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 totaal voor 31 nachten

3 nov – 4 dec 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 totaal voor 31 nachten

26 jan – 26 feb 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 totaal voor 31 nachten

8 dec 2026 – 8 jan 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 totaal voor 3 nachten

3–6 nov 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 totaal voor 3 nachten

9–12 nov 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 totaal voor 3 nachten

3–6 nov 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 totaal voor 3 nachten

4–7 nov 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 totaal voor 3 nachten

3–6 nov 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
MFL 2 West

MFL 2 West

3 bedrooms·2 baths
Chicago • Illinois
4.95(206 reviews)

$ 2.883,29 USD $ 2.450,81 USD totaal voor 3 nachten

6–9 nov 2026

Spacious open 4 bedroom vacation rental loft
MFL 2 East
MFL 2 East
Skyline views
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 totaal voor 3 nachten

3–6 nov 2026

Fab space for the whole group!
MFL 3 East
Fully stocked chef's kitchen
MFL 3 East
MFL 3 East

MFL 3 East

4 bedrooms·4 baths
Chicago • Illinois
4.99(93 reviews)

$ 2.841,00 USD $ 2.445,91 USD totaal voor 3 nachten

3–6 nov 2026

Main Floor
Master Bedroom 2nd floor
Dining area
1500Main EVANSTON
Main Floor

1500Main EVANSTON

2 bedrooms·1½ baths
Evanston • Illinois
5(166 reviews)

$ 1.140,42 USD totaal voor 4 nachten

16–20 nov 2026

Ashland
Living room
Workspace in the living room
Bedroom 1
Bedroom 2

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 totaal voor 3 nachten

3–6 nov 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 totaal voor 5 nachten

3–8 nov 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 totaal voor 3 nachten

3–6 nov 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 totaal voor 3 nachten

19–22 nov 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 totaal voor 3 nachten

8–11 nov 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 totaal voor 3 nachten

3–6 nov 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 totaal voor 3 nachten

28–31 aug 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 totaal voor 3 nachten

3–6 nov 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 totaal voor 3 nachten

28–31 aug 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 totaal voor 3 nachten

28–31 aug 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 totaal voor 3 nachten

28–31 aug 2027