Search results; Over 1,000 places

Prices include all fees
Hotel in Magnificent Mile
Classic luxury on iconic Michigan Ave
1 king bed
May 25 – 30
ﺩ.ﺇ2,369 for 5 nights
for 5 nights
4.56 out of 5 average rating, 846 reviews
Superhost
Hotel in The Loop
All-glass gem by Chicago architect Harry Weese
1 double bed
May 21 – 26
ﺩ.ﺇ3,988 for 5 nights
for 5 nights
4.77 out of 5 average rating, 108 reviews
Hotel in River North
Playful spirit and sustainable practices
1 queen bed
May 25 – 30
ﺩ.ﺇ2,849 for 5 nights
for 5 nights
4.56 out of 5 average rating, 457 reviews
Hotel in The Loop
A polished, modern affair on iconic Michigan Ave.
1 double bed
May 21 – 26
ﺩ.ﺇ3,229 for 5 nights
for 5 nights
4.75 out of 5 average rating, 216 reviews
Hotel in Magnificent Mile
1927 gem, once home of Capone Speakeasy
2 double beds
May 25 – 30
ﺩ.ﺇ2,765 for 5 nights
for 5 nights
4.59 out of 5 average rating, 209 reviews
Room in Chinatown
Stay with Zhi GuangRetired,
3 min Walk to Chinatown
Jun 7 – 12
ﺩ.ﺇ770 for 5 nights
for 5 nights
New place to stay
Superhost
Room in Chicago
Stay with LydiaUx design,
Cozy Haven Room - Bedroom Near Downtown!
May 23 – 28
ﺩ.ﺇ1,575 for 5 nights, originally ﺩ.ﺇ1,729
for 5 nights
4.87 out of 5 average rating, 23 reviews
Hotel in River North
Onsite spa and indoor/outdoor rooftop bar
1 double bed
May 21 – 26
ﺩ.ﺇ3,116 for 5 nights
for 5 nights
4.45 out of 5 average rating, 62 reviews
Hotel in Near South Side
modern design with VU Skyward rooftop bar
1 double bed
May 25 – 30
ﺩ.ﺇ2,948 for 5 nights
for 5 nights
4.6 out of 5 average rating, 30 reviews
Guest favorite
Room in Chicago
Stay with GenovaLmt, cmldt, hvac,
Sweet Pea - Orange Key - Place 3
Aug 23 – 28
ﺩ.ﺇ595 for 5 nights, originally ﺩ.ﺇ649
for 5 nights
5.0 out of 5 average rating, 8 reviews
Room in Chinatown
Stay with Zhi GuangRetired,
Chinatown Starbucks Coffee 2 min
Jun 8 – 13
ﺩ.ﺇ968 for 5 nights
for 5 nights
New place to stay
Guest favorite
Hotel in West Loop
Light-flooded rooms and city views
1 king bed
May 22 – 27
ﺩ.ﺇ4,654 for 5 nights
for 5 nights
4.92 out of 5 average rating, 66 reviews
Guest favorite
Place to stay in River North
Chicago Speakeasy-Style Loft Space (Room 1A)
Free cancellation
Nov 4 – 9
ﺩ.ﺇ2,217 for 5 nights
for 5 nights
4.88 out of 5 average rating, 607 reviews
Guest favorite
Apartment in The Loop
Panoramic 2BR Penthouse in the Sky | Roof Deck
Free cancellation
Jun 14 – 19
ﺩ.ﺇ11,224 for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Hotel in Streeterville
Signature perks, like indoor pool & 24/7 snacks
1 bed
May 25 – 30
ﺩ.ﺇ2,654 for 5 nights
for 5 nights
New place to stay
Boutique hotel in Near North Side
Gritty Chic River North -- ACME Hotel
Free cancellation
Jan 1 – 6
ﺩ.ﺇ2,347 for 5 nights
for 5 nights
4.82 out of 5 average rating, 121 reviews
Guest favorite
Condo in Near West Side
Modern Design 2bd Garden Condo Near United Center
3 beds
May 25 – 30
ﺩ.ﺇ3,042 for 5 nights
for 5 nights
4.88 out of 5 average rating, 16 reviews
Guest favorite
Apartment in Magnificent Mile
Urban Oasis in Vibrant Gold Coast
Free cancellation
Aug 21 – 26
ﺩ.ﺇ5,999 for 5 nights, originally ﺩ.ﺇ6,666
for 5 nights
4.92 out of 5 average rating, 91 reviews