Location

Dates

Guests

Vacation rentals in Chicago, Illinois, United States

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

681,72 $ USD total por 3 noites

20/10/2026 – 23/10/2026

2BR w/ Workspace + Coffee Bar • Near Transit

2BR w/ Workspace + Coffee Bar • Near Transit

2BR w/ Workspace + Coffee Bar • Near Transit

2BR w/ Workspace + Coffee Bar • Near Transit

2BR w/ Workspace + Coffee Bar • Near Transit

2BR w/ Workspace + Coffee Bar • Near Transit

2 bedrooms·1 bath

Chicago • Illinois

681,72 $ USD total por 3 noites

20/10/2026 – 23/10/2026

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

6 bedrooms·4 baths

Chicago • Illinois

3600,00 $ USD total por 3 noites

20/10/2026 – 23/10/2026

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

1100,00 $ USD total por 3 noites

20/10/2026 – 23/10/2026

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

1101,10 $ USD total por 3 noites

20/10/2026 – 23/10/2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

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

2181,50 $ USD total por 3 noites

20/10/2026 – 23/10/2026

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 por 3 noites

25/10/2026 – 28/10/2026

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

2 bedrooms·1 bath

Elmwood Park • Illinois

4.63(8 reviews)

1200,00 $ USD 1095,00 $ USD total por 7 noites

20/10/2026 – 27/10/2026

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

2 bedrooms·1 bath

Elmwood Park • Illinois

4.5(4 reviews)

30 120,00 $ USD 18 120,00 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

2 bedrooms·1 bath

Elmwood Park • Illinois

5(2 reviews)

30 150,00 $ USD 25 650,00 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

2 bedrooms·1 bath

Elmwood Park • Illinois

5(3 reviews)

30 150,00 $ USD 25 650,00 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

1 bedroom·1 bath

Elmwood Park • Illinois

4699,91 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Top Rated Condo • King Bed • Safe Historic Location

Top Rated Condo • King Bed • Safe Historic Location

Top Rated Condo • King Bed • Safe Historic Location

Top Rated Condo • King Bed • Safe Historic Location

Top Rated Condo • King Bed • Safe Historic Location

Top Rated Condo • King Bed • Safe Historic Location

2 bedrooms·1 bath

Elmwood Park • Illinois

4327,24 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Elmwood Park 2 BR Condo (Great for Kids!)

Elmwood Park 2 BR Condo (Great for Kids!)

Elmwood Park 2 BR Condo (Great for Kids!)

Elmwood Park 2 BR Condo (Great for Kids!)

Elmwood Park 2 BR Condo (Great for Kids!)

Elmwood Park 2 BR Condo (Great for Kids!)

2 bedrooms·1 bath

Elmwood Park • Illinois

4378,87 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Top Rated Condo • 65” TV • Family-friendly 2BR

Top Rated Condo • 65” TV • Family-friendly 2BR

Top Rated Condo • 65” TV • Family-friendly 2BR

Top Rated Condo • 65” TV • Family-friendly 2BR

Top Rated Condo • 65” TV • Family-friendly 2BR

Top Rated Condo • 65” TV • Family-friendly 2BR

2 bedrooms·1 bath

Elmwood Park • Illinois

4404,69 $ USD total por 30 noites

20/10/2026 – 19/11/2026

Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

2 bedrooms·1 bath

Elmwood Park • Illinois

4180,19 $ USD total por 30 noites

20/10/2026 – 19/11/2026

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

3 bedrooms·2 baths

Chicago • Illinois

978,43 $ USD total por 3 noites

20/10/2026 – 23/10/2026

Master Bedroom 2nd floor

1500Main EVANSTON

1500Main EVANSTON

2 bedrooms·1½ baths

Evanston • Illinois

5(166 reviews)

1140,42 $ USD total por 4 noites

01/11/2026 – 05/11/2026

Living Room with 65" TV

Living Room with 65" TV

Indoor Swim Spa

Charming Garden Retreat

5 bedrooms·3½ baths

Evanston • Illinois

3563,77 $ USD total por 3 noites

20/10/2026 – 23/10/2026

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2 bedrooms·1 bath

Chicago • Illinois

711,48 $ USD total por 3 noites

20/10/2026 – 23/10/2026

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

1 bedroom·1 bath

Chicago • Illinois

615,05 $ USD total por 3 noites

20/10/2026 – 23/10/2026

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

1 bedroom·1 bath

Chicago • Illinois

718,03 $ USD total por 4 noites

20/10/2026 – 24/10/2026

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

1 bedroom·1 bath

Chicago • Illinois

686,78 $ USD total por 4 noites

20/10/2026 – 24/10/2026