50 Best Chicago Apartments on Holiday Lettings - Lofts

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633 Vacation rentals

(23) Excellent 

41

Vacation apartment in Chicago

Illinois / Chicago

3 12 3 nights min

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children *2 options for the World Series: 3 bedroom 2 bath sleep 10 4 bedroom 4 bath sleep 8 - 16 Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Pa  …see more

from $446 / night

$2501 - $3900 / week

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from $446 / night

(9) Very Good 

7

Illinois / Chicago

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
  • Car not necessary
  • Air conditioning

 …see more

from $90 / night

$496 / week

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from $90 / night

(1) Excellent 

14

Vacation home in Chicago

Illinois / Chicago

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
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-Tile  …see more

from $170 / night

$1051 / week

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from $170 / night

(1) Excellent 

20

Chicago Vacation apartment rental

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • 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 $80 / night

$554 / week

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from $80 / night

(12) Very Good 

7

Illinois / Chicago

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $150 / night

$950 - $1021 / week

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from $150 / night

15

Vacation apartment in Chicago

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • 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 $68 / night

$476 / week

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from $68 / night

(1) Very Good 

14

Illinois / Chicago

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
  • Air conditioning

 …see more

from $120 / night

$840 / week

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from $120 / night

(1) Excellent 

19

Chicago Vacation apartment rental

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • 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 $110 / night

$764 / week

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from $110 / night

(4) Very Good 

8

Illinois / Chicago

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 11 mi
  • Child friendly
  • Car not necessary

 …see more

from $70 / night

$484 / week

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from $70 / night

(2)  

16

Illinois / Chicago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $80 / night

$501 - $1081 / week

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from $80 / night

(3) Excellent 

21

Vacation apartment in Chicago

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • 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 $90 / night

$624 / week

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from $90 / night

10

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Ask about children
  • Ask about pets

 …see more

from $97 / night

$677 / week

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from $97 / night

(5) Very Good 

11

Illinois / Chicago

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Ask about children
  • Air conditioning

 …see more

from $225 / night

$1251 / week

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from $225 / night

(42) Excellent 

57

Illinois / Chicago

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Car not necessary
  • Air conditioning
  • Ask about pets

 …see more

from $100 / night

$600 / week

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from $100 / night

24

Illinois / Chicago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly

 …see more

from $230 / night

$1375 - $2971 / week

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from $230 / night

13

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Ask about children
  • Ask about pets

 …see more

from $66 / night

$458 / week

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from $66 / night

16

Illinois / Chicago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Air conditioning

 …see more

from $200 / night

$1393 - $3213 / week

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from $200 / night

11

Illinois / Chicago

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from $299 / night

$2192 / week

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from $299 / night

20

Vacation apartment in Chicago

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Nearest beach 5 mi
  • 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 $90 / night

$624 / week

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from $90 / night

(1) Very Good 

25

Illinois / Chicago

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly

 …see more

from $250 / night

$1500 / week

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from $250 / night

38

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Ask about pets

 …see more

from $162 / night

$1131 / week

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from $162 / night

(3) Very Good 

9

Illinois / Chicago

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children

 …see more

from $105 / night

$501 / week

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from $105 / night

7

Illinois / Chicago

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $100 / night

$601 - $740 / week

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from $100 / night

(1) Very Good 

6

Illinois / Chicago

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden

 …see more

from $85 / night

$551 - $900 / week

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from $85 / night

(1)  

11

Illinois / Chicago

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $70 / night

$481 - $1081 / week

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from $70 / night

23

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $192 / night

$1338 / week

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from $192 / night

11

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from $197 / night

$1373 / week

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from $197 / night

(1) Very Good 

23

Illinois / Chicago

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary

 …see more

from $279 / night

$1559 - $3053 / week

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from $279 / night

(1) Excellent 

12

Illinois / Chicago

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $140 / night

$974 - $2513 / week

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from $140 / night

(4) Excellent 

32

Illinois / Chicago

1 4 14 nights min

  • 1 bedroom
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $120 / night

$1001 / week

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from $120 / night

(2) Excellent 

11

Illinois / Chicago

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $100 / night

$660 - $870 / week

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from $100 / night

(1) Excellent 

17

Illinois / Chicago

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning

 …see more

from $295 / night

$1751 / week

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from $295 / night

(1) Good 

9

Illinois / Chicago

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Air conditioning

 …see more

from $250 / night

$1201 / week

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from $250 / night

(3) Excellent 

21

Illinois / Chicago

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning

 …see more

from $351 / night

$2451 / week

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from $351 / night

(3) Excellent 

21

Illinois / Chicago

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly

 …see more

from $130 / night

$904 / week

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from $130 / night

(2) Very Good 

14

Illinois / Chicago

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $75 / night

$451 / week

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from $75 / night

(4) Excellent 

29

Illinois / Chicago

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $175 / night

$1400 - $2353 / week

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from $175 / night

(6) Very Good 

27

Illinois / Chicago

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly

 …see more

from $501 / night

$3501 / week

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from $501 / night

25

Illinois / Chicago

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Car not necessary

 …see more

from $125 / night

$1201 - $2251 / week

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from $125 / night

(2) Good 

34

Illinois / Chicago

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $80 / night

$551 - $840 / week

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from $80 / night