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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

Nov 6 – 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

$465.22 USD total for 3 nights

Nov 6 – 9, 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

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)

$2,113.34 USD $1,827.39 USD total for 3 nights

Nov 9 – 12, 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)

$3,175.10 USD $2,729.89 USD total for 3 nights

Nov 6 – 9, 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)

$2,662.02 USD $2,262.71 USD total for 3 nights

Nov 16 – 19, 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

$4,040.74 USD total for 3 nights

Nov 6 – 9, 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

Nov 6 – Dec 6, 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

$2,411.00 USD total for 3 nights

Nov 6 – 9, 2026

Bright and inviting living room with a spacious sectional sofa, perfect for relaxing after a day of exploring Chicago. Floor-to-ceiling mirrored walls create an open, airy feel, while large windows fill the space with natural light.

3BR Vintage Apt • Back Yard• Walk to McKinley Park image 2

3BR Vintage Apt • Back Yard• Walk to McKinley Park image 3

Hand-painted vine and fruit mural along the upper wall near the ceiling, adding a distinctive decorative accent to the space.

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3 bedrooms·1 bath

Chicago • Illinois

4.92(25 reviews)

$646.25 USD total for 3 nights

Nov 8 – 11, 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

$2,342.00 USD total for 3 nights

Nov 6 – 9, 2026

Chicago Getaway | Cozy 2BR Near Downtown

Thoughtful extras: coffee bar, games, full cookware & pet-friendly perks

Chicago Getaway | Cozy 2BR Near Downtown

Chicago Getaway | Cozy 2BR Near Downtown

Bright living space with hardwood floors and wall-mounted streaming TV

Chicago Getaway | Cozy 2BR Near Downtown

2 bedrooms·1 bath

Chicago • Illinois

$79 – $796/ night(excl. fees & taxes)

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

$3,072.70 USD total for 31 nights

Nov 6 – Dec 7, 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

$2,913.05 USD total for 31 nights

Nov 6 – Dec 7, 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

$2,931.05 USD total for 31 nights

Dec 8, 2026 – Jan 8, 2027

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

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)

$492.26 USD total for 3 nights

Nov 6 – 9, 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

$897.29 USD total for 3 nights

Nov 6 – 9, 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

$779.69 USD total for 3 nights

Nov 6 – 9, 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

$959.62 USD total for 3 nights

Nov 6 – 9, 2026

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)

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)

$1,465.00 USD total for 3 nights

Nov 6 – 9, 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

$1,214.01 USD total for 3 nights

Nov 6 – 9, 2026