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Chicago holiday rentals

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  • Price: low to high
  • Distance: low to high

The Avondale Guesthouse

Excellent location
This property boasts excellent location. It has a score 9.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

127 reviews

9.4/10
Wi-Fi
Cycling
Paid shuttle service
Cots
Air conditioning
No pets allowed

The 6-room The Avondale Guesthouse Chicago villa offers swift access to various city sites, such as the Algonquin Park, situated nearly 5 minutes' walk away.

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Lincoln Park Living - 3 Queen Beds - Sleeps 6

Excellent location
This property boasts excellent location. It has a score 9.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

41 reviews

9/10
Wi-Fi
Air conditioning
No pets allowed

Situated nearly 25 minutes' walk from the baseball stadium "Wrigley Field", the 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6 Chicago villa invites guests to relax at a patio.

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Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

Superb location
This property boasts superb location. It has a score 8.7 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

42 reviews

9.6/10
Wi-Fi
Express check-in/ -out
Beach access
Tennis court
Cots
Air conditioning

Located 25 minutes' walk from the Welles Park, Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago offers movie nights for guests' leisure. The 2-bedroom holiday home features…

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Lincoln Park Living - Suite 1

Exceptional location
This property boasts exceptional location. It has a score 9.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

37 reviews

8.6/10
Wi-Fi
Free parking
Air conditioning
No pets allowed

The 2-bedroom Lincoln Park Living - Suite 1 Chicago villa offers quick access to such city attractions as Holy Covenant United Methodist Church, located only 6 minutes' walk away.

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Stunning Condo #2 - Downtown River North

Exceptional location
This property boasts exceptional location. It has a score 9.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

31 reviews

9.2/10
Wi-Fi
Air conditioning
No pets allowed

The 2-bedroom Stunning Condo #2 - Downtown River North Chicago villa is situated just 6 minutes' walk from the long-standing Carl Hammer Gallery, featuring such comforts as Wi-Fi and a car park.

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The Black And White Suite

Superb location
This property boasts superb location. It has a score 8 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Good

20 reviews

7/10
Wi-Fi
Free parking
Air conditioning
Pets allowed

Located 2.6 km from the Lakefront Trail, The Black And White Suite Chicago villa gives access to various tourist sites in the vicinity.

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Suite 2 On Southport 4 Queen Beds

Excellent location
This property boasts excellent location. It has a score 9.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms

Situated around 500 metres from Saint Josaphat Catholic Church, Suite 2 On Southport 4 Queen Beds Chicago villa offers easy access to numerous tourist spots in the area.

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Lincoln Park Living - Suite 2

Exceptional location
This property boasts exceptional location. It has a score 9.7 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

20 reviews

8.8/10
Wi-Fi
Air conditioning
No pets allowed

The 2-bedroom Lincoln Park Living - Suite 2 Chicago villa offers easy access to such tourist spots as Holy Covenant United Methodist Church, located a mere 450 metres away.

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Stunning Duplex Condo #1 - Downtown River North

Excellent location
This property boasts excellent location. It has a score 9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

26 reviews

9.2/10
Wi-Fi
Air conditioning
No pets allowed

Located around 25 minutes on foot from the North Avenue Beach, the 3-bedroom Stunning Duplex Condo #1 - Downtown River North Chicago villa offers a patio with views of the city. Offering Wi-Fi, the…

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Spacious 5-Br House Near Transit W Parking

Excellent location
This property boasts excellent location. It has a score 9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

18 reviews

8.6/10
Wi-Fi
Express check-in/ -out
Air conditioning
Pets allowed

Situated within a 10-minute drive of the 184-acre Garfield Park Conservatory, the 3-bedroom Spacious 5-Br House Near Transit W Parking Chicago villa entices guests to explore various tourist…

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Spacious Row Home Next Transit Near Downtown W Parking

Excellent location
This property boasts excellent location. It has a score 9.2 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

19 reviews

9.6/10
Wi-Fi
Air conditioning
Pets allowed

The 3-bedroom Spacious Row Home Next Transit Near Downtown W Parking Chicago offers swift access to various city sites, such as 345 Art Gallery, situated nearly 5 minutes' walk away.

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Romantic 3 Bed Home In The Heart Of The Park

Excellent location
This property boasts excellent location. It has a score 9.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms

Romantic 3 Bed Home In The Heart Of The Park Chicago provides easy access to various city attractions, such as Greater Metropolitan MB Church, situated 6 minutes' walk away.

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Magnificent New Home W/8 Beds & Free Parking

Superb location
This property boasts superb location. It has a score 8.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

15 reviews

9.4/10
Wi-Fi
Air conditioning
No pets allowed

Located around 5 minutes' walk from the live music venue "Congress Theater", the 3-bedroom Magnificent New Home W/8 Beds & Free Parking Chicago offers quick access to various city attractions in the…

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Historic Luxury Townhouse In Downtown Chicago

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

12 reviews

9.8/10
Free Wi-Fi in public areas
Cots
Air conditioning
Pets allowed

Offering garden views, the 3-bedroom Historic Luxury Townhouse In Downtown Chicago Villa is situated a mere 6 minutes' walk from the skyscraper 360 Chicago Observation Deck.

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Breathtaking Downtown Penthouse B - Sleeps 11

Excellent location
This property boasts excellent location. It has a score 9.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

15 reviews

9.6/10
Wi-Fi
Air conditioning
No pets allowed

The 3-bedroom Breathtaking Downtown Penthouse B - Sleeps 11 Villa Chicago is situated only 6 minutes' walk from the long-standing Carl Hammer Gallery, featuring such comforts as Wi-Fi and a car park.…

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Beautifully Renovated House 10 Mins From Downtown

Excellent location
This property boasts excellent location. It has a score 9.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

12 reviews

8.2/10
Wi-Fi
Express check-in/ -out
Beach access
Water slides
Baby pushchair
Air conditioning

Located a 10-minute drive from the Guaranteed Rate Field, Beautifully Renovated House 10 Mins From Downtown Villa Chicago offers karaoke for guests' leisure. Offering complimentary private parking as…

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Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

Exceptional location
This property boasts exceptional location. It has a score 9.9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

8 reviews

9.4/10
Wi-Fi
Jacuzzi
Children's play area
Air conditioning
No pets allowed

Situated merely a 9-minute walk from Korean Bethel Presbyterian Church Of Chicago, the 2-bedroom Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub Chicago invites guests…

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Beautiful Remodeled Penthouse Unit In Old Town

Superb location
This property boasts superb location. It has a score 8.6 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

12 reviews

8.8/10
Wi-Fi
Air conditioning
No pets allowed

The 2-bedroom Beautiful Remodeled Penthouse Unit In Old Town Villa Chicago offers swift access to various city sites, such as Zanies, situated nearly 5 minutes' walk away.

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The Village Inn By Dakota Gal Digs

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

3 reviews

10/10
Free Wi-Fi in rooms
Air conditioning
Pets allowed

The Village Inn By Dakota Gal Digs Chicago villa is located a 10-minute drive from the baseball stadium "Wrigley Field" and invites guests to enjoy a patio.

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Wi-Fi

Located just an 11-minute walk from the baseball stadium "Wrigley Field", Modern Wrigley Oasis With Parking! Villa Chicago provides access to various tourist attractions in the vicinity.

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The Logandale: Huge Mid-Century Home, Sleeps 15

Exceptional location
This property boasts exceptional location. It has a score 9.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi

The Logandale: Huge Mid-Century Home, Sleeps 15 Chicago offers quick access to such city attractions as the Saint Hyacinth Roman Catholic Church, located about a 5-minute walk away.

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Located 7 km from the Sprawling hands-on Museum of Science and Industry, Cozy 4Bd House Fireplace And Pond Chicago villa gives access to various tourist sites in the vicinity.

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Chicago Home Near Navy Pier And Shedd Aquarium!

Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms

Situated only 1.8 km from Nat King Cole Park, Chicago Home Near Navy Pier And Shedd Aquarium! entices guests to explore various tourist attractions in the area.

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Boutique Garden House Chicago 3-Story Sleeps 12

Excellent location
This property boasts excellent location. It has a score 9.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

6 reviews

9.6/10
Wi-Fi
Free parking
Air conditioning
No pets allowed

Staying at the 3-bedroom Boutique Garden House Chicago 3-Story Sleeps 12 Villa, guests can visit Saint Columbanus Church, which is a mere 7 minutes' walk away.

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5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

Superb location
This property boasts superb location. It has a score 8.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

3 reviews

8.2/10
Wi-Fi
Express check-in/ -out
Beach access
Tennis court
Business centre
Cots

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa is nestled around a 20-minute walk from Lake Michigan and invites guests to unvind on a terrace. The 4-bedroom holiday…

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Stunning 5Br Home In Heart Of Chicago With 2 Rooftops

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

10/10
Wi-Fi
Free parking
Game room
Air conditioning
No pets allowed

Located within a 6-km distance of the skyscraper 360 Chicago Observation Deck, the 4-bedroom Stunning 5Br Home In Heart Of Chicago With 2 Rooftops offers a patio with views of the city. Offering Wi…

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Chicago Treasure 4 Bed Getaway

Excellent location
This property boasts excellent location. It has a score 9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms

Located a 10-minute ride from the skyscraper 360 Chicago Observation Deck, Chicago Treasure 4 Bed Getaway Villa provides access to various tourist attractions in the vicinity.

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Wi-Fi

Staying at Logan Square Oasis Villa Chicago, guests can easily reach Half Italian, located just 0.6 km away.

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Free Wi-Fi
Air conditioning
Pets allowed

Situated 2.9 km from the large Norridge Park District, Charming Home In Portage Park Chicago provides access to numerous tourist attractions in the area.

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River North Hideaway With Amazing Views And Parking

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi

Located around 5 minutes on foot from the Holy Name Cathedral, River North Hideaway With Amazing Views And Parking Villa Chicago offers quick access to various city attractions in the vicinity.

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Wi-Fi in rooms

Nestled a 9-minute walk from the Buffalo Exchange, Chicago New 2Br Home W 3 Beds And Highspeed Internet entices guests to explore various tourist destinations nearby.

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Perfect Location Across From Park & Train Station

Superb location
This property boasts superb location. It has a score 8.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

8 reviews

9.6/10
Wi-Fi
Free parking
Air conditioning
Pets allowed

Situated 6 minutes' walk from Midwest Athletic Club, Perfect Location Across From Park & Train Station Villa Chicago entices guests with views of the garden.

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Roscoe Village Family Hideaway

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

1 review

9/10
Wi-Fi
Free parking
Air conditioning
No pets allowed

The 3-bedroom Roscoe Village Family Hideaway Chicago villa offers quick access to such city attractions as Loba Pastry + Coffee, located nearly a 5-minute walk away. Situated in the Roscoe Village…

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Modern 3Br Near Mccormick & South Loop

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

1 review

10/10
Wi-Fi in rooms
Fitness centre
Cycling
Wheelchair access
Air conditioning
Pets allowed

Offering a patio overlooking the city, Modern 3Br Near Mccormick & South Loop Villa Chicago is located just a 6-minute walk from Trinity Episcopal Church. Guests can enjoy cycling at this property…

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Stylish 3Br Gem In Prime Location

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

10/10
Wi-Fi in rooms
Fitness centre
Cycling
Game room
Wheelchair access
Air conditioning

Stylish 3Br Gem In Prime Location Villa Chicago is located 3.1 km from the third-smallest stadium "Soldier Field" and provides cycling for active guests.

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Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

Exceptional location
This property boasts exceptional location. It has a score 9.9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

26 reviews

9.6/10
Wi-Fi
Express check-in/ -out
Beach access
Golf course
Business centre
Cots

The 3-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa offers quick access to such city attractions as The Noble Horse Theatre, located about a 5-minute walk…

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Gorgeous 5 Bedroom Gem With Games

Superb location
This property boasts superb location. It has a score 8.7 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

10/10
Wi-Fi
Fitness centre
Billiard tables
Game room
Air conditioning
Pets allowed

The 2-bedroom Gorgeous 5 Bedroom Gem With Games Chicago villa offers easy access to such tourist spots as Saint Sabina Roman Catholic Church, located a mere 6 minutes' walk away. Guests can enjoy…

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2 Newly Built Luxury Condos With Private Roofdeck

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

1 review

9/10
Wi-Fi
Air conditioning
No pets allowed

Situated within a 2-km distance of the Skydeck Chicago, the 6-bedroom 2 Newly Built Luxury Condos With Private Roofdeck Chicago villa features a patio with views of the city. Offering Wi-Fi, the…

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Personal Gym Luxury Balcony Condo

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

10/10
Wi-Fi
24-hour reception
Air conditioning
Pets allowed

Offering a location 2.7 km from the Museum of Hummels, the 1-bedroom Personal Gym Luxury Balcony Condo Chicago villa gives access to various tourist spots in the area.

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New Modern 3Br, Gym, Workspace, Quiet Location

Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

3 reviews

9.2/10
Wi-Fi
24-hour reception
Fitness centre
Jacuzzi
Air conditioning
Pets allowed

Offering a Jacuzzi, the 2-bedroom New Modern 3Br, Gym, Workspace, Quiet Location Chicago villa is located around a 25-minute walk from the large Norridge Park District.

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5Br 5Ba Architectural Estate-Theatre Gym Rooftop

Superb location
This property boasts superb location. It has a score 8.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

3 reviews

8.6/10
Wi-Fi
Fitness centre
Golf course
Game room
Air conditioning
No pets allowed

Offering a sauna for a relaxing experience, 5Br 5Ba Architectural Estate-Theatre Gym Rooftop Chicago villa is located 7 km from the Oak Magnificent Mile Street.

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2 Mi To South Shore Beach Urban Retreat With Yard

Superb location
This property boasts superb location. It has a score 8.7 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

9.4/10
Wi-Fi
No pets allowed

2 Mi To South Shore Beach Urban Retreat With Yard Chicago villa offers swift access to various city sites, such as South Shore Bible Baptist Church, situated a mere 6 minutes' walk away.

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Woodlawn Oasis

Very good location
This property boasts very good location. It has a score 7.8 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

9 reviews

8.8/10
Wi-Fi
Free parking
Cots
Air conditioning
No pets allowed

Staying at the 3-bedroom Woodlawn Oasis Villa Chicago, guests can easily reach the Sprawling hands-on Museum of Science and Industry, located 2.8 km away.

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Newly Updated Vintage 6 Bedroom Single Family Home Home

Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

1 review

9/10
Wi-Fi
Free parking
Air conditioning
No pets allowed

Nestled 6 km from the Art Institute of Chicago, Newly Updated Vintage 6 Bedroom Single Family Home Home Chicago entices guests to explore various tourist destinations nearby.

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Near Lake & Museum • Modern • Game Area

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

10/10
Wi-Fi
24-hour reception
Beach access
Aqua park
Cots
Air conditioning

Nestled within 500 metres of New Spiritual Light M.B. Church, Near Lake & Museum • Modern • Game Area Chicago villa entices guests to explore various tourist destinations nearby.

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Stylish Chicago Retreat Walk To Loyola University

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

9.4/10
Wi-Fi
Beach access
Cots
Pets allowed

The 4-bedroom Stylish Chicago Retreat Walk To Loyola University villa provides easy access to various city attractions, such as Mundelein College, situated nearly a 5-minute walk away.

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Victorian Mansion In Garfield Park

Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

2 reviews

9.4/10
Wi-Fi
No pets allowed

Situated just a 6-minute walk from Chicago Community Mennonite Church, the 1-bedroom Victorian Mansion In Garfield Park Villa Chicago entices guests with views of the garden.

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Envitae Hotel 4Br Luxury Modern Apartments

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

1 review

10/10
Wi-Fi
Express check-in/ -out
Fitness centre
Aqua park
Cots
Air conditioning

The 6-room Envitae Hotel 4Br Luxury Modern Apartments Chicago villa offers quick access to such city attractions as the PRYSM Nightclub, located approximately 5 minutes' walk away.

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Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

3 reviews

9.6/10
Wi-Fi
Free parking
Express check-in/ -out
Darts
Cots
Air conditioning

The 3-bedroom Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla Chicago offers quick access to such city attractions as Santa Maria Addolorata Parish, located…

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4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!

Excellent

4 reviews

9.4/10
Wi-Fi
Express check-in/ -out
Beach access
Fitness centre
Tennis court
Spa lounge

The 4-bedroom 4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome Chicago is situated about 5 minutes' walk from Eva's Cafe, featuring such comforts as Wi-Fi and complimentary…

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