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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
Elegant Suite in Gold Coast
1 bedroom
,
·
2 beds
,
·
1.5 private bathrooms
28 Aug – 2 Sept
28 Aug – 2 Sept
$3,324 SGD
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for 5 nights
$3,324 SGD for 5 nights
,
·
4.98 out of 5 average rating, 208 reviews
4.98 (208)
Guest favourite
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
3–8 Jul
3–8 Jul
$2,379 SGD
$1,384 SGD
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for 5 nights
4.97 out of 5 average rating, 77 reviews
4.97 (77)
Superhost
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
2–7 Jul
2–7 Jul
$4,124 SGD
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for 5 nights
$4,124 SGD for 5 nights
Free cancellation
New place to stay
New
Top 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
25–30 Oct
25–30 Oct
$1,370 SGD
$1,254 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 119 reviews
4.95 (119)
Place to stay in Palatine
Private King Room A | Private Bathroom
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
14–19 Jul
14–19 Jul
$609 SGD
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for 5 nights
$609 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
9–14 Aug
9–14 Aug
$3,574 SGD
$3,038 SGD
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for 5 nights
Book early to save
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Guest favourite
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,558 SGD
$1,299 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Home in Evanston
1/2 mile to NU, 5min walk to Lake, Swim Spa Pool
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
5–10 Jul
5–10 Jul
$6,990 SGD
$4,767 SGD
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for 5 nights
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,291 SGD
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for 5 nights
$2,291 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Top guest favourite
Guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$3,078 SGD
$2,533 SGD
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for 5 nights
5.0 out of 5 average rating, 52 reviews
5.0 (52)
Guest favourite
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$1,882 SGD
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for 5 nights
$1,882 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Superhost
Superhost
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
24–29 Oct
24–29 Oct
$779 SGD
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for 5 nights
$779 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 45 reviews
4.89 (45)
Superhost
Superhost
Flat in Chicago
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
8–13 Jul
8–13 Jul
$6,816 SGD
$5,854 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Room in Chicago
Comfortable bed with Smart stand
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
18–23 Jul
18–23 Jul
$419 SGD
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for 5 nights
$419 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$872 SGD
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for 5 nights
$872 SGD for 5 nights
4.93 out of 5 average rating, 337 reviews
4.93 (337)
Guest favourite
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
14–19 Jul
14–19 Jul
$1,800 SGD
$1,611 SGD
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for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,834 SGD
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for 5 nights
$2,834 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,354 SGD
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for 5 nights
$1,354 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
4–9 Aug
4–9 Aug
$559 SGD
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for 5 nights
$559 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 269 reviews
4.91 (269)
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