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Search results; Over 1,000 places
Over 1,000 places
Flat in Streeterville
3B Luxury Penthouse w/ Sweeping Views, Pool & Gym
3 beds
3 beds
21–26 Apr
21–26 Apr
$419 SGD
$345 SGD
night
$345 SGD per night, originally $419 SGD
New place to stay
New
Superhost
Superhost
Flat in The Loop
Comfy 2BR-2BTH, Ideally Located!
3 beds
3 beds
21–26 Apr
21–26 Apr
$437 SGD
night
$437 SGD per night
New place to stay
New
Guest favourite
Guest favourite
Flat in Streeterville
2br/2ba, A+ location by Mag mile, views & spacious
4 beds
4 beds
5–10 May
5–10 May
$299 SGD
night
$299 SGD per night
4.94 out of 5 average rating, 257 reviews
4.94 (257)
Hotel in The Loop
Multipurpose work station and ultra-fast WiFi
1 queen bed
1 queen bed
21–26 Apr
21–26 Apr
$178 SGD
night
$178 SGD per night
New place to stay
New
Superhost
Superhost
Flat in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
3 beds
3 beds
30 Jun – 5 Jul
30 Jun – 5 Jul
$649 SGD
night
$649 SGD per night
4.77 out of 5 average rating, 201 reviews
4.77 (201)
Hotel in River North
Playful spirit and sustainable practices
1 queen bed
1 queen bed
18–23 Apr
18–23 Apr
$143 SGD
night
$143 SGD per night
4.5 out of 5 average rating, 160 reviews
4.5 (160)
Superhost
Superhost
Place to stay in River North
Chicago Speakeasy-Style Loft (Room 2B)
2 beds
2 beds
21–26 Oct
21–26 Oct
$173 SGD
night
$173 SGD per night
4.89 out of 5 average rating, 114 reviews
4.89 (114)
Superhost
Superhost
Flat in The Loop
Millennium Park Getaway (2BD)
3 beds
3 beds
20–25 May
20–25 May
$442 SGD
night
$442 SGD per night
4.59 out of 5 average rating, 70 reviews
4.59 (70)
Superhost
Superhost
Flat in The Loop
Cloud9-Indoor Pool, Gym, Rooftop-The Tulip
4 beds
4 beds
18–23 Apr
18–23 Apr
$766 SGD
night
$766 SGD per night
New place to stay
New
Flat in Near North Side
The Bulls' Nest: The Chicago Retreat
22–27 Apr
22–27 Apr
$326 SGD
night
$326 SGD per night
New place to stay
New
Superhost
Superhost
Flat in The Loop
Cozy 2BR-2BA steps from 'The Bean' & Michigan Ave
20–25 Apr
20–25 Apr
$483 SGD
$318 SGD
night
$318 SGD per night, originally $483 SGD
4.9 out of 5 average rating, 136 reviews
4.9 (136)
Superhost
Superhost
Flat in Magnificent Mile
Urban Chic Apartment by the Magnificent Mile
2 queen beds
2 queen beds
23–28 Oct
23–28 Oct
$435 SGD
night
$435 SGD per night
4.94 out of 5 average rating, 213 reviews
4.94 (213)
Superhost
Superhost
Home in Near North Side
503LOFT | Top Floor 5 BED, 2 BA Downtown Loft
3 beds
3 beds
26–31 May
26–31 May
$707 SGD
night
$707 SGD per night
4.85 out of 5 average rating, 81 reviews
4.85 (81)
Superhost
Superhost
Flat in The Loop
Spacious & Stylish 2BR-2BA Apt Steps from The Bean
4 queen beds
4 queen beds
21–26 Apr
21–26 Apr
$527 SGD
$343 SGD
night
$343 SGD per night, originally $527 SGD
4.79 out of 5 average rating, 138 reviews
4.79 (138)
Superhost
Superhost
Flat in The Loop
Modern 3BR Penthouse in the Loop | Roof Deck
4 beds
4 beds
21–26 Apr
21–26 Apr
$469 SGD
$402 SGD
night
$402 SGD per night, originally $469 SGD
4.66 out of 5 average rating, 179 reviews
4.66 (179)
Guest favourite
Guest favourite
Flat in Near North Side
201LOFT | 5 BED, 2.5 BA Downtown Spacious Loft
6 beds
6 beds
23–28 Jun
23–28 Jun
$1,241 SGD
night
$1,241 SGD per night
4.95 out of 5 average rating, 43 reviews
4.95 (43)
Flat in Near North Side
Downtown Riverwalk Music Inspired Loft
3 beds
3 beds
21–26 Apr
21–26 Apr
$299 SGD
night
$299 SGD per night
4.73 out of 5 average rating, 44 reviews
4.73 (44)
Flat in Streeterville
Guest 2 Queen Room at Aloft Chicago Mag Mile
2 queen beds
2 queen beds
18–23 Apr
18–23 Apr
$258 SGD
night
$258 SGD per night
New place to stay
New
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