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Search results; Over 1,000 homes in Chicago
Over 1,000 homes in Chicago
Guest favourite
Guest favourite
Apartment in Chicago
The Upscale Getaway Near Downtown
2 bedrooms
,
·
3 beds
,
·
2 private bathrooms
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,883 SGD
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for 5 nights
$2,883 SGD for 5 nights
,
·
4.93 out of 5 average rating, 290 reviews
4.93 (290)
Guest favourite
Guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
8–13 Aug
8–13 Aug
$1,219 SGD
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for 5 nights
$1,219 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Flat in Oak Park
Treetop Oasis With Parking Walkable To Town+Train
2 bedrooms
2 bedrooms
4 beds
,
·
4 beds
28 Jun – 3 Jul
28 Jun – 3 Jul
$1,845 SGD
$1,464 SGD
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for 5 nights
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Free cancellation
4.97 out of 5 average rating, 79 reviews
4.97 (79)
Guest favourite
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom
1 bedroom
1 queen bed
,
·
1 queen bed
3–8 Aug
3–8 Aug
$3,385 SGD
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for 5 nights
$3,385 SGD for 5 nights
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Free cancellation
4.98 out of 5 average rating, 56 reviews
4.98 (56)
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
21–26 Jun
21–26 Jun
$1,957 SGD
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for 5 nights
$1,957 SGD for 5 nights
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Free cancellation
New place to stay
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Superhost
Superhost
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
19–24 Jul
19–24 Jul
$1,918 SGD
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for 5 nights
$1,918 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Flat in Chicago
Garden Retreat Pilsen Chicago Apartment
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
29 Jun – 4 Jul
29 Jun – 4 Jul
$1,296 SGD
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for 5 nights
$1,296 SGD for 5 nights
New place to stay
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Top guest favourite
Guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms
4 bedrooms
4 beds
,
·
4 beds
5–10 Jul
5–10 Jul
$2,941 SGD
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for 5 nights
$2,941 SGD for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Superhost
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms
4 bedrooms
3 beds
,
·
3 beds
26–31 Jul
26–31 Jul
$2,306 SGD
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for 5 nights
$2,306 SGD for 5 nights
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Free cancellation
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom
1 bedroom
1 bunk bed
,
·
1 bunk bed
15–20 Aug
15–20 Aug
$913 SGD
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$913 SGD for 5 nights
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Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
9–14 Aug
9–14 Aug
$1,363 SGD
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for 5 nights
$1,363 SGD for 5 nights
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Free cancellation
4.97 out of 5 average rating, 61 reviews
4.97 (61)
Top guest favourite
Guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms
2 bedrooms
3 beds
,
·
3 beds
24–29 Jul
24–29 Jul
$3,173 SGD
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for 5 nights
$3,173 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Top guest favourite
Guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom
1 bedroom
1 king bed
,
·
1 king bed
20–25 Oct
20–25 Oct
$685 SGD
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for 5 nights
$685 SGD for 5 nights
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Free cancellation
5.0 out of 5 average rating, 50 reviews
5.0 (50)
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms
3 bedrooms
6 beds
,
·
6 beds
21–26 Jun
21–26 Jun
$2,926 SGD
$2,641 SGD
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for 5 nights
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Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms
3 bedrooms
3 beds
,
·
3 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,272 SGD
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for 5 nights
$2,272 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Home in Chicago
Steps to Lake & Beach! Multi-Level Oakland Haven
4 bedrooms
4 bedrooms
5 beds
,
·
5 beds
29 Jun – 4 Jul
29 Jun – 4 Jul
$3,776 SGD
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for 5 nights
$3,776 SGD for 5 nights
New place to stay
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Top guest favourite
Guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms
3 bedrooms
3 queen beds
,
·
3 queen beds
28 Jun – 3 Jul
28 Jun – 3 Jul
$2,261 SGD
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for 5 nights
$2,261 SGD for 5 nights
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 299 reviews
4.99 (299)
Guest favourite
Guest favourite
Home in Oak Park
Spacious Oak Park 4bd/3.5ba and Parking
4 bedrooms
4 bedrooms
5 beds
,
·
5 beds
28 Jun – 3 Jul
28 Jun – 3 Jul
$3,057 SGD
$2,564 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.88 out of 5 average rating, 66 reviews
4.88 (66)
Top guest favourite
Guest favourite
Flat in Oak Park
Historic Hotspot: Downtown Oak Park w/parking spot
2 bedrooms
2 bedrooms
2 queen beds
,
·
2 queen beds
12–17 Jul
12–17 Jul
$1,653 SGD
$1,248 SGD
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for 5 nights
4.99 out of 5 average rating, 80 reviews
4.99 (80)
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