Vacation rentals in Chicago, IL

Best vacation rentals and Airbnb offers in Chicago, IL

Beautiful Home Near Downtwon - Free Parking!

Homestay, Chicago

Beautiful Home Near Downtwon - Free Parking! is a homestay in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Beautiful Home Near Downtwon - Free Parking!

Beautiful Home Near Downtwon - Free Parking! is a homestay in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $501.

From$60/night

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Amazing Place to stay near Downtown Chicago!

Homestay, Chicago

Amazing Place to stay near Downtown Chicago! is a homestay in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Amazing Place to stay near Downtown Chicago!

Amazing Place to stay near Downtown Chicago! is a homestay in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $628.

From$75/night

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Scott House in Woodlawn - Basement

Apartment, Chicago

Scott House in Woodlawn - Basement is a apartment in Chicago. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Scott House in Woodlawn - Basement

Scott House in Woodlawn - Basement is a apartment in Chicago. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, and tv.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $537.

From$77/night

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Hyde Park Shared Apartments

Apartment, Chicago

Hyde Park Shared Apartments is a apartment in Chicago. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Hyde Park Shared Apartments

Hyde Park Shared Apartments is a apartment in Chicago. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, washer, and dryer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $847.

From$101/night

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Family-friendly vacation rentals in Chicago, IL

Plan a trip with stays that give families more room to spread out.

Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras

Holiday Home, Chicago

Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras is a holiday home in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras

Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras is a holiday home in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,105.

From$158/night

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Scott House in Woodlawn - Entire Building - includes basement space

Holiday Home, Chicago

Scott House in Woodlawn - Entire Building - includes basement space is a holiday home in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Scott House in Woodlawn - Entire Building - includes basement space

Scott House in Woodlawn - Entire Building - includes basement space is a holiday home in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,166.

From$167/night

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The Chic Urban Oasis Near the Lake!

Condo, Chicago

The Chic Urban Oasis Near the Lake! is a condo in Chicago, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Chic Urban Oasis Near the Lake!

The Chic Urban Oasis Near the Lake! is a condo in Chicago, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,552.

From$222/night

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The Polo Inn Bridgeport U.S.A.

B & B, Chicago

The Polo Inn Bridgeport U.S.A. is a b & b in Chicago, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About The Polo Inn Bridgeport U.S.A.

The Polo Inn Bridgeport U.S.A. is a b & b in Chicago, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, kids friendly, kids meal, parking, and paid parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,845.

From$360/night

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Pet-friendly vacation rentals in Chicago, IL

Bring your pet along with stays that welcome four-legged travelers.

Sunny, Spacious, 3BR 1BA Davlin INN Chicago

Apartment, Chicago

Sunny, Spacious, 3BR 1BA Davlin INN Chicago is a apartment in Chicago, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Sunny, Spacious, 3BR 1BA Davlin INN Chicago

Sunny, Spacious, 3BR 1BA Davlin INN Chicago is a apartment in Chicago, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,415.

From$358/night

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2BR Fitness Pad • Private Gym • Sleeps 7

Apartment, Chicago

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in Chicago, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in Chicago, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,460.

From$209/night

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Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Apartment, Chicago

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood is a apartment in Chicago, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood is a apartment in Chicago, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,533.

From$219/night

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Mich Ave Downtown Penthouse - Rooftop+Gym

Condo, Chicago

Mich Ave Downtown Penthouse - Rooftop+Gym is a condo in Chicago, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mich Ave Downtown Penthouse - Rooftop+Gym

Mich Ave Downtown Penthouse - Rooftop+Gym is a condo in Chicago, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,217.

From$460/night

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Vacation rentals with parking in Chicago, IL

Find vacation rentals that make arriving by car easier.

Kenwood Apartments, Downtown Hyde Park

Homestay, Chicago

Kenwood Apartments, Downtown Hyde Park is a homestay in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Kenwood Apartments, Downtown Hyde Park

Kenwood Apartments, Downtown Hyde Park is a homestay in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $935.

From$134/night

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Walk to Train l Near attractions and ORD l Free Parking l Patio

Apartment, Chicago

Walk to Train l Near attractions and ORD l Free Parking l Patio is a apartment in Chicago, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the…

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About Walk to Train l Near attractions and ORD l Free Parking l Patio

Walk to Train l Near attractions and ORD l Free Parking l Patio is a apartment in Chicago, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,692.

From$178/night

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Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Apartment, Chicago

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT is a apartment in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT is a apartment in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,269.

From$181/night

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Luxury Villa 10 minutes to Downtown

Apartment, Chicago

Luxury Villa 10 minutes to Downtown is a apartment in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury Villa 10 minutes to Downtown

Luxury Villa 10 minutes to Downtown is a apartment in Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,520.

From$217/night

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Vacation rentals with a kitchen in Chicago, IL

Compare stays with kitchen access for longer trips and easier meals.

Modern Garden Apartment w/ New Kitchen + Bathroom

Apartment, Chicago

Modern Garden Apartment w/ New Kitchen + Bathroom is a apartment in Chicago, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Modern Garden Apartment w/ New Kitchen + Bathroom

Modern Garden Apartment w/ New Kitchen + Bathroom is a apartment in Chicago, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,312.

From$187/night

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Bridgeport Place -free parking, McCormick-Sox Park

Apartment, Chicago

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in Chicago, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Bridgeport Place -free parking, McCormick-Sox Park

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in Chicago, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,741.

From$249/night

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LIVN Millennium Park Downtown Chicago Superior 1BR

Apartment, Chicago

LIVN Millennium Park Downtown Chicago Superior 1BR is a apartment in Chicago, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR is a apartment in Chicago, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,456.

From$351/night

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LIVN Millennium Park Downtown Chicago 1 BR

Apartment, Chicago

LIVN Millennium Park Downtown Chicago 1 BR is a apartment in Chicago, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR is a apartment in Chicago, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,530.

From$361/night

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