Location

Dates

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Vacation rentals in Chicago

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

Oct 20 – 25, 2026

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

$620.46 USD total for 3 nights

Oct 20 – 23, 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

$471.39 USD total for 3 nights

Oct 20 – 23, 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

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

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

Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

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

All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

1 bedroom·2 baths

Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

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)

$2,378.69 USD $2,051.49 USD total for 3 nights

Oct 25 – 28, 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)

$3,104.93 USD $2,668.80 USD total for 3 nights

Oct 20 – 23, 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)

$2,307.68 USD $1,991.16 USD total for 3 nights

Nov 6 – 9, 2026

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

$718.13 USD total for 3 nights

Oct 20 – 23, 2026

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

$1,868.66 USD total for 3 nights

Oct 20 – 23, 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

$1,763.00 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – Nov 19, 2026

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

3 bedrooms·2 baths

Chicago • Illinois

$2,062.00 USD total for 3 nights

Oct 20 – 23, 2026

Fort Washington Railway Room, King Bed, Sofa Bed

Fort Washington Railway Room, King Bed, Sofa Bed

Fort Washington Railway Room, King Bed, Sofa Bed

Fort Washington Railway Room, King Bed, Sofa Bed

Fort Washington Railway Room, King Bed, Sofa Bed

Fort Washington Railway Room, King Bed, Sofa Bed

1 bedroom·2½ baths

Chicago • Illinois

$156.00 USD total for 3 nights

Oct 20 – 23, 2026