Chicago holiday rentals

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2025-09-13
2025-09-14

Maximum period that can be booked is 30 days. Please enter alternative dates.

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2025-09-13
2025-09-14

Maximum period that can be booked is 30 days. Please enter alternative dates.

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Lowest price
City centre
5-star hotels
Highest rating
Free Wi-Fi
9.4
Excellent
The Avondale Guesthouse
The Avondale Guesthouse

The Avondale Guesthouse

Excellent
135 reviews
9.4
2973 North Elston Avenue, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9.1 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Free Wi-Fi
Cycling
Paid shuttle service
Cots
Air conditioning
No pets allowed
Located 400 metres from Riverview Park, The Avondale Guesthouse offers a terrace with a view over the street. This 6-room villa features opportunities for cycling in the area, at a medium distance…
9.6
Excellent
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

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

Excellent
42 reviews
9.6
2713 West Balmoral Avenue, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Beach access
Tennis court
Cycling
Darts
Badminton
Cots
Children's play area
Game room
Air conditioning
The 2-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa boasts a location merely a 6-minute walk from North Shore 7th Day Adventist Church and offers guests to enjoy live performances…
Lincoln Park Living - Suite 1
Lincoln Park Living - Suite 1

Lincoln Park Living - Suite 1

West Diversey Parkway, Chicago, United States
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 only 0.8 km from Saint George Greek Orthodox Church, Lincoln Park Living - Suite 1 invites guests to relax at a sunny patio.
Stunning Condo #2 - Downtown River North
Stunning Condo #2 - Downtown River North

Stunning Condo #2 - Downtown River North

811 N Sedgwick St, Chicago, United States
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
The 2-bedroom Stunning Condo #2 - Downtown River North is situated a 6-minute walk from St. Joseph Parish, featuring such comforts as Wi-Fi and a car park.
Lincoln Park Living - 3 Queen Beds - Sleeps 6
Lincoln Park Living - 3 Queen Beds - Sleeps 6

Lincoln Park Living - 3 Queen Beds - Sleeps 6

1147 West Diversey Parkway, Chicago, United States
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 in rooms
Along with Wi-Fi and parking, the 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6 offers proximity to Willis Tower, located a 15-minute ride away.
The Black And White Suite
The Black And White Suite

The Black And White Suite

611 East 41St Street, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.4 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
Pets allowed
Located approximately 7 km from Skydeck Chicago, 4-bedroom The Black And White Suite provides access to various tourist attractions in the vicinity.
Romantic 3 Bed Home In The Heart Of The Park
Romantic 3 Bed Home In The Heart Of The Park

Romantic 3 Bed Home In The Heart Of The Park

5923 South Indiana Avenue, Chicago, United States
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
Wi-Fi
2-bedroom Romantic 3 Bed Home In The Heart Of The Park offers quick access to such tourist spots as Greater Metropolitan MB Church, situated around 500 metres away.
Suite 2 On Southport 4 Queen Beds
Suite 2 On Southport 4 Queen Beds

Suite 2 On Southport 4 Queen Beds

2501 North Southport Avenue, Chicago, United States
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
The 2-bedroom Suite 2 On Southport 4 Queen Beds offers quick access to such city attractions as Rotofugi Gallery, located merely a 5-minute walk away.
9.2
Excellent
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

Excellent
29 reviews
9.2
329 West Schiller Street Back, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 9.8 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Beach access
Golf course
Hiking
Business centre
Cots
Located merely a 5-minute stroll from Eva's Cafe, Couture Themed 3 Bedroom In Prime Spot With Patio, Parking, Fireplace, Pets Welcome offers a terrace with a view over the garden. The 3-bedroom villa…
9.2
Excellent
Spacious Row Home Next Transit Near Downtown W Parking
Spacious Row Home Next Transit Near Downtown W Parking

Spacious Row Home Next Transit Near Downtown W Parking

Excellent
15 reviews
9.2
3133 West Fulton Street, Chicago, United States
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!
Free Wi-Fi
Air conditioning
Pets allowed
Situated a 5-minute walk from 345 Art Gallery, Spacious Row Home Next Transit Near Downtown W Parking entices guests with views of the garden.
Lincoln Park Living - Suite 2
Lincoln Park Living - Suite 2

Lincoln Park Living - Suite 2

1147 West Diversey Parkway, Chicago, United States
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!
Wi-Fi in rooms
The 2-bedroom Lincoln Park Living - Suite 2 offers quick access to such city attractions as Rotofugi Gallery, located about a 5-minute walk away.
Chic Green L Near Downtown & Il Medical District
Chic Green L Near Downtown & Il Medical District

Chic Green L Near Downtown & Il Medical District

602 South Western Avenue, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.8 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi
Pets allowed
Staying at the 1-bedroom Chic Green L Near Downtown & Il Medical District, guests can easily reach Cloud Gate, located about 6 km away.
Chicago Home With Spacious Yard 14 Mi To Dtwn
Chicago Home With Spacious Yard 14 Mi To Dtwn

Chicago Home With Spacious Yard 14 Mi To Dtwn

Chicago, United States
Superb location
This property boasts superb location. It has a score 8.1 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
The 2-bedroom Chicago Home With Spacious Yard 14 Mi To Dtwn is located 12 minutes' walk from A. Philip Randolph Pullman Porter Museum, giving access to various tourist spots nearby.
Luxe 4Br With Hot Tub & Game Room
Luxe 4Br With Hot Tub & Game Room

Luxe 4Br With Hot Tub & Game Room

1654 West Ohio Street, Chicago, United States
Wi-Fi in rooms
Cots
Positioned 2.9 km from bustling shopping destinations such as The Merchandise Mart Mall, Luxe 4Br With Hot Tub & Game Room offers guests to use parking.
Breathtaking Downtown Penthouse A - Sleeps 11
Breathtaking Downtown Penthouse A - Sleeps 11

Breathtaking Downtown Penthouse A - Sleeps 11

811 N Sedgwick St, Chicago, United States
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!
Wi-Fi in rooms
Wi-Fi
The 3-bedroom Breathtaking Downtown Penthouse A - Sleeps 11 Villa is situated just 400 metres from Holy Family Lutheran Church, featuring such comforts as Wi-Fi and a car park.
9
Excellent
Magnificent New Home W/8 Beds & Free Parking
Magnificent New Home W/8 Beds & Free Parking

Magnificent New Home W/8 Beds & Free Parking

Excellent
8 reviews
9
2019 North Bingham Street, Chicago, United States
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!
Free Wi-Fi
Air conditioning
No pets allowed
The 3-bedroom Magnificent New Home W/8 Beds & Free Parking offers swift access to various city sites, such as the live music venue "Congress Theater", situated 5 minutes' walk away.
Beautifully Remodeled Flat Downtown #3N
Beautifully Remodeled Flat Downtown #3N

Beautifully Remodeled Flat Downtown #3N

858 North Orleans Street #3N, Chicago, United States
Pleasant location
This property boasts pleasant location. It has a score 6.7 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Wi-Fi
Beautifully Remodeled Flat Downtown #3N Villa offers quick access to such city attractions as Saint Luke Church of God in Christ, located about a 5-minute walk away.
5 Mi To Millennium Park Apartment With Fireplaces
5 Mi To Millennium Park Apartment With Fireplaces

5 Mi To Millennium Park Apartment With Fireplaces

3461 W Adams St, Chicago, United States
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 in rooms
Located around 7 km from Skydeck Chicago, the 1-bedroom Griffin Mansion With Yard, 5 Mi To Dtwn Chicago! Villa offers a sunny patio with views of the garden. Offering Wi-Fi, the accommodation is just…
Beautiful Remodeled Penthouse Unit In Old Town
Beautiful Remodeled Penthouse Unit In Old Town

Beautiful Remodeled Penthouse Unit In Old Town

1556 North La Salle Street, Chicago, United States
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!
Wi-Fi in rooms
Beautiful Remodeled Penthouse Unit In Old Town Villa provides easy access to various city attractions, such as Couch Tomb, situated only 6 minutes' walk away.
10
Excellent
The Logandale: Huge Mid-Century Home, Sleeps 15
The Logandale: Huge Mid-Century Home, Sleeps 15

The Logandale: Huge Mid-Century Home, Sleeps 15

Excellent
5 reviews
10
2920 North Gresham Avenue, Chicago, United States
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!
Free Wi-Fi
Children's play area
Game room
Air conditioning
No pets allowed
The Logandale: Huge Mid-Century Home, Sleeps 15 is situated around 5 minutes on foot from Saint Wenceslaus Roman Catholic Church, featuring such comforts as Wi-Fi and parking.

All hotels in Chicago are booked for your dates. Try other dates

2025-09-13
2025-09-14

Maximum period that can be booked is 30 days. Please enter alternative dates.

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