Search results; 391 places in Chicago Loop

Guest favorite
Condo in Chicago
10 Mins Downtown Free Parking Ping-Pong Sleeps 10
6 beds
May 11 – 16
ﺩ.ﺇ3,539 for 5 nights, originally ﺩ.ﺇ7,142
for 5 nights
4.95 out of 5 average rating, 120 reviews
Apartment in Chicago
Cozy 1BR in South Loop | Convenience in the City
Free cancellation
Jul 4 – 9
ﺩ.ﺇ3,362 for 5 nights
for 5 nights
4.72 out of 5 average rating, 127 reviews
Guest favorite
Apartment in Chicago
51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
4 beds
May 9 – 14
ﺩ.ﺇ8,042 for 5 nights, originally ﺩ.ﺇ12,696
for 5 nights
4.9 out of 5 average rating, 31 reviews
Guest favorite
Place to stay in Chicago
McCormick331, Chinatown, SOX, GrantPark
1 queen bed
Jun 8 – 13
ﺩ.ﺇ2,290 for 5 nights
for 5 nights
4.92 out of 5 average rating, 99 reviews
Guest favorite
Apartment in Chicago
Urban Oasis in Vibrant Gold Coast
Free cancellation
Aug 18 – 23
ﺩ.ﺇ5,933 for 5 nights, originally ﺩ.ﺇ6,592
for 5 nights
4.92 out of 5 average rating, 90 reviews
Guest favorite
Apartment in Chicago
Stunning Basement Apartment w/free street parking!
2 beds
May 9 – 14
ﺩ.ﺇ3,638 for 5 nights
for 5 nights
4.89 out of 5 average rating, 87 reviews
0 of 0 items showing
1 of 3 pages
Show more homes

More stays available for your dates

Guest favorite
Apartment in Chicago
Lincoln Park Coach House w Kitchen & Queen Sleeper
3 beds
May 10 – 15
ﺩ.ﺇ3,344 for 5 nights, originally ﺩ.ﺇ4,639
for 5 nights
4.81 out of 5 average rating, 63 reviews
Top guest favorite
Apartment in Chicago
Millennium park 10 min Free P-Spot&Balcony Sleep 8
4 beds
May 19 – 25
ﺩ.ﺇ8,414 for 6 nights
for 6 nights
4.98 out of 5 average rating, 102 reviews
Guest favorite
Apartment in Chicago
Gold Coast Pristine 3BD|2BR| Patio |Parking| Views
3 beds
Jun 1 – 6
ﺩ.ﺇ16,530 for 5 nights
for 5 nights
4.97 out of 5 average rating, 60 reviews
Top guest favorite
Apartment in Chicago
KING bed FREE P-Spot EV EZZY Accessible NO stairs
4 beds
May 19 – 25
ﺩ.ﺇ8,627 for 6 nights
for 6 nights
4.99 out of 5 average rating, 132 reviews
Superhost
Apartment in Chicago
Pristine Gold Coast 3BD|2BA | Free Parking| Beach
3 beds
May 10 – 15
ﺩ.ﺇ10,245 for 5 nights
for 5 nights
New place to stay
Apartment in Chicago
Stunning Gold Coast Studio
Free cancellation
Jul 9 – 14
ﺩ.ﺇ4,343 for 5 nights
for 5 nights
4.83 out of 5 average rating, 6 reviews
Guest favorite
Apartment in Chicago
Luxury Lincoln Park Retreat 2BR 2LR Dublex
2 beds
May 9 – 14
ﺩ.ﺇ5,881 for 5 nights, originally ﺩ.ﺇ9,190
for 5 nights
4.88 out of 5 average rating, 17 reviews
Top guest favorite
Home in Chicago
NEW! Lake & Skyline View on Kenwood Culdesac!
Free cancellation
Jun 22 – 27
ﺩ.ﺇ10,547 for 5 nights
for 5 nights
5.0 out of 5 average rating, 71 reviews
Superhost
Apartment in Chicago
Luxury Designer Penthouse NW | Pool | Gold Coast
6 beds
May 18 – 23
ﺩ.ﺇ9,639 for 5 nights, originally ﺩ.ﺇ10,890
for 5 nights
New place to stay
Top guest favorite
Apartment in Chicago
Elegant Suite in Gold Coast
Free cancellation
Jun 30 – Jul 5
ﺩ.ﺇ6,739 for 5 nights
for 5 nights
4.98 out of 5 average rating, 150 reviews
Guest favorite
Place to stay in Chicago
McCormick333, Chinatown, SOX, GrantPark
1 queen bed
May 9 – 14
ﺩ.ﺇ2,472 for 5 nights
for 5 nights
4.95 out of 5 average rating, 88 reviews
Apartment in Chicago
3BR Luxury Modern Apartment
3 beds
May 9 – 14
ﺩ.ﺇ7,030 for 5 nights, originally ﺩ.ﺇ11,775
for 5 nights
4.79 out of 5 average rating, 24 reviews