Vacation rentals in Downtown Chicago, IL

82 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Downtown Chicago, IL

Beautiful Home Near Downtwon - Free Parking! - Downtown Chicago, IL

Beautiful Home Near Downtwon - Free Parking!

Homestay, Downtown Chicago

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

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About Beautiful Home Near Downtwon - Free Parking!

Beautiful Home Near Downtwon - Free Parking! is a homestay in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $501.

From$60/night
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Amazing Place to stay near Downtown Chicago! - Downtown Chicago, IL

Amazing Place to stay near Downtown Chicago!

Homestay, Downtown Chicago

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

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About Amazing Place to stay near Downtown Chicago!

Amazing Place to stay near Downtown Chicago! is a homestay in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $628.

From$75/night
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Scott House in Woodlawn - Basement - Downtown Chicago, IL

Scott House in Woodlawn - Basement

Apartment, Downtown Chicago

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

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About Scott House in Woodlawn - Basement

Scott House in Woodlawn - Basement is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $537.

From$77/night
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Hyde Park Shared Apartments - Downtown Chicago, IL

Hyde Park Shared Apartments

Apartment, Downtown Chicago

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

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About Hyde Park Shared Apartments

Hyde Park Shared Apartments is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $847.

From$101/night
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Best Downtown Chicago, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Kenwood Apartments, Downtown Hyde Park - Downtown Chicago, IL

Kenwood Apartments, Downtown Hyde Park

Homestay, Downtown Chicago

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

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About Kenwood Apartments, Downtown Hyde Park

Kenwood Apartments, Downtown Hyde Park is a homestay in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $935.

From$134/night
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Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI - Downtown Chicago, IL

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Apartment, Downtown Chicago

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI is a apartment in Downtown Chicago, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,318.

From$188/night
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Cozy 2 Bedroom Home Near Downtown & Wrigley Field - Downtown Chicago, IL

Cozy 2 Bedroom Home Near Downtown & Wrigley Field

Holiday Home, Downtown Chicago

Cozy 2 Bedroom Home Near Downtown & Wrigley Field is a holiday home in Downtown Chicago, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 2 Bedroom Home Near Downtown & Wrigley Field

Cozy 2 Bedroom Home Near Downtown & Wrigley Field is a holiday home in Downtown Chicago, with parking, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,370.

From$196/night
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Comfortable and Trendy Design 1BR in Lincoln Square - Downtown Chicago, IL

Comfortable and Trendy Design 1BR in Lincoln Square

Apartment, Downtown Chicago

Comfortable and Trendy Design 1BR in Lincoln Square is a apartment in Downtown Chicago, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Comfortable and Trendy Design 1BR in Lincoln Square

Comfortable and Trendy Design 1BR in Lincoln Square is a apartment in Downtown Chicago, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,483.

From$212/night
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Best Pet-Friendly Vacation Rentals in Downtown Chicago, IL

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

Sunny, Spacious, 3BR 1BA Davlin INN Chicago - Downtown Chicago, IL

Sunny, Spacious, 3BR 1BA Davlin INN Chicago

Apartment, Downtown Chicago

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

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

Sunny, Spacious, 3BR 1BA Davlin INN Chicago is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,371.

From$352/night
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2BR Fitness Pad • Private Gym • Sleeps 7 - Downtown Chicago, IL

2BR Fitness Pad • Private Gym • Sleeps 7

Apartment, Downtown Chicago

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

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About 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,460.

From$209/night
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Retro 2 bedroom bungalow in Chicago's Avondale neighborhood - Downtown Chicago, IL

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Apartment, Downtown Chicago

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

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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 Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,533.

From$219/night
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Sleeps 7 • Huge Projector • Designated Workspace - Downtown Chicago, IL

Sleeps 7 • Huge Projector • Designated Workspace

Apartment, Downtown Chicago

Sleeps 7 · Huge Projector · Designated Workspace is a apartment in Downtown Chicago, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 · Huge Projector · Designated Workspace is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,545.

From$221/night
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Best Downtown Chicago, IL vacation rentals with a kitchen

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

Modern Garden Apartment w/ New Kitchen + Bathroom - Downtown Chicago, IL

Modern Garden Apartment w/ New Kitchen + Bathroom

Apartment, Downtown Chicago

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

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About Modern Garden Apartment w/ New Kitchen + Bathroom

Modern Garden Apartment w/ New Kitchen + Bathroom is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,316.

From$188/night
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Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 - Downtown Chicago, IL

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Apartment, Downtown Chicago

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 is a apartment in Downtown Chicago, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 is a apartment in Downtown 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,557.

From$222/night
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Modern & Spacious Stay in Historic Bronzeville - Downtown Chicago, IL

Modern & Spacious Stay in Historic Bronzeville

Apartment, Downtown Chicago

Modern & Spacious Stay in Historic Bronzeville is a apartment in Downtown Chicago, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Modern & Spacious Stay in Historic Bronzeville

Modern & Spacious Stay in Historic Bronzeville is a apartment in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,741.

From$249/night
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Bridgeport Place -free parking, McCormick-Sox Park - Downtown Chicago, IL

Bridgeport Place -free parking, McCormick-Sox Park

Apartment, Downtown Chicago

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in Downtown 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 Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,768.

From$253/night
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Our Favorite Family-Friendly Vacation Rentals in Downtown 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 - Downtown Chicago, IL

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

Holiday Home, Downtown Chicago

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

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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 Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,105.

From$158/night
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Scott House in Woodlawn - Entire Building - includes basement space - Downtown Chicago, IL

Scott House in Woodlawn - Entire Building - includes basement space

Holiday Home, Downtown Chicago

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

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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 Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$167/night
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The Chic Urban Oasis Near the Lake! - Downtown Chicago, IL

The Chic Urban Oasis Near the Lake!

Condo, Downtown Chicago

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

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About The Chic Urban Oasis Near the Lake!

The Chic Urban Oasis Near the Lake! is a condo in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,552.

From$222/night
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The Polo Inn Bridgeport U.S.A. - Downtown Chicago, IL

The Polo Inn Bridgeport U.S.A.

B & B, Downtown Chicago

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

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About The Polo Inn Bridgeport U.S.A.

The Polo Inn Bridgeport U.S.A. is a b & b in Downtown 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,845.

From$360/night
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Airbnb, vacation rentals and homes in Downtown Chicago | sillystay