Vacation rentals in Streeterville, IL

74 available vacation rental offers

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Best vacation rentals and Airbnb offers in Streeterville, IL

Beautiful Home Near Downtwon - Free Parking! - Streeterville, IL

Beautiful Home Near Downtwon - Free Parking!

Homestay, Streeterville

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

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About Beautiful Home Near Downtwon - Free Parking!

Beautiful Home Near Downtwon - Free Parking! is a homestay in Streeterville, 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! - Streeterville, IL

Amazing Place to stay near Downtown Chicago!

Homestay, Streeterville

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

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About Amazing Place to stay near Downtown Chicago!

Amazing Place to stay near Downtown Chicago! is a homestay in Streeterville, 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 - Streeterville, IL

Scott House in Woodlawn - Basement

Apartment, Streeterville

Scott House in Woodlawn - Basement is a apartment in Streeterville. 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 Streeterville. 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 - Streeterville, IL

Hyde Park Shared Apartments

Apartment, Streeterville

Hyde Park Shared Apartments is a apartment in Streeterville. 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 Streeterville. 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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Vacation rentals with parking in Streeterville, IL

Find vacation rentals that make arriving by car easier.

Walk to Train l Near attractions and ORD l Free Parking l Patio - Streeterville, IL

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

Apartment, Streeterville

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

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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 Streeterville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,692.

From$178/night
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Cozy 2 Bedroom Home Near Downtown & Wrigley Field - Streeterville, IL

Cozy 2 Bedroom Home Near Downtown & Wrigley Field

Holiday Home, Streeterville

Cozy 2 Bedroom Home Near Downtown & Wrigley Field is a holiday home in Streeterville, 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 Streeterville, 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 $1,366.

From$195/night
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Comfortable and Trendy Design 1BR in Lincoln Square - Streeterville, IL

Comfortable and Trendy Design 1BR in Lincoln Square

Apartment, Streeterville

Comfortable and Trendy Design 1BR in Lincoln Square is a apartment in Streeterville, 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 Streeterville, 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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Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop - Streeterville, IL

Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop

Apartment, Streeterville

Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop is a apartment in Streeterville, with parking. This stay gives travelers a comfortable base for exploring the…

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About Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop

Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop is a apartment in Streeterville, 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 cancellation, free wifi, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,290.

From$327/night
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Pet-friendly vacation rentals in Streeterville, IL

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

Elegant Style Loft Montrose|13 mins DT|4 mins Lake - Streeterville, IL

Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Apartment, Streeterville

Elegant Style Loft Montrose · 13 mins DT · 4 mins Lake is a apartment in Streeterville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose · 13 mins DT · 4 mins Lake is a apartment in Streeterville, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,347.

From$192/night
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Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake - Streeterville, IL

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Apartment, Streeterville

Peaceful Cozy Beach View · 13 mins DT · 4 mins Lake is a apartment in Streeterville, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View · 13 mins DT · 4 mins Lake is a apartment in Streeterville, with pet-friendly space, easy beach access, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,365.

From$195/night
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2BR Fitness Pad • Private Gym • Sleeps 7 - Streeterville, IL

2BR Fitness Pad • Private Gym • Sleeps 7

Apartment, Streeterville

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in Streeterville, 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 Streeterville, 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 - Streeterville, IL

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Apartment, Streeterville

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood is a apartment in Streeterville, 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 Streeterville, 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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Vacation rentals with a kitchen in Streeterville, IL

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

Cozy and Intimate 1BR in Lively Lincoln Square - Streeterville, IL

Cozy and Intimate 1BR in Lively Lincoln Square

Apartment, Streeterville

Cozy and Intimate 1BR in Lively Lincoln Square is a apartment in Streeterville, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy and Intimate 1BR in Lively Lincoln Square

Cozy and Intimate 1BR in Lively Lincoln Square is a apartment in Streeterville, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,513.

From$216/night
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Luxury Villa 10 minutes to Downtown - Streeterville, IL

Luxury Villa 10 minutes to Downtown

Apartment, Streeterville

Luxury Villa 10 minutes to Downtown is a apartment in Streeterville, 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 Streeterville, 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 $1,520.

From$217/night
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Sleeps 7 • Huge Projector • Designated Workspace - Streeterville, IL

Sleeps 7 • Huge Projector • Designated Workspace

Apartment, Streeterville

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

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About Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 · Huge Projector · Designated Workspace is a apartment in Streeterville, 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 $1,548.

From$221/night
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Bridgeport Place -free parking, McCormick-Sox Park - Streeterville, IL

Bridgeport Place -free parking, McCormick-Sox Park

Apartment, Streeterville

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in Streeterville, 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 Streeterville, 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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Family-friendly vacation rentals in Streeterville, 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 - Streeterville, IL

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

Holiday Home, Streeterville

Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras is a holiday home in Streeterville, 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 Streeterville, 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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The Chic Urban Oasis Near the Lake! - Streeterville, IL

The Chic Urban Oasis Near the Lake!

Condo, Streeterville

The Chic Urban Oasis Near the Lake! is a condo in Streeterville, 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 Streeterville, 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 $1,533.

From$219/night
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Chicago Getaway: Family-Friendly 2BD 2BA Apartment - Streeterville, IL

Chicago Getaway: Family-Friendly 2BD 2BA Apartment

Apartment, Streeterville

Chicago Getaway: Family-Friendly 2BD 2BA Apartment is a apartment in Streeterville, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Chicago Getaway: Family-Friendly 2BD 2BA Apartment

Chicago Getaway: Family-Friendly 2BD 2BA Apartment is a apartment in Streeterville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,448.

From$350/night
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The Polo Inn Bridgeport U.S.A. - Streeterville, IL

The Polo Inn Bridgeport U.S.A.

B & B, Streeterville

The Polo Inn Bridgeport U.S.A. is a b & b in Streeterville, 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 Streeterville, 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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