Chicago apartments, Houses and holiday rentals

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229 Holiday homes

Travellers going to Chicago are booking May dates now. Secure your holiday home today and have the perfect trip.

(6) Very Good 

1 / 27

Holiday apartment in Chicago

Illinois / Chicago

2 6 1 night min stay

Apartment / 2 bedrooms / sleeps 6 / 1 night min stay

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from £244 / night

£1389 - £1997 / week

Book

from £244 / night

1 / 12

Holiday home in Chicago

Illinois / Chicago

3 8 4 nights min stay

House / 3 bedrooms / sleeps 8 / 4 nights min stay

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from £938 / night

£6598 / week

Book

from £938 / night

(1) Excellent 

1 / 16

Holiday condo in Chicago

Illinois / Chicago

2 5 3 nights min stay

Condo / 2 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £347 / night

£2382 / week

Book

from £347 / night

(1) Terrible 

1 / 11

Holiday apartment in Chicago

Illinois / Chicago

2 6 2 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 2 nights min stay

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from £296 / night

£2066 / week

Book

from £296 / night

(1) Excellent 

1 / 23

Holiday home with golf nearby in Chicago

Illinois / Chicago

3 8 2 nights min stay

House / 3 bedrooms / sleeps 8 / 2 nights min stay

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from £487 / night

£2778 - £3473 / week

Book

from £487 / night

1 / 13

Hotel apartment rental in Chicago

Illinois / Chicago

3 8 Min stay varies

Hotel apartment / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £132 / night

£773 - £2135 / week

Book

from £132 / night

1 / 24

Holiday townhouse in Chicago

Illinois / Chicago

3 8 Min stay varies

Townhouse / 3 bedrooms / sleeps 8 / Min stay varies

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from £330 / night

£2698 / week

Book

from £330 / night

1 / 19

Holiday apartment in Chicago

Illinois / Chicago

6 16 Min stay varies

Apartment / 6 bedrooms / sleeps 16 / Min stay varies

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from £174 / night

£3820 / week

Book

from £174 / night

(2) Excellent 

1 / 11

Chicago holiday apartment rental

Illinois / Chicago

2 6 3 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £160 / night

£1114 - £1503 / week

Book

from £160 / night

1 / 14

Holiday apartment in Chicago

Illinois / Chicago

3 8 Min stay varies

Apartment / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £105 / night

£730 / week

Book

from £105 / night

(1) Excellent 

1 / 21

Holiday hotel apartment in Chicago

Illinois / Chicago

1 4 1 night min stay

Hotel apartment / 1 bedroom / sleeps 4 / 1 night min stay

Add to shortlist

from £63 / night

£973 / week

Book

from £63 / night

1 / 21

Holiday apartment in Chicago

Illinois / Chicago

2 12 3 nights min stay

Apartment / 2 bedrooms / sleeps 12 / 3 nights min stay

Add to shortlist

from £208 / night

£1459 / week

Book

from £208 / night

1 / 19

Holiday apartment rental

Illinois / Chicago

2 7 2 nights min stay

Apartment / 2 bedrooms / sleeps 7 / 2 nights min stay

Add to shortlist

from £244 / night

£1702 / week

Book

from £244 / night

1 / 14

Holiday home in Chicago

Illinois / Chicago

3 6 3 nights min stay

House / 3 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £382 / night

£2674 / week

Book

from £382 / night

(2) Excellent 

1 / 10

Apartment rental in Chicago

Illinois / Chicago

1 4 2 nights min stay

Apartment / 1 bedroom / sleeps 4 / 2 nights min stay

Add to shortlist

from £136 / night

£1083 - £1446 / week

Book

from £136 / night

1 / 18

Holiday apartment rental

Illinois / Chicago

2 4 1 night min stay

Apartment / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £261 / night

£1823 / week

Book

from £261 / night

1 / 20

Chicago holiday apartment rental

Illinois / Chicago

5 14 Min stay varies

Apartment / 5 bedrooms / sleeps 14 / Min stay varies

Add to shortlist

from £139 / night

£2778 / week

Book

from £139 / night

1 / 16

Apartment rental in Chicago

Illinois / Chicago

3 6 Min stay varies

Apartment / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £313 / night

£1667 / week

Book

from £313 / night

(1) Excellent 

1 / 9

Holiday condo in Chicago

Illinois / Chicago

3 6 2 nights min stay

Condo / 3 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £132 / night

£834 / week

Book

from £132 / night

1 / 16

Chicago holiday apartment rental

Illinois / Chicago

2 6 3 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £173 / night

£1211 - £1600 / week

Book

from £173 / night

1 / 13

Hotel apartment rental in Chicago

Illinois / Chicago

2 6 Min stay varies

Hotel apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £97 / night

£1806 / week

Book

from £97 / night

(2) Very Good 

1 / 40

Chicago holiday apartment rental

Illinois / Chicago

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £52 / night

£778 - £1021 / week

Book

from £52 / night

(7) Very Good 

1 / 7

Holiday apartment in Chicago

Illinois / Chicago

1 3 1 night min stay

Apartment / 1 bedroom / sleeps 3 / 1 night min stay

Add to shortlist

from £105 / night

£660 - £709 / week

Book

from £105 / night

1 / 6

Holiday condo in Chicago

Illinois / Chicago

3 8 4 nights min stay

Condo / 3 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £167 / night

£1119 / week

Book

from £167 / night

1 / 10

Condo rental in Chicago

Illinois / Chicago

2 4 1 night min stay

Condo / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £139 / night

£1042 / week

Book

from £139 / night

(4) Very Good 

1 / 11

Chicago holiday apartment rental

Illinois / Chicago

2 5 3 nights min stay

Apartment / 2 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £157 / night

£869 / week

Book

from £157 / night

1 / 25

Holiday apartment rental

Illinois / Chicago

2 5 5 nights min stay

Apartment / 2 bedrooms / sleeps 5 / 5 nights min stay

Add to shortlist

from £313 / night

£1389 / week

Book

from £313 / night

(1) Very Good 

1 / 14

Holiday apartment in Chicago

Illinois / Chicago

3 8 2 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £41 / night

£287 / week

Book

from £41 / night

(2) Excellent 

1 / 15

Holiday apartment in Chicago

Illinois / Chicago

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £136 / night

£799 - £1153 / week

Book

from £136 / night

(4) Good 

1 / 9

Apartment rental in Chicago

Illinois / Chicago

3 8 3 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £104 / night

£725 - £900 / week

Book

from £104 / night

1 / 8

Chicago holiday townhouse rental

Illinois / Chicago

3 6 2 nights min stay

Townhouse / 3 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £244 / night

£1563 / week

Book

from £244 / night

1 / 34

Apartment rental in Chicago

Illinois / Chicago

3 11 2 nights min stay

Apartment / 3 bedrooms / sleeps 11 / 2 nights min stay

Add to shortlist

from £174 / night

£1216 / week

Book

from £174 / night

1 / 22

Holiday apartment in Chicago

Illinois / Chicago

3 6 2 nights min stay

Apartment / 3 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £132 / night

£834 / week

Book

from £132 / night

(1) Excellent 

1 / 7

Chicago holiday apartment rental

Illinois / Chicago

1 4 4 nights min stay

Apartment / 1 bedroom / sleeps 4 / 4 nights min stay

Add to shortlist

from £122 / night

£799 / week

Book

from £122 / night

1 / 13

Holiday apartment in Chicago

Illinois / Chicago

2 4 5 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 5 nights min stay

Add to shortlist

from £137 / night

£903 - £1389 / week

Book

from £137 / night

1 / 25

Holiday apartment in Chicago

Illinois / Chicago

2 7 1 night min stay

Apartment / 2 bedrooms / sleeps 7 / 1 night min stay

Add to shortlist

from £70 / night

£348 - £1042 / week

Book

from £70 / night

1 / 47

Holiday apartment in Chicago

Illinois / Chicago

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £80 / night

£556 - £1042 / week

Book

from £80 / night

(1) Poor 

1 / 11

Chicago holiday apartment rental

Illinois / Chicago

2 6 3 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £49 / night

£341 - £855 / week

Book

from £49 / night

(2) Very Good 

1 / 18

Holiday home in Chicago

Illinois / Chicago

3 9 3 nights min stay

House / 3 bedrooms / sleeps 9 / 3 nights min stay

Add to shortlist

from £97 / night

£607 - £801 / week

Book

from £97 / night

(3) Good 

1 / 8

Holiday apartment in Chicago

Illinois / Chicago

2 5 3 nights min stay

Apartment / 2 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £139 / night

£695 / week

Book

from £139 / night

1 / 9

Chicago holiday apartment rental

Illinois / Chicago

2 5 2 nights min stay

Apartment / 2 bedrooms / sleeps 5 / 2 nights min stay

Add to shortlist

from £94 / night

£612 - £903 / week

Book

from £94 / night

1 / 11

Chicago holiday apartment rental

Illinois / Chicago

2 5 2 nights min stay

Apartment / 2 bedrooms / sleeps 5 / 2 nights min stay

Add to shortlist

from £84 / night

£591 - £810 / week

Book

from £84 / night

1 / 8

Apartment rental in Chicago

Illinois / Chicago

2 5 4 nights min stay

Apartment / 2 bedrooms / sleeps 5 / 4 nights min stay

Add to shortlist

from £105 / night

£730 / week

Book

from £105 / night

(1) Excellent 

1 / 21

Holiday home in Chicago

Illinois / Chicago

3 8 2 nights min stay

House / 3 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £122 / night

£695 - £834 / week

Book

from £122 / night

(3) Poor 

1 / 13

Holiday apartment in Chicago

Illinois / Chicago

2 4 4 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 4 nights min stay

Add to shortlist

from £122 / night

£764 / week

Book

from £122 / night

(1) Poor 

1 / 51

Holiday apartment in Chicago

Illinois / Chicago

3 6 3 nights min stay

Apartment / 3 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £134 / night

£794 / week

Book

from £134 / night

1 / 12

Holiday apartment accommodation

Illinois / Chicago

1 3 30 nights min stay

Apartment / 1 bedroom / sleeps 3 / 30 nights min stay

Add to shortlist

from £98 / night

£681 / week

Book

from £98 / night

1 / 10

Holiday condo in Chicago

Illinois / Chicago

2 10 2 nights min stay

Condo / 2 bedrooms / sleeps 10 / 2 nights min stay

Add to shortlist

from £174 / night

£1042 / week

Book

from £174 / night

(2) Poor 

1 / 16

Chicago holiday home rental

Illinois / Chicago

3 8 3 nights min stay

House / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £56 / night

£382 - £875 / week

Book

from £56 / night

1 / 12

Holiday apartment in Chicago

Illinois / Chicago

4 5 3 nights min stay

Apartment / 4 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £139 / night

£695 / week

Book

from £139 / night

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