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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Guest favourite
Guest favourite
Flat in Chicago
Upscale High-Rise Apt · Rooftop Pool + Views
1 bedroom
,
·
1 bed
,
·
1 private bathroom
11–16 Dec
11–16 Dec
$1,142 SGD
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for 5 nights
$1,142 SGD for 5 nights
,
·
4.91 out of 5 average rating, 46 reviews
4.91 (46)
Featured hotel
Featured hotel
Room in Chicago
Studio suite
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$2,323 SGD
Show price breakdown
for 5 nights
$2,323 SGD for 5 nights
+$324 SGD Airbnb credit
Featured hotel
Featured hotel
Room in Chicago
Level studio suite
1 bathroom
1 bathroom
3–8 Oct
3–8 Oct
$2,845 SGD
Show price breakdown
for 5 nights
$2,845 SGD for 5 nights
+$403 SGD Airbnb credit
Featured hotel
Featured hotel
Hotel in Chicago
Deluxe double
1 bedroom
1 bedroom
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
17–22 Sept
17–22 Sept
$3,888 SGD
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for 5 nights
$3,888 SGD for 5 nights
+$583 SGD Airbnb credit
4.92 out of 5 average rating, 61 reviews
4.92 (61)
Guest favourite
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
18–23 Jan
18–23 Jan
$975 SGD
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for 5 nights
$975 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 132 reviews
4.95 (132)
Top guest favourite
Guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
15–20 Nov
15–20 Nov
$1,316 SGD
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for 5 nights
$1,316 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 39 reviews
4.97 (39)
Top guest favourite
Guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$2,231 SGD
$1,562 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Top guest favourite
Guest favourite
Flat in Chicago
Prime Logan Square apartment
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,649 SGD
$1,456 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 43 reviews
4.98 (43)
Top guest favourite
Guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,024 SGD
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for 5 nights
$2,024 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Guest favourite
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
25–30 Oct
25–30 Oct
$1,866 SGD
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for 5 nights
$1,866 SGD for 5 nights
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
15–20 Nov
15–20 Nov
$1,683 SGD
Show price breakdown
for 5 nights
$1,683 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,369 SGD
Show price breakdown
for 5 nights
$1,369 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 73 reviews
4.97 (73)
Top guest favourite
Guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
15–20 Nov
15–20 Nov
$2,225 SGD
$1,946 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 61 reviews
5.0 (61)
Featured hotel
Featured hotel
Room in Chicago
Deluxe king non smoking
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,862 SGD
Show price breakdown
for 5 nights
$1,862 SGD for 5 nights
+$242 SGD Airbnb credit
4.91 out of 5 average rating, 11 reviews
4.91 (11)
Top guest favourite
Guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$2,042 SGD
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for 5 nights
$2,042 SGD for 5 nights
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Guest favourite
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,213 SGD
$1,919 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 74 reviews
4.95 (74)
Guest favourite
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
23–28 Oct
23–28 Oct
$1,183 SGD
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for 5 nights
$1,183 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 74 reviews
4.92 (74)
Top guest favourite
Guest favourite
Flat in Oak Park
Oak Park Chic Duplex King Bed•Parking•Deck•Yard
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
11–16 Nov
11–16 Nov
$2,738 SGD
$2,339 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 97 reviews
5.0 (97)
Top guest favourite
Guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,517 SGD
Show price breakdown
for 5 nights
$1,517 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 361 reviews
4.99 (361)
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