Vacation Rental Homes, Apartments & Condos for Rent in Chicago, Illinois

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• Bedrooms
  • 1 bedroom (8)
  • 2 bedrooms (9)
  • 3 bedrooms (9)
  • 4+ bedrooms (6)

• Sleeps
  • Sleeps 1-4 (12)
  • Sleeps 5-8 (14)
  • Sleeps 9-12 (5)
  • Sleeps 13 or more (1)

• Bathrooms
  • 1 bathroom (15)
  • 2 bathrooms (10)
  • 3 bathrooms (4)
  • 4+ bathrooms (3)

• Property Type
  • apartment rentals (10)
  • condo rentals (13)
  • house rentals (7)
  • townhome rentals (1)

• Accessibility
  • long term renters welcome (17)
  • non smoking only (23)
  • pet friendly (2)
  • wheelchair accessible (4)

• Location Type
  • beach rentals (2)
  • lake rentals (22)
  • river rentals (2)

• Travel Style
  • budget rentals (2)
  • luxury rentals (13)

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Classic 3 Bedroom Victorian Greystone in Chicago's Wrigleyville!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 170782

3 Bedrooms, Sleeps 5

• Apartment
• 1 Bathroom
• downtown, lake
• accept credit card

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Rates per property (USD)

$1,820/week

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Beautiful 3 Bedroom South Loop TH w/ yard, easy parking, cable and Internet

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 169185

3 Bedrooms, Sleeps 8

• Townhome
• 3 Bathrooms
• downtown, lake
• air-conditioning

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Rates per property (USD)

$300 - $400/night

$2,000/week

$6,000/month

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Chicago Guest House on Lakewood 'Wrigleyville'

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 319468

3 Bedrooms, Sleeps 6

• Apartment
• 2 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$380/night

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Chicago Guest House-Nowhere Will You Feel More At Home!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 116901

3 Bedrooms, Sleeps 6

• House
• 3 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$425/night

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Chicago Guest House-Wrigley Suite 'Wrigleyville'

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 319203

4 Bedrooms, Sleeps 8

• Apartment
• 2 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$495/night

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Chicago Guest House-Lakeview Suite 'Wrigleyville'

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 153025

3 Bedrooms, Sleeps 6

• Condo
• 2 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$380/night

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Chicago Guest House -Clark Suite 'Wrigleyville'

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 146193

3 Bedrooms, Sleeps 8

• Apartment
• 2 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$450/night

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Affordable Luxury w/Stunning Skyline/River Views, Perfect Location w/Parking!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 184807

2 Bedrooms, Sleeps 6

• Condo
• 2 Bathrooms
• downtown, river
• accept credit card

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Rates per property (USD)

$249 - $299/night

$1,494 - $1,794/week

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Historical Loft Building - Great Downtown Location

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 203371

1 Bedroom, Sleeps 4

• Condo
• 1 Bathroom
• downtown, lake
• air-conditioning

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Magnificent Mile , Gold Coast Luxury Brownstone Downtown!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 188897

2 Bedrooms, Sleeps 6

• Apartment
• 2 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$275 - $400/night

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The Chicago Guest House Belmont Suite in Lakeview, Chicago

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 320912

2 Bedrooms, Sleeps 4

• Apartment
• 1 Bathroom
• downtown, lake

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Rates per property (USD)

$250/night

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Magnificent Mile 1BR - Next to Oprah's House and Lake MI

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 206014

1 Bedroom, Sleeps 4

• Condo
• 1 Bathroom
• downtown
• accept credit card

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WEEKLY SPECIALS OCT + NOV!! Goldcoast High-Rise 4-6 people

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 168042

2 Bedrooms, Sleeps 4

• Condo
• 1 Bathroom
• beach, downtown
• accept credit card

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Rates per property (USD)

$235 - $265/night

$1,650/week

$3,600 - $3,700/month

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New Downtown Condo!! Great Location!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 172675

1 Bedroom, Sleeps 4

• Condo
• 1 Bathroom
• downtown, lake
• accept credit card

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Rates per property (USD)

$249 - $269/night

$1,695/week

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Chicago's Best Location! 18th Floor, 1 Block to Mich Ave Shopping

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 204526

2 Bedrooms, Sleeps 6

• Condo
• 2 Bathrooms
• downtown
• accept credit card

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Rates per property (USD)

$249 - $299/night

$1,500/week

$5,500/month

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Condo in Downtown, Walk to Museums, Shopping, Restaurants, Close to Mccormick Pl

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 208026

1 Bedroom, Sleeps 4

• Condo
• 1 Bathroom
• beach, downtown
• accept credit card

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Rates per property (USD)

$150/night

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Luxury 1 bedroom apt in Chicago's Lincoln Park

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 173059

1 Bedroom, Sleeps 4

• Apartment
• 1 Bathroom
• downtown, lake
• accept credit card

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Rates per property (USD)

$130/night

$850/week

$2,000/month

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Awesome Loft, Walking Distance to Downtown & Nightlife

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 187962

2 Bedrooms, Sleeps 6

• Condo
• 2 Bathrooms
• downtown, lake
• accept credit card

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Rates per property (USD)

$200 - $280/night

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Fantastic Single Family Home in Old Town- Walking distance to Michigan Ave.

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 205648

5 Bedrooms, Sleeps 10

• House
• 3 Bathrooms, 1 Half Bath
• downtown, lake
• accept credit card

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Rates per property (USD)

$750/night

$5,000/week

$15,000/month

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December and January Rate Special! ~ Designer Chicago Apartment!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 163725

3 Bedrooms, Sleeps 8

• Apartment
• 1 Bathroom
• downtown, lake
• accept credit card

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Rates per property (USD)

$200 - $250/night

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Large Luxury Home near Downtown Chicago

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 169076

5 Bedrooms, Sleeps 15

• House
• 4 Bathrooms, 1 Half Bath
• downtown, river
• accept credit card

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Rates per property (USD)

$1,075/night

$5,500/week

$15,000/month

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Modern 4 Level Home. Minutes from Downtown

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 183649

4 Bedrooms, Sleeps 10

• House
• 3 Bathrooms, 1 Half Bath
• downtown, lake
• accept credit card

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Rates per property (USD)

$300 - $495/night

$2,700/week

$8,000/month

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Chicago Marathon Special

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 160572

3 Bedrooms, Sleeps 9

• Condo
• 1 Bathroom
• downtown
• accept credit card

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Rates per property (USD)

$215/night

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Luxury Furnished Suite in the heart of Downtown Chicago

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 158850

2 Bedrooms, Sleeps 4

• Apartment
• 1 Bathroom
• downtown, lake
• accept credit card

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The Wrigleyville Mansion - 3 Blocks from Wrigley Field

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 186943

5 Bedrooms, Sleeps 12

• House
• 5 Bathrooms
• downtown
• air-conditioning

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Heart of Chicago Fully Furnished w/Million $$$ views -

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 128129

1 Bedroom, Sleeps 2

• Condo
• 1 Bathroom
• downtown
• accept credit card

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Downtown Chicago Luxury Home - Elegance, Comfort, Convenience

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 154813

4 Bedrooms, Sleeps 11

• House
• 4 Bathrooms
• downtown, lake
• accept credit card

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Massive! 1800 Sq. Ft Corner unit Overlooking Lake Michigan, City and Navy Pier!

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 178126

3 Bedrooms, Sleeps 8

• Apartment
• 2 Bathrooms, 1 Half Bath
• downtown, lake
• accept credit card

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Rates per property (USD)

$399 - $425/night

$2,793/week

$9,500/month

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Millennium Park

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 144766

1 Bedroom, Sleeps 2

• Condo
• 1 Bathroom
• downtown, lake
• accept credit card

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Rates per property (USD)

$160 - $180/night

$2,800/month

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Biddle House #1

1. USA,
2. Illinois,
3. Chicago Vacation Rentals

— Property 174934

2 Bedrooms, Sleeps 6

• House
• 1 Bathroom
• downtown, lake
• accept credit card

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Rates per property (USD)

$225/night

$3,600/month

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