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Guest favourite
Flat in Old Town
Magical Treehouse Located in HEART of Old Town!
15 guests5 bedrooms6 beds2 bathrooms
18–23 May
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18–23 May
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$4,845 SGD for 5 nights
for 5 nights

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Flat in Chicago
Modern Midway Stay
2 beds
9–14 May
$648 SGD for 5 nights
for 5 nights
New place to stay
Superhost
Hotel in Chicago
All-glass gem by Chicago architect Harry Weese
1 double bed
8–13 May
$966 SGD for 5 nights
for 5 nights
4.73 out of 5 average rating, 75 reviews
Guest favourite
Shared hotel room in Chicago
Convenient Stay In The Heart of River North
1 single bed
11–16 May
$301 SGD for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favourite
Room in Chicago
Stay with ErikHosting for 11 years,
The Red Room
4–9 Aug
$311 SGD for 5 nights
for 5 nights
4.85 out of 5 average rating, 385 reviews
Guest favourite
Room in Oak Park
Stay with JeffreyHosting for 7 years,
Victorian Gem in Heart of FLW District/2nd floor
19–24 May
$741 SGD for 5 nights
for 5 nights
4.88 out of 5 average rating, 200 reviews
Guest favourite
Room in Chicago
Stay with CordaroTraffic services,
Ideal West Beverly Gem (Private RM #2)
26–31 May
$512 SGD for 5 nights
for 5 nights
4.88 out of 5 average rating, 8 reviews
Guest favourite
Hotel in Rosemont
Relaxing Standard Room l Free Airport Shuttle
1 queen bed
8–13 May
$835 SGD for 5 nights
for 5 nights
4.93 out of 5 average rating, 229 reviews
Top guest favourite
Room in Elmhurst
Stay with JanParent to four kids,
Chic Oasis near Downtown Chicago
13–18 Jul
$847 SGD for 5 nights
for 5 nights
4.99 out of 5 average rating, 213 reviews
Room in Chicago
Stay with Zhi GuangRetired,
2 min to Chinatown 3 to Downtown
25–30 May
$343 SGD for 5 nights
for 5 nights
New place to stay
Room in Chicago
Stay with Zhi GuangRetired,
2 min to Downtown 2 min Chinatown
14–19 Jun
$342 SGD for 5 nights
for 5 nights
New place to stay
Guest favourite
Guest suite in Forest View
NEW! Private Guest Suite 5 min from MDW Airport!
1 queen bed
9–14 May
$877 SGD for 5 nights
for 5 nights
5.0 out of 5 average rating, 61 reviews
Room in Chicago
Stay with GenovaLmt, cmldt, hvac,
Glimmer - Blue Key - Place 2
23–28 Jun
$269 SGD for 5 nights
for 5 nights
4.8 out of 5 average rating, 5 reviews
Room in Chicago
Stay with Red Robin RentalsProperty rental,
Modern co-living w/ private balcony near UChicago
8–13 May
$633 SGD for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Oak Park
Stay with Tom And GraceHosting for 11 years,
Antique Filled Home
25–30 May
$549 SGD for 5 nights
for 5 nights
4.95 out of 5 average rating, 374 reviews
Guest favourite
Room in Oak Park
Stay with LiDesigner,
DT Oak Park LUXE Private BR C | Queen Bed Sleeps 2
25–30 May
$534 SGD for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favourite
Room in Chicago
Stay with MarcosHosting for 6 years,
Hattie’s House
9–14 May
$509 SGD for 5 nights
for 5 nights
4.93 out of 5 average rating, 160 reviews
Top guest favourite
Room in Chicago
Stay with Hanna
Cozy art-filled Hyde Park apt
16–21 Jun
$718 SGD for 5 nights
for 5 nights
5.0 out of 5 average rating, 8 reviews
Hotel in Chicago
Well-appointed king with ADA features
1 king bed
29 Jun – 4 Jul
$666 SGD for 5 nights
for 5 nights
4.66 out of 5 average rating, 61 reviews