

2 Bedrooms4 Guests
9.5

Superb

23 reviews

$151
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
0.2k from Flat Iron Building 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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Wicker Park 2BR Modern Apartment DV3
Wicker Park 2BR Modern Apartment DV3
Apartment
Chicago, IL, USA
0.9k from Flat Iron Building center

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

2 Bedrooms5 Guests
9.0

Fabulous

18 reviews

$396
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
0.3k from Flat Iron Building 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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Spacious Bucktown Sanctuary
Spacious Bucktown Sanctuary
House
Chicago, IL, USA
0.9k from Flat Iron Building center

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

2 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$110
Average price / night
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Entire Condo and Parking at the heart of Wicker Park
Entire Condo and Parking at the heart of Wicker Park
Apartment
Chicago, IL, 60622, United States
0.3k from Flat Iron Building center

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

2 Bedrooms7 Guests
New to Booking
$309
Average price / night
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Bucktown Loft - top floor, near Bloomingdale Trail
Bucktown Loft - top floor, near Bloomingdale Trail
Apartment
Chicago, IL, 60622, United States
0.4k from Flat Iron Building center

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

1 Bedroom2 Guests
New to Booking
$181
Average price / night
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New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21
New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21
House
Chicago, IL, 60622, United States
0.4k from Flat Iron Building center

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

6 Bedrooms21 Guests
10.0

Exceptional

7 reviews

$2428
Average price / night
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Luxury Chicago 2 Story Condo: 10 Mins to Downtown
Luxury Chicago 2 Story Condo: 10 Mins to Downtown
Apartment
Chicago, IL, 60647, United States
0.4k from Flat Iron Building center

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

2 Bedrooms6 Guests
9.0

Fabulous

6 reviews

$401
Average price / night
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Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Apartment
Chicago, IL, 60622, United States
0.5k from Flat Iron Building center

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

2 Bedrooms6 Guests
9.2

Superb

9 reviews

$351
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
0.5k from Flat Iron Building center

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

3 Bedrooms8 Guests
New to Booking
$1027
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 Flat Iron Building.

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Frequently Asked Questions

You can explore 2349 verified vacation rentals in Flat Iron Building. 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 Flat Iron Building vary depending on the season, property size, and location. Rates typically start from around $74 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 Flat Iron Building 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 Flat Iron Building welcome pets. Currently, 24 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 Flat Iron Building often include amenities such as Fireplace/Heating, Internet, and Child Friendly. 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.