Search results; Over 1,000 places in Chicago

Superhost
Hotel in Chicago
All-glass gem by Chicago architect Harry Weese
1 double bed
Jun 11 – 16
$1,457 for 5 nights
for 5 nights
4.8 out of 5 average rating, 155 reviews
Hotel in Chicago
Classic luxury on iconic Michigan Ave
1 king bed
Jun 15 – 20
$1,178 for 5 nights
for 5 nights
4.56 out of 5 average rating, 875 reviews
Hotel in Chicago
Double Beds | Breakfast Included. No Cleaning Fee
Free cancellation
Aug 17 – 22
$758 for 5 nights
for 5 nights
4.59 out of 5 average rating, 75 reviews
Guest favorite
Hotel in Rosemont
Relaxing Standard Room l Free Airport Shuttle
1 queen bed
Jun 8 – 13
$852 for 5 nights
for 5 nights
4.93 out of 5 average rating, 257 reviews
Hotel in Chicago
A polished, modern affair on iconic Michigan Ave.
1 double bed
Jun 11 – 16
$1,066 for 5 nights
for 5 nights
4.76 out of 5 average rating, 244 reviews
Guest favorite
Apartment in Chicago
Logan Square Garden Sanctuary
Free cancellation
Jun 30 – Jul 5
$816 for 5 nights
for 5 nights
4.93 out of 5 average rating, 126 reviews
Shared hotel room in Chicago
Convenient Stay In The Heart of River North
1 single bed
Jun 10 – 15
$303 for 5 nights, originally $348
for 5 nights
4.74 out of 5 average rating, 19 reviews
Superhost
Apartment in Chicago
Sunny chic Avondale 4 bed 3 bath
4 beds
Jun 8 – 13
$1,282 for 5 nights, originally $1,518
for 5 nights
New place to stay
Guesthouse in Chicago
Andersonville Luxury Pool Escape
1 bed
Jun 8 – 13
$2,396 for 5 nights
for 5 nights
New place to stay
Guest favorite
Room in Des Plaines
Stay with ValentinBuilder,
R2 Cozy room in a convenient location by a river
Jun 9 – 14
$393 for 5 nights
for 5 nights
4.88 out of 5 average rating, 442 reviews
Top guest favorite
Apartment in Chicago
2B Midcentury Artist Loft w King Bed
2 beds
Jun 8 – 13
$852 for 5 nights, originally $1,085
for 5 nights
5.0 out of 5 average rating, 11 reviews
Top guest favorite
Apartment in Hickory Hills
Cozy Guest Suite. Private Entry+ Turo Rental
Free cancellation
Aug 4 – 9
$665 for 5 nights, originally $725
for 5 nights
4.95 out of 5 average rating, 41 reviews
Apartment in Chicago
Updated, Prime Location, Parking Avail. - LP
1 bed
Jun 15 – 20
$746 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Apartment in Chicago
Renovated Loft on Milwaukee Ave
3 beds
Jul 6 – 11
$892 for 5 nights, originally $1,402
for 5 nights
5.0 out of 5 average rating, 36 reviews
Top guest favorite
Apartment in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Free cancellation
Oct 25 – 30
$770 for 5 nights
for 5 nights
5.0 out of 5 average rating, 25 reviews
Superhost
Apartment in Cicero
private 2BedroomAPt/Garage park/ Close to City
2 beds
Jun 15 – 20
$577 for 5 nights
for 5 nights
4.65 out of 5 average rating, 173 reviews
Apartment in Chicago
Avondale Attic Nook
2 beds
Jun 14 – 19
$628 for 5 nights
for 5 nights
New place to stay
Home in Chicago
Gorgeous home, 3BR/2BA, Free Parking, Free Laundry
2 beds
Jun 8 – 13
$1,132 for 5 nights
for 5 nights
New place to stay