Search results; Over 1,000 places in Chicago

Hotel in Chicago
Queen Bed | Breakfast Included. No Cleaning Fee
Free cancellation
Jun 1 – 6
$925 for 5 nights
for 5 nights
4.68 out of 5 average rating, 62 reviews
Top guest favorite
Condo in Chicago
Great location. Free parking.
Free cancellation
Aug 10 – 15
$571 for 5 nights
for 5 nights
4.97 out of 5 average rating, 801 reviews
Guest favorite
Shared hotel room in Chicago
Convenient Stay In The Heart of River North
1 single bed
Jun 1 – 6
$280 for 5 nights, originally $320
for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Apartment in Chicago
A Hand-some Place Near Wrigley
1 queen bed
Jun 1 – 6
$737 for 5 nights, originally $1,115
for 5 nights
4.94 out of 5 average rating, 108 reviews
Apartment in Chicago
Uptown Studio Gem
1 queen bed
Jun 1 – 6
$542 for 5 nights
for 5 nights
4.9 out of 5 average rating, 10 reviews
Top guest favorite
Apartment in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Free cancellation
Sep 21 – 26
$770 for 5 nights
for 5 nights
5.0 out of 5 average rating, 19 reviews
Top guest favorite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
Free cancellation
Aug 31 – Sep 5
$884 for 5 nights
for 5 nights
4.99 out of 5 average rating, 362 reviews
Top guest favorite
Apartment in Chicago
Explore Lincoln Park from a Polished Apartment
Free cancellation
Aug 3 – 8
$1,124 for 5 nights
for 5 nights
5.0 out of 5 average rating, 259 reviews
Guest favorite
Apartment in Chicago
1BR/1BA City Comfort
1 queen bed
Jun 2 – 7
$611 for 5 nights, originally $879
for 5 nights
5.0 out of 5 average rating, 12 reviews
Guest favorite
Apartment in Chicago
Dugout in Wrigleyville
1 queen bed
Jun 1 – 6
$656 for 5 nights, originally $736
for 5 nights
4.84 out of 5 average rating, 352 reviews
Hotel in Chicago
Well-appointed king with ADA features
1 king bed
Jun 29 – Jul 4
$492 for 5 nights
for 5 nights
4.66 out of 5 average rating, 68 reviews
Top guest favorite
Guesthouse in Countryside
Cozy Cottage Minutes from Downtown Chicago
Free cancellation
Jun 29 – Jul 4
$747 for 5 nights
for 5 nights
4.94 out of 5 average rating, 484 reviews
Apartment in Chicago
Central 1BR Retreat
1 king bed
Jun 1 – 6
$559 for 5 nights, originally $660
for 5 nights
5.0 out of 5 average rating, 3 reviews
Hotel in Chicago
1927 gem, once home of Capone Speakeasy
2 double beds
Jun 14 – 19
$746 for 5 nights
for 5 nights
4.59 out of 5 average rating, 211 reviews
Guest favorite
Apartment in Maywood
Cozy guest studio, great for couples!
Free cancellation
Jul 20 – 25
$502 for 5 nights
for 5 nights
4.92 out of 5 average rating, 93 reviews
Hotel in Chicago
modern design with VU Skyward rooftop bar
1 double bed
Jun 29 – Jul 4
$613 for 5 nights
for 5 nights
4.61 out of 5 average rating, 31 reviews
Top guest favorite
Apartment in Evanston
Charming, Sunny Apartment with Backyard Garden
Free cancellation
Sep 14 – 19
$749 for 5 nights, originally $839
for 5 nights
4.97 out of 5 average rating, 495 reviews
Guest favorite
Apartment in Chicago
Stylish Studio in Uptown Chicago
1 queen bed
Jun 1 – 6
$556 for 5 nights, originally $947
for 5 nights
5.0 out of 5 average rating, 5 reviews