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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Top guest favourite
Guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
1 bedroom
,
·
2 beds
,
·
1 private bathroom
4–9 Jul
4–9 Jul
$1,098 SGD
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for 5 nights
$1,098 SGD for 5 nights
,
·
4.97 out of 5 average rating, 331 reviews
4.97 (331)
Top guest favourite
Guest favourite
Place to stay in Berwyn
room in family home
1 bedroom
1 bedroom
1 bed
,
·
1 bed
1 bathroom
,
·
1 bathroom
1–6 Dec
1–6 Dec
$346 SGD
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for 5 nights
$346 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Room in Chicago
Private Room in Norwood Park
1 bed
1 bed
1 bathroom
,
·
1 bathroom
14–19 Jun
14–19 Jun
$426 SGD
$343 SGD
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for 5 nights
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Place to stay in Chicago
Private Room for 3 Guests By Grand Ave Blueline
1 bedroom
1 bedroom
2 beds
,
·
2 beds
2 bathrooms
,
·
2 bathrooms
1–6 Jan
1–6 Jan
$566 SGD
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for 5 nights
$566 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom
1 bedroom
1 bed
,
·
1 bed
1 bathroom
,
·
1 bathroom
26 Jun – 1 Jul
26 Jun – 1 Jul
$892 SGD
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for 5 nights
$892 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 163 reviews
4.95 (163)
Top guest favourite
Guest favourite
Flat in Chicago
Ravenswood Guest House Annex
1 bedroom
1 bedroom
3 beds
,
·
3 beds
1 bathroom
,
·
1 bathroom
7–12 Sept
7–12 Sept
$867 SGD
$794 SGD
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for 5 nights
Free cancellation
4.93 out of 5 average rating, 485 reviews
4.93 (485)
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom
1 bedroom
1 bunk bed
,
·
1 bunk bed
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$852 SGD
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for 5 nights
$852 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
North Mayfair Retreat
1 bedroom
1 bedroom
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
17–22 Aug
17–22 Aug
$861 SGD
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for 5 nights
$861 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Guest favourite
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms
3 bedrooms
4 beds
,
·
4 beds
1 bathroom
,
·
1 bathroom
21–26 Sept
21–26 Sept
$822 SGD
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for 5 nights
$822 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 59 reviews
4.9 (59)
Guest favourite
Guest favourite
Room in Chicago
Lovely Front Room in a New Renovated Apartment
2 single beds
2 single beds
1 bathroom
,
·
1 bathroom
9–14 Aug
9–14 Aug
$495 SGD
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for 5 nights
$495 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 99 reviews
4.92 (99)
Guest favourite
Guest favourite
Place to stay in Chicago
The Cozy Scholar's Retreat and Spa Bath
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
10–15 Jul
10–15 Jul
$890 SGD
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for 5 nights
$890 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 14 reviews
4.93 (14)
Top guest favourite
Guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
9–14 Aug
9–14 Aug
$913 SGD
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for 5 nights
$913 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 521 reviews
4.92 (521)
Top guest favourite
Guest favourite
Flat in Chicago
Bridgeport Garden Studio
1 bedroom
1 bedroom
1 sofa bed
,
·
1 sofa bed
2 bathrooms
,
·
2 bathrooms
9–14 Aug
9–14 Aug
$904 SGD
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for 5 nights
$904 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Top guest favourite
Guest favourite
Room in Chicago
Mid City, Vintage, Close to O'Hare Pvt Room
2 double beds
2 double beds
1 bathroom
,
·
1 bathroom
11–16 Aug
11–16 Aug
$731 SGD
$615 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 200 reviews
4.95 (200)
Top guest favourite
Guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms
2 bedrooms
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
23–28 Jul
23–28 Jul
$928 SGD
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for 5 nights
$928 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Top guest favourite
Guest favourite
Room in Chicago
Elegant Tuscan-Inspired Home Near Lincoln Square
1 queen bed
1 queen bed
1 bathroom
,
·
1 bathroom
8–13 Sept
8–13 Sept
$875 SGD
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for 5 nights
$875 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 106 reviews
4.98 (106)
Top guest favourite
Guest favourite
Flat in Chicago
Top-Floor 1BR | Steps to Train + Free Parking
1 bedroom
1 bedroom
2 beds
,
·
2 beds
1 bathroom
,
·
1 bathroom
17–22 Oct
17–22 Oct
$857 SGD
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for 5 nights
$857 SGD for 5 nights
5.0 out of 5 average rating, 70 reviews
5.0 (70)
Top guest favourite
Guest favourite
Flat in Chicago
Delightful Studio in the Heart of Andersonville!
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,016 SGD
$891 SGD
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for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Guest suite in Chicago
Private suite in Lincoln Square
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
1 bathroom
,
·
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$878 SGD
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for 5 nights
$878 SGD for 5 nights
4.97 out of 5 average rating, 471 reviews
4.97 (471)
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