Location

Dates

Guests

Vacation rentals in Darien, Illinois, United States

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

$ 2.036,80 USD totaal voor 3 nachten

15–18 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

$ 1.251,00 USD totaal voor 3 nachten

15–18 nov 2026

6 bedroom! Pool Table, Gaming Area, Firepit & More image 1

6 bedroom! Pool Table, Gaming Area, Firepit & More image 2

6 bedroom! Pool Table, Gaming Area, Firepit & More image 3

6 bedroom! Pool Table, Gaming Area, Firepit & More image 4

6 bedroom! Pool Table, Gaming Area, Firepit & More image 5

6 bedroom! Pool Table, Gaming Area, Firepit & More

6 bedrooms·3 baths

Joliet • Illinois

4.92(24 reviews)

$ 2.440,00 USD totaal voor 3 nachten

15–18 nov 2026

The Pilsen Hideaway | Cozy Private Room

The Pilsen Hideaway | Cozy Private Room

The Pilsen Hideaway | Cozy Private Room

The Pilsen Hideaway | Cozy Private Room

The Pilsen Hideaway | Cozy Private Room

The Pilsen Hideaway | Cozy Private Room

1 bedroom·1 bath

Chicago • Illinois

$ 247,00 USD totaal voor 3 nachten

15–18 nov 2026

Chicago Townhome with Roof Deck image 1

Chicago Townhome with Roof Deck image 2

Chicago Townhome with Roof Deck image 3

Chicago Townhome with Roof Deck image 4

Chicago Townhome with Roof Deck image 5

Chicago Townhome with Roof Deck

3 bedrooms·3 baths

Chicago • Illinois

5(43 reviews)

$ 840,00 USD totaal voor 3 nachten

15–18 nov 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

$ 1.104,00 USD totaal voor 3 nachten

15–18 nov 2026

Blue Oasis

2 bedrooms·1 bath

Chicago • Illinois

$ 633,07 USD totaal voor 3 nachten

16–19 dec 2026

Large Cozy 3BR near UChicago Medical Midway Museum

Main bedroom from desk area

Second bedroom -- a headboard has been added (didn't get a picture of that yet).

Third bedroom, desk and closet

Large Cozy 3BR near UChicago Medical Midway Museum

3 bedrooms·1 bath

Chicago • Illinois

5(8 reviews)

$349/ nacht(excl. kosten & belastingen)

Hyde Park 2BR UChicago Medical Museums 20% OFF

Hyde Park 2BR UChicago Medical Museums 20% OFF

Hyde Park 2BR UChicago Medical Museums 20% OFF

Quick view of upstairs "half kitchen," middle of tile restoral.
NOTE there is a microwave and induction burner, NO STOVE.

Hyde Park 2BR UChicago Medical Museums 20% OFF

2 bedrooms·1 bath

Chicago • Illinois

5(4 reviews)

$233/ nacht(excl. kosten & belastingen)

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

2 bedrooms·2 baths

Chicago • Illinois

$ 4.170,00 USD totaal voor 30 nachten

15 nov – 15 dec 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

$ 578,05 USD totaal voor 3 nachten

15–18 nov 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)

$ 1.013,00 USD totaal voor 3 nachten

18–21 nov 2026

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

2 bedrooms·1 bath

Chicago • Illinois

$ 572,71 USD totaal voor 3 nachten

15–18 nov 2026

Sleeps 4 • Stylish Stay with Workspace

Sleeps 4 • Stylish Stay with Workspace

Sleeps 4 • Stylish Stay with Workspace

Sleeps 4 • Stylish Stay with Workspace

Sleeps 4 • Stylish Stay with Workspace

Sleeps 4 • Stylish Stay with Workspace

1 bedroom·1 bath

Chicago • Illinois

$ 497,45 USD totaal voor 3 nachten

15–18 nov 2026

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

1 bedroom·1 bath

Chicago • Illinois

$ 479,81 USD totaal voor 3 nachten

15–18 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

$ 399,82 USD totaal voor 3 nachten

15–18 nov 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

$ 501,25 USD totaal voor 3 nachten

15–18 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

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

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 totaal voor 3 nachten

28–31 aug 2027

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

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 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

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 totaal voor 3 nachten

28–31 aug 2027