Over 1,000 places in Countryside

Guest favorite
Guesthouse in Countryside
Cozy Cottage Minutes from Downtown Chicago
1 queen bed
Apr 23 – 28
4.94 out of 5 average rating, 396 reviews
Apartment in Countryside
Cozy modern 1st floor apartment
Apr 7 – 12
New place to stay
Guest favorite
Room in Western Springs
Stay with TaiaHosting for 6 years,
My Home & Garden
Apr 1 – 6
5.0 out of 5 average rating, 50 reviews
Apartment in Countryside
Updated One Bedroom on first floor
1 bed
Jun 1 – 6
4.6 out of 5 average rating, 15 reviews
Apartment in Countryside
Cozy updated one bedroom on first floor
Jun 14 – 19
4.6 out of 5 average rating, 43 reviews
Guest favorite
Tiny home in Burr Ridge
Less is more! Pet friendly Tiny Home near Chicago!
2 beds
Apr 7 – 12
4.92 out of 5 average rating, 226 reviews
Guest favorite
Apartment in Palos Hills
Aunt Linda's Apartment with a View in Palos
4 beds
Apr 1 – 7
4.93 out of 5 average rating, 152 reviews
Guest favorite
Apartment in Oak Park
The Artist's Loft - Oak Park
3 beds
Apr 14 – 19
4.94 out of 5 average rating, 18 reviews
Apartment in Chicago
Classic Chi Apt- Walk to El
2 beds
Apr 7 – 12
New place to stay
Guest favorite
Apartment in Chicago
Designer Apt: Easy Parking/20min MagMile & Wrigley
2 queen beds
Apr 15 – 20
5.0 out of 5 average rating, 46 reviews
Guest favorite
Home in Justice
3 Kng|1 Qn|1 Full|3AirBds|Basketball Crt|FreePark
5 beds
Apr 21 – 26
4.95 out of 5 average rating, 188 reviews
Guest favorite
Camper/RV in Willow Springs
Wander Willow Springs Glamping Retreat
1 bed
Apr 1 – 6
4.97 out of 5 average rating, 39 reviews
Apartment in Chicago
Large 3BR/2BA Wicker Park Apt +Free Garage Parking
3 beds
Apr 21 – 26
5.0 out of 5 average rating, 3 reviews
Apartment in Brookfield
Cozy, Clean, and Affordable!
2 beds
Apr 2 – 7
New place to stay
Guest favorite
Home in Chicago
Large 3BD/2.5 BA by Lakefront - Long stays welcome
3 beds
Apr 12 – 17
4.97 out of 5 average rating, 90 reviews
Guest favorite
Condo in Clarendon Hills
Apartment in Clarendon Hills.
3 beds
Apr 8 – 13
5.0 out of 5 average rating, 37 reviews
Guest favorite
Apartment in Lyons
Beautiful & Private, 1bdrm, 1bath w/washer & dryer
2 beds
Apr 1 – 6
5.0 out of 5 average rating, 12 reviews
Guest favorite
Apartment in Oak Park
The Chicago Game Room (Oak Park, IL)
7 beds
May 4 – 9
4.97 out of 5 average rating, 72 reviews