Location

Dates

Guests

Vacation rentals in Glen Ellyn, Illinois, United States

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

2 bedrooms·1 bath

Chicago • Illinois

$2,913.05 USD total for 31 nights

Nov 3 – Dec 4, 2026

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

2 bedrooms·1 bath

Chicago • Illinois

$2,771.40 USD total for 31 nights

Jan 26 – Feb 26, 2027

Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

3 bedrooms·1 bath

Chicago • Illinois

$2,931.05 USD total for 31 nights

Dec 8, 2026 – Jan 8, 2027

Cozy private deck with cushioned seating and a stylish fire table

Prime Chicago base—minutes to Mag Mile, Navy Pier, parks & airports.

Bright living room with recliners, fireplace, TV, and abundant natural light

Spa-style jetted soaking tub for a relaxing, luxurious stay

Cozy fire table patio with wine—perfect for relaxing evening nights

Chicago Oasis | Spa Bath, Patio & Fireplace

1 bedroom·1 bath

Chicago • Illinois

$609.98 USD total for 3 nights

Nov 3 – 6, 2026

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)

$535.93 USD total for 3 nights

Nov 9 – 12, 2026

Imagine enjoying your Chicago vacation in this comfortably furnished living room, equipped with a 80-inch smart TV, you will be able to enjoy movie nights, sports games, and more with family & friends. Comes with Netflix included.

Central | BBQ Deck | Family-Friendly Pueblo Magíco

Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!

Central | BBQ Deck | Family-Friendly Pueblo Magíco

Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!

Central | BBQ Deck | Family-Friendly Pueblo Magíco

5 bedrooms·2 baths

Chicago • Illinois

$1,051.00 USD total for 3 nights

Nov 3 – 6, 2026

Bright & Cozy 1 Bdrm • Free Parking image 1

Bright & Cozy 1 Bdrm • Free Parking image 2

Bright & Cozy 1 Bdrm • Free Parking image 3

Bright & Cozy 1 Bdrm • Free Parking image 4

Bright & Cozy 1 Bdrm • Free Parking image 5

Bright & Cozy 1 Bdrm • Free Parking

1 bedroom·1 bath

Chicago • Illinois

4.61(64 reviews)

$462.00 USD total for 3 nights

Nov 4 – 7, 2026

Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!

Movie Room, Garden Oasis in Central Manor

Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!

check out what people are saying!

Enjoy the natural light, and artwork while enjoying your stay in Chicago!

Movie Room, Garden Oasis in Central Manor

3 bedrooms·2 baths

Chicago • Illinois

$804.00 USD total for 3 nights

Nov 3 – 6, 2026

Space for relaxing and a table for everyone

Gourmet chef's kitchen & space for all!

Beautiful space for family vacation, girls getaways

MFL 2 West

3 bedrooms·2 baths

Chicago • Illinois

4.95(206 reviews)

$2,883.29 USD $2,450.81 USD total for 3 nights

Nov 6 – 9, 2026

Spacious open 4 bedroom vacation rental loft

Brick & timber loft with full hight walls for privacy

MFL 2 East

4 bedrooms·3 baths

Chicago • Illinois

4.93(120 reviews)

$2,186.67 USD $1,889.69 USD total for 3 nights

Nov 3 – 6, 2026

Fab space for the whole group!

Fully stocked chef's kitchen

MFL 3 East

4 bedrooms·4 baths

Chicago • Illinois

4.99(93 reviews)

$2,841.00 USD $2,445.91 USD total for 3 nights

Nov 3 – 6, 2026

Master Bedroom 2nd floor

1500Main EVANSTON

1500Main EVANSTON

2 bedrooms·1½ baths

Evanston • Illinois

5(166 reviews)

$1,140.42 USD total for 4 nights

Nov 16 – 20, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

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

$1,647.58 USD total for 3 nights

Nov 3 – 6, 2026

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

3 bedrooms·3 baths

Chicago • Illinois

$2,090.00 USD total for 5 nights

Nov 3 – 8, 2026

★ "This Airbnb is a gem! I’d highly recommend this spot—100%!"

LUXE Vintage Green Loft 10min to Downtown, Beach

[Bedroom #2] Queen bed, workspace & baby play pen

LUXE Vintage Green Loft 10min to Downtown, Beach

[Bedroom #1] King bed, stocked mini fridge & baby crib

LUXE Vintage Green Loft 10min to Downtown, Beach

3 bedrooms·3 baths

Chicago • Illinois

$1,095.00 USD total for 3 nights

Nov 3 – 6, 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)

$1,491.00 USD total for 3 nights

Nov 19 – 22, 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

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

1 bedroom·2 baths

Chicago • Illinois

$415.86 USD total for 3 nights

Nov 3 – 6, 2026

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

1 bedroom·2 baths

Chicago • Illinois

$556.60 USD total for 3 nights

Nov 3 – 6, 2026

Work, Explore, Rest | Ideal for Solo Guests

Work, Explore, Rest | Ideal for Solo Guests

Work, Explore, Rest | Ideal for Solo Guests

Work, Explore, Rest | Ideal for Solo Guests

Work, Explore, Rest | Ideal for Solo Guests

Work, Explore, Rest | Ideal for Solo Guests

1 bedroom·2 baths

Chicago • Illinois

$7,496.55 USD total for 3 nights

Aug 28 – 31, 2027

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027