Search results; Over 1,000 places in Chicago

Guest favorite
Room in Chicago
Stay with Danielle
near festivals & united center
Sep 14 – 19
R5,685 ZAR for 5 nights
4.95 out of 5 average rating, 63 reviews
Guest favorite
Room in Chicago
Stay with TimCoffee,
Convenient Location / Private Room (Queen Bed)
Jul 6 – 11
R8,169 ZAR for 5 nights
4.92 out of 5 average rating, 103 reviews
Guest favorite
Apartment in Berwyn
The Green Bungalow: Charming 1-BR apt. with patio
2 beds
Jul 6 – 11
R10,780 ZAR for 5 nights, originally R14,995 ZAR
4.91 out of 5 average rating, 307 reviews
Apartment in Chicago
Chicago Addison St 2 bed/2 bath condo w/parking
Free cancellation
Aug 17 – 22
R12,274 ZAR for 5 nights
4.46 out of 5 average rating, 13 reviews
Guesthouse in Chicago
Chill 1BR in Shared Coach House - Near Wicker Park
1 bed
Aug 3 – 8
R8,545 ZAR for 5 nights
New place to stay
Guest favorite
Apartment in Cicero
COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Free cancellation
Jul 6 – 11
R14,569 ZAR for 5 nights, originally R17,996 ZAR
4.97 out of 5 average rating, 312 reviews
Room in Chicago
Stay with ⁨Giampiero (John)⁩Self-employed,
Trendy Chicago Apartment Just Steps from the Train
Aug 31 – Sep 5
R6,948 ZAR for 5 nights
New place to stay
Superhost
Room in Oak Park
Stay with RicardoRetired,
Cozy suite
Jul 20 – 25
R7,558 ZAR for 5 nights
4.84 out of 5 average rating, 102 reviews
Superhost
Room in Chicago
Stay with LydiaUx design,
Bohemian Retreat Room – Near Downtown & UC!
Jul 1 – 6
R8,253 ZAR for 5 nights
4.88 out of 5 average rating, 25 reviews
Top guest favorite
Apartment in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Free cancellation
Oct 25 – 30
R14,211 ZAR for 5 nights
5.0 out of 5 average rating, 30 reviews
Guest favorite
Room in Chicago
Stay with TimCoffee,
Fantastic Location / Private Room
Jul 5 – 10
R8,737 ZAR for 5 nights
4.94 out of 5 average rating, 101 reviews
Home in Chicago
LUXURY - Movie Theater + Spa House
Free cancellation
Oct 27 – Nov 1
R15,790 ZAR for 5 nights
New place to stay
Superhost
Apartment in Chicago
The Areal Oasis
2 beds
Jul 6 – 11
R21,495 ZAR for 5 nights, originally R25,135 ZAR
4.92 out of 5 average rating, 50 reviews
Guest favorite
Apartment in Chicago
The Parkside Pavilion
Free cancellation
Aug 16 – 21
R22,548 ZAR for 5 nights, originally R26,392 ZAR
5.0 out of 5 average rating, 15 reviews
Apartment in Chicago
Sunny Penthouse - Oakwood Beach
Free cancellation
Aug 9 – 14
R23,348 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Room in Chicago
Stay with JohnHosting for 6 years,
Edgewater Arts & Crafts Retreat 2
Aug 22 – 27
R6,843 ZAR for 5 nights
4.93 out of 5 average rating, 90 reviews
Top guest favorite
Apartment in Chicago
2 Room Apartment in Vintage Bldg
Free cancellation
Nov 3 – 8
R13,348 ZAR for 5 nights
4.96 out of 5 average rating, 47 reviews
Guest favorite
Room in Oak Park
Stay with LiDesigner,
DT Oak Park LUXE Private BR C | Queen Bed Sleeps 2
Aug 13 – 18
R8,169 ZAR for 5 nights
5.0 out of 5 average rating, 9 reviews