Vacation rentals in South Loop, IL

85 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best Vacation rentals and Airbnb offers in South Loop, IL

Scott House in Woodlawn - Basement - South Loop, IL

Scott House in Woodlawn - Basement

Apartment, South Loop

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

Read more

About Scott House in Woodlawn - Basement

Scott House in Woodlawn - Basement is a apartment in South Loop. 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 $659.

From$53/night
Show
Beautiful Home Near Downtwon - Free Parking! - South Loop, IL

Beautiful Home Near Downtwon - Free Parking!

Homestay, South Loop

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

Read more

About Beautiful Home Near Downtwon - Free Parking!

Beautiful Home Near Downtwon - Free Parking! is a homestay in South Loop, 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
Show
Amazing Place to stay near Downtown Chicago! - South Loop, IL

Amazing Place to stay near Downtown Chicago!

Homestay, South Loop

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

Read more

About Amazing Place to stay near Downtown Chicago!

Amazing Place to stay near Downtown Chicago! is a homestay in South Loop, 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
Show
Hyde Park Shared Apartments - South Loop, IL

Hyde Park Shared Apartments

Apartment, South Loop

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

Read more

About Hyde Park Shared Apartments

Hyde Park Shared Apartments is a apartment in South Loop. 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
Show

Best South Loop, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 - South Loop, IL

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

Apartment, South Loop

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

Read more

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 South Loop, 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 $1,736.

From$185/night
Show
Modern & Spacious Stay in Historic Bronzeville - South Loop, IL

Modern & Spacious Stay in Historic Bronzeville

Apartment, South Loop

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

Read more

About Modern & Spacious Stay in Historic Bronzeville

Modern & Spacious Stay in Historic Bronzeville is a apartment in South Loop, 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 $1,987.

From$203/night
Show
Bridgeport Place -free parking, McCormick-Sox Park - South Loop, IL

Bridgeport Place -free parking, McCormick-Sox Park

Apartment, South Loop

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

Read more

About Bridgeport Place -free parking, McCormick-Sox Park

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in South Loop, 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 $2,064.

From$216/night
Show
South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field - South Loop, IL

South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field

Apartment, South Loop

South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field is a apartment in South Loop, with pet-friendly space, parking, and…

Read more

About South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field

South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field is a apartment in South Loop, 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, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,921.

From$338/night
Show

Best Pet-Friendly Vacation Rentals in South Loop, IL

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

Private Workspace • Sleeps4 • Modern Stylish Stay - South Loop, IL

Private Workspace • Sleeps4 • Modern Stylish Stay

Apartment, South Loop

Private Workspace · Sleeps4 · Modern Stylish Stay is a apartment in South Loop, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

Read more

About Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace · Sleeps4 · Modern Stylish Stay is a apartment in South Loop, 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 $1,282.

From$118/night
Show
2BR Fitness Pad • Private Gym • Sleeps 7 - South Loop, IL

2BR Fitness Pad • Private Gym • Sleeps 7

Apartment, South Loop

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

Read more

About 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in South Loop, 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 $1,716.

From$165/night
Show
McCormick Place Beautiful Studio Suite with Optional Parking and Gym Access Sleeps 4 Near Soldier Field and Downtown Chicago - South Loop, IL

McCormick Place Beautiful Studio Suite with Optional Parking and Gym Access Sleeps 4 Near Soldier Field and Downtown Chicago

Apartment, South Loop

McCormick Place Beautiful Studio Suite with Optional Parking and Gym Access Sleeps 4 Near Soldier Field and Downtown Chicago is a apartment in South Loop, with pet-friendly space, parking,…

Read more

About McCormick Place Beautiful Studio Suite with Optional Parking and Gym Access Sleeps 4 Near Soldier Field and Downtown Chicago

McCormick Place Beautiful Studio Suite with Optional Parking and Gym Access Sleeps 4 Near Soldier Field and Downtown Chicago is a apartment in South Loop, 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, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,489.

From$290/night
Show
McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park - South Loop, IL

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park

Apartment, South Loop

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park is a apartment in South Loop, with pet-friendly space, parking, and room for a…

Read more

About McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park is a apartment in South Loop, 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, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,732.

From$315/night
Show

Best South Loop, IL vacation rentals with a kitchen

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

Bright/Cozy/Hip 2/1 Apt | Logan Square - South Loop, IL

Bright/Cozy/Hip 2/1 Apt | Logan Square

Apartment, South Loop

Bright/Cozy/Hip 2/1 Apt · Logan Square is a apartment in South Loop, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Bright/Cozy/Hip 2/1 Apt | Logan Square

Bright/Cozy/Hip 2/1 Apt · Logan Square is a apartment in South Loop, 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: kitchen, with kitchen, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,664.

From$145/night
Show
McCormick Oasis with Balcony, Patio and Gym Near Soldier Field & Museum Campus - South Loop, IL

McCormick Oasis with Balcony, Patio and Gym Near Soldier Field & Museum Campus

Apartment, South Loop

McCormick Oasis with Balcony, Patio and Gym Near Soldier Field & Museum Campus is a apartment in South Loop, with outdoor space and kitchen access. This stay gives travelers a comfortable…

Read more

About McCormick Oasis with Balcony, Patio and Gym Near Soldier Field & Museum Campus

McCormick Oasis with Balcony, Patio and Gym Near Soldier Field & Museum Campus is a apartment in South Loop, with outdoor 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,690.

From$270/night
Show
Premium 2BR Michigan Suite with Skyline Views Near McCormick Place & Lakefront - South Loop, IL

Premium 2BR Michigan Suite with Skyline Views Near McCormick Place & Lakefront

Apartment, South Loop

Premium 2BR Michigan Suite with Skyline Views Near McCormick Place & Lakefront is a apartment in South Loop, with kitchen access and room for a group. This stay gives travelers a…

Read more

About Premium 2BR Michigan Suite with Skyline Views Near McCormick Place & Lakefront

Premium 2BR Michigan Suite with Skyline Views Near McCormick Place & Lakefront is a apartment in South Loop, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,770.

From$275/night
Show
McCormick 2BR with Skyline View Near Soldier Field & Museum Campus - South Loop, IL

McCormick 2BR with Skyline View Near Soldier Field & Museum Campus

Apartment, South Loop

McCormick 2BR with Skyline View Near Soldier Field & Museum Campus is a apartment in South Loop, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

Read more

About McCormick 2BR with Skyline View Near Soldier Field & Museum Campus

McCormick 2BR with Skyline View Near Soldier Field & Museum Campus is a apartment in South Loop, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,835.

From$282/night
Show

Our Favorite Family-Friendly Vacation Rentals in South Loop, IL

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

Scott House in Woodlawn - Entire Building - includes basement space - South Loop, IL

Scott House in Woodlawn - Entire Building - includes basement space

Holiday Home, South Loop

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

Read more

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

Scott House in Woodlawn - Entire Building - includes basement space is a holiday home in South Loop, 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 $1,438.

From$142/night
Show
Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field - South Loop, IL

Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field

Apartment, South Loop

Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field is a apartment in South Loop, with kitchen access and room for a group. This stay gives travelers a comfortable base…

Read more

About Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field

Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field is a apartment in South Loop, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,567.

From$257/night
Show
Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums - South Loop, IL

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums

Apartment, South Loop

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums is a apartment in South Loop, with kitchen access and room for a group. This stay gives travelers a comfortable base…

Read more

About Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums is a apartment in South Loop, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,656.

From$267/night
Show
McCormick 2BR Family Retreat Near Museum Campus & Soldier Field - South Loop, IL

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field

Apartment, South Loop

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field is a apartment in South Loop, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About McCormick 2BR Family Retreat Near Museum Campus & Soldier Field

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field is a apartment in South Loop, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,959.

From$289/night
Show