Location

Dates

Guests

Vacation rentals in Chicago

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 bedrooms·2 baths

Chicago • Illinois

$187 – $2,000/ night(excl. fees & taxes)

Chic 2-bedroom apartment in beautiful Chicago. 30+ Day Stays Only

2 bedrooms·2 baths

Chicago • Illinois

$134/ night(excl. fees & taxes)

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2 bedrooms·1 bath

Chicago • Illinois

4.97(98 reviews)

$622.12 USD total for 3 nights

Sep 22 – 25, 2026

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

7 bedrooms·3 baths

Chicago • Illinois

$338 – $3,000/ night(excl. fees & taxes)

Step into serenity at our welcoming retreat. Follow detailed check-in directions to unlock the smart lock for secure access. Relax in the cozy living room with a 30" Smart TV and a collection of board games. Outside, unwind in the serene backyard.

Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Unwind in our inviting sanctuary. Seamless check-in with detailed instructions and a smart lock. Cozy up in the relaxing living room, equipped with a 30" Smart TV and a selection of board games. Step outside to a tranquil backyard with a pergola.

Step into tranquility with seamless check-in and a smart lock. Explore local treasures with our custom guidebook. Outside, unwind in the serene backyard oasis, complete with a pergola, fire-pit, outdoor gas grill, and picnic table dining.

Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bedrooms·2½ baths

Chicago • Illinois

5(92 reviews)

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2 bedrooms·1 bath

Chicago • Illinois

$82 – $3,000/ night(excl. fees & taxes)

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

6 bedrooms·4 baths

Chicago • Illinois

$3,600.00 USD total for 3 nights

Sep 22 – 25, 2026

Cozy up in your own private cinema, thoughtfully designed for relaxed evenings and unforgettable movie nights. With stunning 4K visuals and immersive Dolby speakers, it’s the perfect escape into your favorite films.

A vibrant, retro-style space buzzing with energy—perfect for friendly competition and late-night fun. The glowing lights and arcade charm make it a favorite hangout for guests of all ages.

Theater • Game Room • Gym • Firepit • 4BR Home

🍽️ Outdoor dining set

Stay active with a sleek indoor gym designed for convenience and style. Perfect for quick workouts or full sessions, it’s fitness reimagined at home.

Theater • Game Room • Gym • Firepit • 4BR Home

4 bedrooms·2 baths

Chicago • Illinois

$94 – $3,000/ night(excl. fees & taxes)

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

8 bedrooms·3 baths

Chicago • Illinois

$280 – $3,000/ night(excl. fees & taxes)

Chicago Lakefront · Fire Pit Patio · Beach Across image 1

Chicago Lakefront · Fire Pit Patio · Beach Across image 2

To the right: two plush couches and a large window. Opposite you: a mounted TV and a table with four chairs. To the right of the table is a corner desk with a lamp. A large rug anchors the center floor. Simple, clear, and easy to navigate.

Chicago Lakefront · Fire Pit Patio · Beach Across image 4

Chicago Lakefront · Fire Pit Patio · Beach Across image 5

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bedroom·1 bath

Chicago • Illinois

5(1 review)

$447.00 USD $357.60 USD total for 3 nights

Sep 22 – 25, 2026

Living Room with 65" TV

Living Room with 65" TV

Indoor Swim Spa

Charming Garden Retreat

5 bedrooms·3½ baths

Evanston • Illinois

$683 – $2,275/ night(excl. fees & taxes)

Ruby’s Retreat - 4BD/3BA+Office in Western Springs

4 bedrooms·3 baths

Western Springs • Illinois

$185/ night(excl. fees & taxes)

Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

3 bedrooms·2 baths

Lombard • Illinois

$91 – $452/ night(excl. fees & taxes)

Front of the house

Entrance to the unit

Middle Level of the House with Working Space

2 bedrooms·1 bath

Darien • Illinois

4.73(44 reviews)

$93/ night(excl. fees & taxes)

Charming ranch home with vibrant fall views and glowing sunset curb appeal

*King bed *Outdoor Living *Sought-After Area

*King bed *Outdoor Living *Sought-After Area

Charming backyard lounge with cozy deck seating and private garden vibe

Cozy boho lounge with greenery, armchairs, and warm natural accents

King bed Outdoor Living *Sought-After Area

3 bedrooms·1½ baths

Northbrook • Illinois

5(130 reviews)

$1,418.00 USD total for 3 nights

Sep 27 – 30, 2026

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

1 bedroom·1 bath

Arlington Heights • Illinois

$249/ night(excl. fees & taxes)

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 1

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 2

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 3

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 4

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 5

Stylish, Sun-Filled Retreat - Minutes to O’Hare!

2 bedrooms·2 baths

Wheeling • Illinois

$200/ night(excl. fees & taxes)