Apartments in Chicago and houses – Holiday Lettings - Holiday Rentals Chicago

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790 Holiday homes

(22) Excellent 

1 / 41

Magic Factory Loft 3BD 2 BA - Chicago apartment sleeps 10

Illinois / Chicago

3 10 3 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Child friendly ; Car not necessary; Air conditioning;
Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago. If you’re heading to Chicago and l  …see more

from £300 / night

£1894 - £2425 / week

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from £300 / night

(1) Excellent 

1 / 14

MODERN 3BD 2BTH BRICK-STYLE RANCH! - Chicago house sleeps 10

Illinois / Chicago

3 10 3 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!!ASK ABOUT OUR PRICE MATCHING OPTION!!Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people.-3 Bedrooms-2 Bathroom-Hardwood Floors-Tiled Bathroom-Centrally controlled Heat and Air-Big  …see more

from £129 / night

£796 / week

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from £129 / night

1 / 15

Presidential Towers Studio - Chicago apartment sleeps 2

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Child friendly ; Car not necessary; Air conditioning;
Choose from Studio, Jr. One Bedroom or One Bedroom Apartments. The property is between Chicago's business district, theater district or West Loop restaurant district. Check out live shows at the Bank of America Theatre (1,950 feet) before catching a train at Ogilvie St  …see more

from £60 / night

£419 / week

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from £60 / night

(1) Excellent 

1 / 19

Chicago Loop Luxury One Bedroom - Chicago apartment sleeps 4

Illinois / Chicago

1 4 30 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 30 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Swimming pool;
Choose from Studio, Jr. One Bedroom, One Bedroom and upgraded One Bedroom + Den apartments. An on-site pool highlights this modern apartment in Chicago's theatre district. The property is 1,650 feet from iconic Willis Tower and just 10 minutes' walk from Millennium Par  …see more

from £91 / night

£632 / week

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from £91 / night

(2) Excellent 

1 / 21

Chicago Loop Luxury Jr. One Bedroom - Chicago apartment sleeps 4

Illinois / Chicago

1 4 30 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 30 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Choose from Studio, Jr. One Bedroom, One Bedroom and upgraded One Bedroom + Den apartments. An on-site pool highlights this modern apartment in Chicago's theatre district. The property is 1,650 feet from iconic Willis Tower and just 10 minutes' walk from Millennium Par  …see more

from £75 / night

£525 / week

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from £75 / night

(1) Excellent 

1 / 20

Chicago Loop Luxury Studio Apartment - Chicago apartment sleeps 4

Illinois / Chicago

1 4 30 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 30 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Swimming pool;
Choose from Studio, Jr. One Bedroom, One Bedroom and upgraded One Bedroom + Den apartments. An on-site pool highlights this modern apartment in Chicago's theatre district. The property is 1,650 feet from iconic Willis Tower and just 10 minutes' walk from Millennium Par  …see more

from £68 / night

£472 / week

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from £68 / night

1 / 20

Presidential Towers One Bedroom - Chicago apartment sleeps 4

Illinois / Chicago

1 4 30 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 30 nights min stay
Key info: Nearest beach 5 km; Child friendly ; Car not necessary;
Choose from Studio, Jr. One Bedroom or One Bedroom Apartments. The property is between Chicago's business district, theater district or West Loop restaurant district. Check out live shows at the Bank of America Theatre (1,950 feet) before catching a train at Ogilvie St  …see more

from £83 / night

£579 / week

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from £83 / night

1 / 30

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £102 / night

£708 / week

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from £102 / night

1 / 37

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Ask owner if suitable for children; Ask about pets;
 …see more

from £114 / night

£796 / week

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from £114 / night

(3) Excellent 

1 / 7

Illinois / Chicago

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Ask owner if suitable for children; Car not necessary; Air conditioning;
 …see more

from £68 / night

£375 / week

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from £68 / night

1 / 6

Illinois / Chicago

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £190 / night

£1326 / week

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from £190 / night

1 / 7

Illinois / Chicago

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £133 / night

£929 / week

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from £133 / night

1 / 15

Illinois / Chicago

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
 …see more

from £53 / night

£366 / week

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from £53 / night

1 / 8

Illinois / Chicago

3 5 2 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £152 / night

£1061 / week

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from £152 / night

1 / 17

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £153 / night

£1066 / week

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from £153 / night

1 / 8

Illinois / Chicago

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £379 / night

£2652 / week

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from £379 / night

1 / 5

Illinois / Chicago

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £91 / night

£637 / week

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from £91 / night

1 / 10

Illinois / Chicago

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £152 / night

£1137 / week

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from £152 / night

(7) Very Good 

1 / 7

Illinois / Chicago

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
 …see more

from £114 / night

£720 - £773 / week

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from £114 / night

1 / 30

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £96 / night

£672 / week

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from £96 / night

1 / 30

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £107 / night

£743 / week

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from £107 / night

(18) Very Good 

1 / 39

Illinois / Chicago

2 1 night min stay

  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 8 km; Ask owner if suitable for children; Car not necessary;
 …see more

from £60 / night

£345 / week

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from £60 / night

(35) Very Good 

1 / 57

Illinois / Chicago

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Not suitable for children; Car not necessary; Air conditioning;
 …see more

from £75 / night

£454 / week

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from £75 / night

1 / 21

Illinois / Chicago

Studio 2 30 nights min stay

  • Studio
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £85 / night

£593 / week

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from £85 / night

1 / 12

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
 …see more

from £132 / night

£918 / week

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from £132 / night

1 / 6

Illinois / Chicago

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £238 / night

£1660 / week

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from £238 / night

1 / 9

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £141 / night

£982 / week

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from £141 / night

1 / 7

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
 …see more

from £128 / night

£891 / week

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from £128 / night

1 / 16

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £100 / night

£699 / week

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from £100 / night

1 / 23

Illinois / Chicago

Studio 2 30 nights min stay

  • Studio
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £81 / night

£566 / week

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from £81 / night

1 / 39

Illinois / Chicago

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Suitable for children age 5+; No pets allowed;
 …see more

from £46 / night

£273 - £857 / week

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from £46 / night

1 / 3

Illinois / Chicago

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £106 / night

£663 / week

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from £106 / night

1 / 23

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £145 / night

£1013 / week

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from £145 / night

1 / 10

Illinois / Chicago

2 4 30 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £206 / night

£1438 / week

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from £206 / night

1 / 40

Illinois / Chicago

1 4 30 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 30 nights min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £171 / night

£1364 / week

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from £171 / night

(2) Very Good 

1 / 9

Illinois / Chicago

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Ask owner if suitable for children; No pets allowed;
 …see more

from £80 / night

£379 / week

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from £80 / night

1 / 20

Illinois / Chicago

1 4 4 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Child friendly ; Car not necessary; Air conditioning;
 …see more

from £304 / night

£2122 / week

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from £304 / night

1 / 22

Illinois / Chicago

Studio 2 30 nights min stay

  • Studio
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £81 / night

£566 / week

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from £81 / night

1 / 14

Illinois / Chicago

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £57 / night

£398 / week

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from £57 / night

1 / 10

Illinois / Chicago

1 2 30 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 30 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £151 / night

£1056 / week

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from £151 / night

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