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

$4,040.74 USD total for 3 nights

Nov 6 – 9, 2026

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

2 bedrooms·2 baths

Chicago • Illinois

$4,170.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Bright and inviting living room with a spacious sectional sofa, perfect for relaxing after a day of exploring Chicago. Floor-to-ceiling mirrored walls create an open, airy feel, while large windows fill the space with natural light.

3BR Vintage Apt • Back Yard• Walk to McKinley Park image 2

3BR Vintage Apt • Back Yard• Walk to McKinley Park image 3

Hand-painted vine and fruit mural along the upper wall near the ceiling, adding a distinctive decorative accent to the space.

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3 bedrooms·1 bath

Chicago • Illinois

4.92(25 reviews)

$646.25 USD total for 3 nights

Nov 8 – 11, 2026

Chicago Getaway | Cozy 2BR Near Downtown

Thoughtful extras: coffee bar, games, full cookware & pet-friendly perks

Chicago Getaway | Cozy 2BR Near Downtown

Chicago Getaway | Cozy 2BR Near Downtown

Bright living space with hardwood floors and wall-mounted streaming TV

Chicago Getaway | Cozy 2BR Near Downtown

2 bedrooms·1 bath

Chicago • Illinois

$79 – $796/ 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)

$491.73 USD total for 3 nights

Nov 9 – 12, 2026

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

4.9(106 reviews)

$1,465.00 USD total for 3 nights

Nov 6 – 9, 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

$1,214.01 USD total for 3 nights

Nov 6 – 9, 2026

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

Nov 6 – 9, 2026

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

6 bedrooms·3 baths

Chicago • Illinois

$1,100.00 USD total for 3 nights

Nov 9 – 12, 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

$2,177.92 USD total for 3 nights

Nov 6 – 9, 2026

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

$4,957.63 USD total for 3 nights

Nov 6 – 9, 2026

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)

$467.00 USD $373.60 USD total for 3 nights

Nov 8 – 11, 2026

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

4 bedrooms·3 baths

Western Springs • Illinois

$6,506.85 USD $5,908.67 USD total for 30 nights

Aug 28 – Sep 27, 2027

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

$1,173.01 USD total for 3 nights

Nov 6 – 9, 2026

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)

$494.76 USD total for 4 nights

Nov 6 – 10, 2026

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(135 reviews)

$1,492.00 USD total for 3 nights

Nov 19 – 22, 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

$806.76 USD total for 3 nights

Nov 6 – 9, 2026

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

$625.00 USD total for 3 nights

Nov 6 – 9, 2026