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

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655 Holiday homes

(23) Excellent 

41

Holiday apartment in Chicago

Illinois / Chicago

3 12 3 nights min

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
“Amazing Chicago Loft!” Carole & Basil's place is great! My group of 7 very much enjoyed our stay, and all agreed would gladly stay again. There is plenty of room for a large group- amazing kitchen complete with many amenities, spacious bedrooms and ba  …see more

from £354 / night

£1985 - £3096 / week

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from £354 / night

(9) Very Good 

7

Illinois / Chicago

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning

 …see more

from £71 / night

£393 / week

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from £71 / 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 £79 / night

£476 / week

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from £79 / night

(1) Excellent 

14

Holiday 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 £135 / night

£834 / week

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from £135 / 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 £182 / night

£1091 - £2358 / week

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from £182 / night

(1) Excellent 

20

Chicago holiday apartment rental

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
This central loop location will allow you to walk to work and the top amenities will allow you to relax after work. Treat yourself to a luxury upgrade from a hotel.  …see more

from £63 / night

£439 / week

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from £63 / night

(4) Very Good 

8

Illinois / Chicago

2 8 1 night min

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

 …see more

from £55 / night

£384 / week

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from £55 / night

(1) Excellent 

19

Chicago holiday apartment rental

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
This central loop location will allow you to walk to work and the top amenities will allow you to relax after work. Treat yourself to a luxury upgrade from a hotel.  …see more

from £87 / night

£606 / week

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from £87 / night

13

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £52 / night

£363 / week

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from £52 / 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 £96 / night

£667 / week

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from £96 / night

38

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £129 / night

£898 / week

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from £129 / night

15

Holiday apartment in Chicago

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
This top West Loop location will allow you to walk to work, enjoy stunning views from home, and have the luxury of restaurants, nightlife, museums and shopping at your doorstep.  …see more

from £54 / night

£378 / week

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from £54 / 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 £120 / night

£754 - £810 / week

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from £120 / night

(3) Excellent 

21

Holiday apartment in Chicago

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This central loop location will allow you to walk to work and the top amenities will allow you to relax after work. Treat yourself to a luxury upgrade from a hotel.  …see more

from £71 / night

£495 / week

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from £71 / night

(5) Very Good 

11

Illinois / Chicago

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £179 / night

£993 / week

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from £179 / night

(3) Excellent 

10

Illinois / Chicago

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £182 / night

£1273 - £1717 / week

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from £182 / night

(3) Very Good 

9

Illinois / Chicago

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask owner if suitable for children

 …see more

from £84 / night

£397 / week

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from £84 / night

26

Illinois / Chicago

2 4 127 nights min

  • 2 bedrooms
  • Sleeps 4
  • 127 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £151 / night

£1055 / week

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from £151 / 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 £64 / night

£397 - £858 / week

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from £64 / night

(2) Average 

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 £64 / night

£437 - £667 / week

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from £64 / night

7

Illinois / Chicago

2 4 Min stay varies

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

 …see more

from £79 / night

£477 - £588 / week

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from £79 / night

(1) Very Good 

19

Illinois / Chicago

3 6 Min stay varies

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

 …see more

from £222 / night

£1238 - £2423 / week

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from £222 / night

10

Illinois / Chicago

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £77 / night

£538 / week

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from £77 / night

20

Holiday apartment in Chicago

Illinois / Chicago

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Nearest beach 5 km
  • Child friendly
  • Car not necessary
This top West Loop location will allow you to walk to work, enjoy stunning views from home, and have the luxury of restaurants, nightlife, museums and shopping at your doorstep.  …see more

from £71 / night

£495 / week

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from £71 / 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 £56 / night

£381 - £858 / week

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from £56 / 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 £278 / night

£1945 / week

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from £278 / night

(4) Excellent 

32

Illinois / Chicago

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 4 km
  • Child friendly
  • Car not necessary

 …see more

from £267 / night

£1493 - £2333 / week

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from £267 / night

(1) Very Good 

25

Illinois / Chicago

2 7 1 night min

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

 …see more

from £199 / night

£1191 / week

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from £199 / 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 £238 / night

£1740 / week

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from £238 / 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 £60 / night

£358 / week

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from £60 / night

(6) Very Good 

27

Illinois / Chicago

2 6 2 nights min

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

 …see more

from £397 / night

£2778 / week

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from £397 / night

(3) Excellent 

21

Illinois / Chicago

2 5 Min stay varies

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

 …see more

from £103 / night

£717 / week

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from £103 / night

(2) Average 

7

Illinois / Chicago

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Nearest beach 11 km
  • Child friendly
  • Air conditioning

 …see more

from £47 / night

£328 / week

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from £47 / 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 £152 / night

£1062 / week

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from £152 / night

(1) Excellent 

14

Illinois / Chicago

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £95 / night

£662 - £1662 / week

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from £95 / night

(1) Average 

9

Illinois / Chicago

2 6 3 nights min

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

 …see more

from £199 / night

£953 / week

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from £199 / night

(3) Average 

6

Illinois / Chicago

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning

 …see more

from £96 / night

£596 / week

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from £96 / night

15

Illinois / Chicago

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning

 …see more

from £96 / night

£675 - £786 / week

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from £96 / night

13

Illinois / Chicago

4 8 3 nights min

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

 …see more

from £219 / night

£1528 / week

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from £219 / night

(2)  

28

Illinois / Chicago

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Ask owner if suitable for children
  • Car not necessary
  • Ask about pets

 …see more

from £278 / night

£1588 / week

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from £278 / night

Top Destination reviews

Beautiful 2 bed room apartment
first stop on a 3 week tour and did not disappoint

quite a bit outside town, but once we got the hang of the transport it was ok. stairs to the front of house where a bit hard work for my elderly parents, but once inside the accommodation was great. … see more