Location

Dates

Guests

Vacation rentals in Chicago

"Wine" Room - 1 block from train, Victorian Charm

"Wine" Room - 1 block from train, Victorian Charm

"Wine" Room - 1 block from train, Victorian Charm

"Wine" Room - 1 block from train, Victorian Charm

"Wine" Room - 1 block from train, Victorian Charm

"Wine" Room - 1 block from train, Victorian Charm

1 bedroom·2½ baths

Chicago • Illinois

$49 – $170/ night(excl. fees & taxes)

Green Room, Free Parking, King Bed, 1 Block to CTA

Green Room, Free Parking, King Bed, 1 Block to CTA

Green Room, Free Parking, King Bed, 1 Block to CTA

Green Room, Free Parking, King Bed, 1 Block to CTA

Green Room, Free Parking, King Bed, 1 Block to CTA

Green Room, Free Parking, King Bed, 1 Block to CTA

1 bedroom·2½ baths

Chicago • Illinois

$49 – $167/ night(excl. fees & taxes)

Celestial Room - 20 Min to Downtown, Free parking

Celestial Room - 20 Min to Downtown, Free parking

Celestial Room - 20 Min to Downtown, Free parking

Celestial Room - 20 Min to Downtown, Free parking

Celestial Room - 20 Min to Downtown, Free parking

Celestial Room - 20 Min to Downtown, Free parking

1 bedroom·2½ baths

Chicago • Illinois

$49 – $158/ night(excl. fees & taxes)

Teal Room - King Bed, near CTA, 20min to Downtown

Teal Room - King Bed, near CTA, 20min to Downtown

Teal Room - King Bed, near CTA, 20min to Downtown

Teal Room - King Bed, near CTA, 20min to Downtown

Teal Room - King Bed, near CTA, 20min to Downtown

Teal Room - King Bed, near CTA, 20min to Downtown

1 bedroom·2½ baths

Chicago • Illinois

$49 – $192/ night(excl. fees & taxes)

Garden Room - King Bed, Sofa Bed, 1 Block to Train

Garden Room - King Bed, Sofa Bed, 1 Block to Train

Garden Room - King Bed, Sofa Bed, 1 Block to Train

Garden Room - King Bed, Sofa Bed, 1 Block to Train

Garden Room - King Bed, Sofa Bed, 1 Block to Train

Garden Room - King Bed, Sofa Bed, 1 Block to Train

1 bedroom·2½ baths

Chicago • Illinois

$49 – $164/ night(excl. fees & taxes)

Vintage Airline - Close to Train, Full Size Bed

Vintage Airline - Close to Train, Full Size Bed

Vintage Airline - Close to Train, Full Size Bed

Vintage Airline - Close to Train, Full Size Bed

Vintage Airline - Close to Train, Full Size Bed

Vintage Airline - Close to Train, Full Size Bed

1 bedroom·2½ baths

Chicago • Illinois

$49 – $177/ night(excl. fees & taxes)

Egyptian Room - Free Parking, 1 block to CTA

Egyptian Room - Free Parking, 1 block to CTA

Egyptian Room - Free Parking, 1 block to CTA

Egyptian Room - Free Parking, 1 block to CTA

Egyptian Room - Free Parking, 1 block to CTA

Egyptian Room - Free Parking, 1 block to CTA

1 bedroom·2½ baths

Chicago • Illinois

$49 – $161/ night(excl. fees & taxes)

Cottage Crafts Room - Free Parking, 1 block to CTA

Cottage Crafts Room - Free Parking, 1 block to CTA

Cottage Crafts Room - Free Parking, 1 block to CTA

Cottage Crafts Room - Free Parking, 1 block to CTA

Cottage Crafts Room - Free Parking, 1 block to CTA

Cottage Crafts Room - Free Parking, 1 block to CTA

1 bedroom·2½ baths

Chicago • Illinois

$49 – $192/ night(excl. fees & taxes)

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

$244 – $1,598/ night(excl. fees & taxes)

★ "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

$231 – $1,595/ night(excl. fees & taxes)

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)

$622.12 USD total for 3 nights

Sep 22 – 25, 2026

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

$93 – $98/ night(excl. fees & taxes)

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

$88 – $93/ night(excl. fees & taxes)

Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

2 bedrooms·1 bath

Chicago • Illinois

4.75(24 reviews)

$767.00 USD total for 3 nights

Sep 22 – 25, 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

$53 – $1,000/ night(excl. fees & taxes)

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

$52 – $1,000/ night(excl. fees & taxes)

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

$61 – $1,000/ night(excl. fees & taxes)

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/ night(excl. fees & taxes)

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/ night(excl. fees & taxes)

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

7 bedrooms·3 baths

Chicago • Illinois

$338 – $3,000/ night(excl. fees & taxes)

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

5(92 reviews)

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

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

$82 – $3,000/ night(excl. fees & taxes)

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

$82 – $3,000/ night(excl. fees & taxes)

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

6 bedrooms·4 baths

Chicago • Illinois

$3,600.00 USD total for 3 nights

Sep 22 – 25, 2026