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Vacation Rentals in Chicago, Illinois

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Chicago, Illinois Vacation Rentals and Tourism

It’s impossible to return home from a Chicago vacation without feeling a lot more enlightened and cultured. The world-famous city in Illinois has open arms for everybody, no matter their age, background, or lifestyle. So no matter who you are or where you're from, Chicago vacation rentals are right up your alley. 

If you want a lot on your plate when you vacation, Chicago rentals are your dream-come-true. The exquisite jazz and blues clubs will delight music lovers. Wrigley Field will thrill those who enjoy America’s favorite pastime, baseball. Kids (and their parents too) will lose track of time at the attraction-filled Navy Pier and Lincoln Park Zoo. Museum hoppers won’t ever run out of things to do, which will likely include a tour of the Art Institute of Chicago. And everybody will be intrigued by the many historical and architectural landmarks, like the famous Sears Tower. Don’t forget to spend at least one day in Millennium Park, which offers up adventure year-round (in the winter, you can ice skate). Also, Michigan Lake is always fun when it’s sunny out. Downtown Chicago vacation rentals will put you especially close to all the action.

If Chicago condo rentals don't sound appealing to you by now, then perhaps you’re concerned about how affordable your getaway will be! Fortunately, thanks to the many Chicago weekly rentals, studios for rent, and condos, found here, you can definitely find cheap accommodations. Whether it’s Chicago weekly rentals or short term rentals, Chicago makes it easy to save money. And in fact, although dining out in Chicago is an unforgettable experience in itself, you still have the option to save money and dine in because one of our Chicago luxury rentals, which will surely have a kitchen. You certainly can’t say the same for a hotel.

Vacation rentals in Chicago are extremely popular as they allow tourists to really enjoy the vibrant local culture of the city. Don’t hide away in a resort hotel; instead stay in one of the cozy Chicago condo rentals found here! There’s a reason people keep coming back to this rich and exciting city, so why don’t you experience it for yourself by booking one of the condos, downtown apartments, or studios for rent in Chicago, listed right here!

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more destinations

Check out more areas which feature homes, villas, cabins, cottages, or condos.

Chicago things to do

 

Puppet Bike

Puppet Bike, you are sunshine on a cloudy day. Humans and puppets, young and old are mesmerized by you. No matter when or where I see you, I have to stop...read more

 

The Art Institute of Chicago

This was a great place to go and cool down from the hot summer heat. There is absolutely no food allowed. My friend was carrying a trader joe's bag, and so...read more

 

Chicago Symphony Orchestra

Do not arrive late. Do not take photos. Do not sneeze, cough, or make any kind of noise during the performace. Honor this unspoken code & you will have a...read more

 

Millennium Park

Definitely a modern day park done right, it's the perfect integration of city meets nature if you ask me. The bean is great for selfies! But seriously its...read more

 

The Tamale Guy

We were going out, and we were all like 'I HOPE WE SEE THE TAMALE GUY TONIGHT, HE HAS THE BEST TAMALES!' And then the universe, in her all powerful and...read more

 

Museum Campus Chicago

It's a city of museums! Our local friends decided to take us to a popular destination to see the whole skyline of their beautiful city. The museum campus...read more

 

Buckingham Fountain

One of my oldest memories is visiting this fountain. Still beautiful and mesmerizing. I love it at night. The lights and music compliment the spouting...read more

 

The Cloud Gate aka the 'Bean'

Pure awesomeness...... Does it ever get rust?? Dont think so.... This indeed is a mandatory visit. Try to take some time to enjoy the surroundings and...read more

 

Tejas Yoga

One of the most amazing yoga experiences!! My friend and I got a groupon and thought we would try this place out based on its amazing reviews-boy does it...read more

 

Strike Your Resolutions Yelp Elite Event

How could it get any better? It can't! I shared a lane with some great yelpers and really enjoyed the social aspect of this event. The drinks were...read more

 

Rotofugi Designer Toy Store & Gallery

Whenever I'm in a bad mood, I head to Rotofugi. They have a million bazillion cute and fun things, as well as one of those plastic mold toy makers (the...read more

 

Chicago Architecture Foundation

Why did you charge me 22$ to bring my 18 month old on the boat? She didn't take up a seat or drink any booze. Interesting tour, terrible business model.read more

 

Lyric Opera of Chicago

This review is based on the outstanding performance of The Sound Of Music. Buying tickets, arriving via Metra, entering the amazing architecture, enjoying...read more

 

Robert Lekan Training

Oh Rob, where do I even begin!? If you're looking for an in-your-face, give me 300 push ups in 1 minute kinda trainer, this is not your guy. Rob knows...read more

 

Jay Pritzker Pavilion

Pritzker Pavilion is AWESOME. Went on a lovely evening date here last week. Sitting on the grass with a little picnic setup, listening to a concert, under...read more

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Mag Mile- Beautiful, Spacious Brownstone!
Chicago Apartment Rental Picture
  • bedrooms 2
  • community Gold Coast
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $305 - $460 /nt
 
 
 
 
 

67 reviews write a review

Luxury Resort in the Heart of Downtown Chicago
Chicago Apartment Rental Picture
  • bedrooms 2
  • community The Loop
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $399 - $439 /nt
    $9,200 - $13,170 /mth
 
 
 
 
 

61 reviews write a review

Condo close to downtown with terrace and rooftop
Chicago House Rental Picture
  • bedrooms 3
  • community East village
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $120 - $320 /nt
    $715 - $1,900 /wk
 
 
 
 
 

5 reviews write a review

B & B Boatel - Pier Gold
Chicago Houseboat Rental Picture
  • bedrooms 2
  • community Northerly Island
  • rental type Houseboat
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $500 - $600 /nt
    $1,750 /wk
    $7,000 /mth
 
 
 
 
 

5 reviews write a review

2/1 Lincoln Park Chicago - Red Line/Fullerton L 1 Blk Away
Chicago Apartment Rental Picture
  • bedrooms 2
  • community Lincoln Park
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $200 - $300 /nt
    $1,000 - $1,800 /wk
    $3,695 - $4,495 /mth
 
 
 
 
 

2 reviews write a review

Millennium Park - walk out on Michigan Ave, near public tran
Chicago Apartment Rental Picture
  • bedrooms 1
  • community Millennium Park
  • rental type Apartment
  • sleeps 3
  • baths 1
  • rates (USD) $150 - $200 /nt
    $1,000 - $1,400 /wk
    $2,800 - $3,500 /mth
 
 
 
 
 

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Loop - be close to your office, Loop, Millennium Park
Chicago Apartment Rental Picture
  • bedrooms 1
  • community The Loop
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $120 - $280 /nt
    $1,000 - $1,800 /wk
    $2,800 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

Mag Studios
Chicago Studio Rental Picture
  • bedrooms 1
  • community Edgewater Beach
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $99 - $149 /nt
    $693 - $1,043 /wk
    $2,772 - $4,172 /mth
 
 
 
 
 

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Magnolia Studios
Chicago Apartment Rental Picture
  • bedrooms 1
  • community Edgewater Beach
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $99 - $149 /nt
    $693 - $1,043 /wk
    $2,772 - $4,172 /mth
 
 
 
 
 

1 reviews write a review

Ride the Rails From West Chicago to the Windy City
Chicago Apartment Rental Picture
  • bedrooms 1
  • community West Chicago
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 8
  • baths 1
  • rates (USD) $100 - $150 /nt
    $600 - $900 /wk
    $2,000 - $3,000 /mth
 
 
 
 
 

4 reviews write a review

Penthouse with stunning views of the lake and city!
Chicago Condo Rental Picture
  • bedrooms 2
  • community Lakeshore East
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $350 - $565 /nt
 
 
 
 
 

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Beautiful 1-2 bedroom apartments, 1-2 baths, internet
Chicago Apartment Rental Picture
  • bedrooms 2
  • community Lincoln Park
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 3
  • baths 2
  • rates (USD) $1,975 - $2,800 /mth
 
 
 
 
 

3 reviews write a review

Historic Blvd 2 bdrm, 2 bath,near blue line
Chicago Apartment Rental Picture
  • bedrooms 2
  • community Logan Square
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $120 - $160 /nt
    $800 - $1,100 /wk
    $2,100 - $2,600 /mth
 
 
 
 
 

2 reviews write a review

Condo on Chicago's Gold Coast Steps from Michigan Avenue
Chicago Condo Rental Picture
  • bedrooms 2
  • community Gold Coast
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,300 - $1,700 /wk
 
 
 
 
 

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Downtown Penthouse
Chicago Apartment Rental Picture
  • bedrooms 2
  • community Magnificent Mile
  • rental type Apartment
  • sleeps 6
  • baths
  • rates (USD) $429 - $439 /nt
    $5,000 - $13,500 /mth
 
 
 
 
 

1 reviews write a review

Sleeps 1 to 4 ~ Charming&Spacious ~ Wonderful Lincoln Square ~ 4 Unit Building!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $190 - $210 /nt
 
 
 
 
 

25 reviews write a review

Large 2400 Sf Unit in Graystone - Near the Magnificent Mile - Family Friendly!
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 8
  • baths
  • rates (USD) $599 - $795 /nt
 
 
 
 
 

5 reviews write a review

Amazing Downtown Skyline Views!
Chicago Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 8
  • baths 2
  • rates (USD) $600 - $800 /nt
 
 
 
 
 

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1 BR/1 BA in Chicago Upscale Luxury Boutique Hotel--WINTER SPECIAL!!!
Chicago Hotel Rental Picture
  • bedrooms 1
  • rental type Hotel
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $200 /nt
    $1,200 /wk
    $4,400 /mth
 
 
 
 
 

13 reviews write a review

Super Week Day Value-Magnificent Mile Shopping, Rush St. Nightlife & Oak Beach !
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 22
  • baths 1
  • rates (USD) $93 - $375 /nt
    $2,775 /mth
 
 
 
 
 

13 reviews write a review

Eurasian Chic Gold Coast... Dine/Shop/Swim... Walk To Everything
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $76 - $300 /nt
    $2,275 /mth
 
 
 
 
 

16 reviews write a review

Vintage 4-br In Lincoln Square Easily Sleeps 8 - Great Introductory Rate!
Chicago Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 8
  • baths 2
  • rates (USD) $175 - $250 /nt
    $1,100 - $1,500 /wk
    $4,000 - $5,500 /mth
 
 
 
 
 

5 reviews write a review

Urban Heaven Escape! Amenities Galore! Perfect Location Email Now For Info!
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

9 reviews write a review

Amenities Galore, Amazing Views, 1350 Sq Ft of Luxury! Email Now for Info!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

17 reviews write a review

Licensed VR 1bd sleep 4 in Logan Square, Historic Apartment in Historic Neighborhood !!!
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $119 /nt
    $699 /wk
    $2,200 /mth
 
 
 
 
 

1 reviews write a review

3bds unit close to GRANT PARK
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 6
  • baths 2
  • rates (USD) $159 - $349 /nt
    $1,000 - $2,275 /wk
    $3,700 - $7,500 /mth
 
 
 
 
 

1 reviews write a review

Chicago Loop Business District. Close to Sears Tower and Public Transportation
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 3
  • baths 1
  • rates (USD) $135 - $189 /nt
    $850 - $1,200 /wk
    $3,000 - $4,200 /mth
 
 
 
 
 

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Wicker Park Russian Bathhouse 2bd LOFT
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $155 /nt
    $1,000 /wk
    $3,800 /mth
 
 
 
 
 

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Millennium Park 2bd/2ba, WALK EVERYWHERE!!!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths 2
  • rates (USD) $135 - $299 /nt
    $850 - $1,650 /wk
    $3,000 - $5,500 /mth
 
 
 
 
 

3 reviews write a review

Walk to everywhere! Millennium Park location
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $80 - $179 /nt
    $500 - $903 /wk
    $1,800 - $2,970 /mth
 
 
 
 
 

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Corporate Residences Millennium Park- Short Term or Extended S
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $225 - $299 /nt
    $1,475 - $1,600 /wk
    $5,200 - $5,500 /mth
 
 
 
 
 

6 reviews write a review

Modern Luxury In Wicker Park, 7 Day Minimum Stay
Chicago House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 5
  • rates (USD) $999 - $1,499 /nt
    $3,499 /wk
    $13,499 /mth
 
 
 
 
 

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Large 2200 SF unit in Graystone-Near The Magnificent Mile- Family Friendly!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths 2
  • rates (USD) $399 - $595 /nt
 
 
 
 
 

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Chicago Luxurious Vintage Condo on the North Shore
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 1
  • rates (USD) $199 - $269 /nt
    $1,095 - $1,545 /wk
    $2,900 - $3,600 /mth
 
 
 
 
 

25 reviews write a review

Best Choice in Chicago: Guest Favorite with Raving Reviews! Email Now for Info!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

12 reviews write a review

Magnificent Mile luxury High Rise on 28th floor with great views
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

5 reviews write a review

Great Location!! Oldtown/Lincolnpark Close to Downtown & El
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 18
  • baths 1
  • rates (USD) $250 /nt
 
 
 
 
 

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Licensed Vacation Rental,best Neighborhood Close To Wrigley, Shopping, And Dini
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $225 - $250 /nt
 
 
 
 
 

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3 Bedroom/2 Bath In Heart Of Roscoe Village
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $275 /nt
 
 
 
 
 

1 reviews write a review

Roscoe Village/Lakeview Close to Downtown Must See**
Chicago Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 10
  • baths 2
  • rates (USD) $275 /nt
 
 
 
 
 

1 reviews write a review

Lincoln Park,Depaul,Downtown-Close to El-Great Location!
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 10
  • baths 2
  • rates (USD) $375 /nt
 
 
 
 
 

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Roscoe Village Guesthouse Close to Wrigley Great Neighborhood!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 14
  • baths 2
  • rates (USD) $250 /nt
 
 
 
 
 

4 reviews write a review

Lincoln park New rehabbed and new furniture, awesome location, Depaul
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $250 /nt
 
 
 
 
 

1 reviews write a review

Roscoe Village Guesthouse Lakeview/Roscoe Village, Cubs
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $225 /nt
 
 
 
 
 

1 reviews write a review

Great Location!! Roscoe Village, Lakeview, Close to Wrigley
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $275 /nt
 
 
 
 
 

6 reviews write a review

Magnificent Mile 2 Bedroom / 2 Bathroom Suite With Great City Views
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $250 - $325 /nt
    $1,750 - $2,275 /wk
 
 
 
 
 

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24th Floor 2 bed / 2 bath with Balcony & great views in the Magnificent Mile
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

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Magnificent Mile luxury High Rise on 17th floor with Balcony
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

3 reviews write a review

New Listing! Vintage 1BR Chicago Condo w/Wifi & Private Balcony - 15 Minute Walk to Wrigley Field!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 3
  • baths 1
  • rates (USD) $130 - $150 /nt
    $775 - $900 /wk
    $3,900 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

W**O**W*2 BR/2 BA Condo in Heart of City!! Steps to Everything
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $250 /nt
 
 
 
 
 

3 reviews write a review

Beautiful New 3 Bedroom Featured On Travel Channel, Across From Wrigley Field!
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $329 - $1,029 /nt
 
 
 
 
 

25 reviews write a review

Penthouse Duplex #4 - WOW, This place is INCREDIBLE!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $550 - $855 /nt
 
 
 
 
 

30 reviews write a review

Corporate/Vacation Condominium In Popular West Loop Neighborhood, With Parking!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $226 - $270 /nt
    $1,430 - $1,680 /wk
    $3,310 /mth
 
 
 
 
 

10 reviews write a review

Ch Southport Suites - a Luxury Inn / Walk to Cubs/Wrigley Field!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 7
  • baths 1
  • rates (USD) $299 /nt
    $1,800 /wk
    $7,500 /mth
 
 
 
 
 

133 reviews write a review

Penthouse #5 - WOW, This place is FABULOUS!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $260 - $365 /nt
 
 
 
 
 

221 reviews write a review

New Listing! Unique 1BR Chicago Apartment w/Vintage Features - Walking Distance to Wrigley Field!
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $150 /nt
    $900 /wk
    $3,500 /mth
 
 
 
 
 

3 reviews write a review

Gorgeous 1 Bedroom Presidential Unit In Wyndham Chicago Grand Riverfront
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $245 - $310 /nt
 
 
 
 
 

2 reviews write a review

Large 3 bedroom in Wrigley, next to Red Line!
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 8
  • baths 1
  • rates (USD) $350 /nt
    $1,800 /wk
    $6,500 /mth
 
 
 
 
 

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$129/night in August. Downtown DISCOUNTED RATES!!!!!
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $80 - $179 /nt
    $500 - $945 /wk
    $1,800 - $3,200 /mth
 
 
 
 
 

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Wonderful Lincoln Park/DePaul Apartment In A Great Location,Only Owner Managed
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $265 - $300 /nt
    $1,844 - $2,040 /wk
    $7,700 - $7,740 /mth
 
 
 
 
 

5 reviews write a review

Fabulous Lincoln Park Apartment near DePaul Univ; Only Owner Managed
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $265 - $300 /nt
    $1,879 - $2,005 /wk
    $6,100 - $7,860 /mth
 
 
 
 
 

18 reviews write a review

3bd/2.5baX **Walk to Everything!** Breathtaking Views of the City and Lake***
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 30
  • baths
  • rates (USD)
 
 
 
 
 

1 reviews write a review

**Walk to Everything!** Stunning Views of the City and Lake!3x
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 30
  • baths
  • rates (USD) $250 - $319 /nt
 
 
 
 
 

1 reviews write a review

Luxury 2 bed/ 2 bath on 45th Floor with Balcony in Magnificent Mile
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

53 reviews write a review

Beautiful 2 Bedroom Condo In A Convenient Location On A Tree Lined Street.
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 5
  • baths 1
  • rates (USD) $115 - $160 /nt
    $850 /wk
    $3,200 /mth
 
 
 
 
 

1 reviews write a review

Charming&Spacious ~ Wonderful Lincoln Square ~ Sleeps 4 ~ in Four Unit Building!
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $175 - $195 /nt
 
 
 
 
 

12 reviews write a review

Luxury and Value Close to Everything and McCormick Place Skyline View, Hot Tub
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $170 - $225 /nt
    $1,050 - $1,375 /wk
 
 
 
 
 

32 reviews write a review

Value and Luxury. Close to City and McCormick Place. Skyline View and Hot Tub
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $160 - $225 /nt
    $1,050 - $1,375 /wk
 
 
 
 
 

75 reviews write a review

Balcony on 47th Floor - 2 bed / 2 bath with great views in Magnificent Mile
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

18 reviews write a review

Magnificent Mile with Balcony on 46th floor with great views
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

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32nd Floor with Balcony and Great Views - 2 bed / 2 bath in Magnificent Mile
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

53 reviews write a review

48th Floor 2 bed / 2 bath with Balcony & great views in the Magnificent Mile
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

55 reviews write a review

Magnificent Mile corner condo on 43rd floor with Balcony and Great Views
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

32 reviews write a review

Beautiful and Luxurious Andersonville 2 BR /2 BA
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $260 - $300 /nt
    $1,980 /wk
    $7,800 /mth
 
 
 
 
 

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Lincoln Park and Zoo Attractions Nearby
Chicago House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths 5
  • rates (USD) $750 - $825 /nt
    $5,000 - $5,750 /wk
    $17,500 - $19,750 /mth
 
 
 
 
 

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Beautiful 2 Bedroom, 2 Bath Chicago Vacation Rental Condo
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $180 - $280 /nt
    $1,340 - $1,840 /wk
    $5,400 - $7,200 /mth
 
 
 
 
 

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Last minute Sun-Thur Estate SPECIALS! Shop/Dine/Nightlife/Swim
Chicago Apartment Rental Picture
  • bedrooms 7
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 22
  • baths 5
  • rates (USD) $95 - $995 /nt
    $2,850 /mth
 
 
 
 
 

23 reviews write a review

Luxury 44th floor with Balcony-2 bed / 2 bath and great views
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $465 /nt
    $1,675 - $3,358 /wk
    $6,490 - $11,850 /mth
 
 
 
 
 

3 reviews write a review

Magnificent Northside Brownstone Home in quiet SAFE Neighborhood
Chicago House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 13
  • baths 3
  • rates (USD) $499 /nt
    $3,333 /wk
    $11,976 /mth
 
 
 
 
 

26 reviews write a review

Recently Renovated 2BR Condo in Old Town - Walk to Lake Michigan!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $400 /nt
    $2,200 /wk
    $9,429 /mth
 
 
 
 
 

4 reviews write a review

Penthouse Duplex #1 - WOW, I want to stay HERE!
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $625 - $975 /nt
 
 
 
 
 

108 reviews write a review

Penthouse Duplex #2 - WOW, This place is AMAZING!
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $625 - $975 /nt
 
 
 
 
 

45 reviews write a review

Beautiful 3 Bedroom, 1 Bathroom Chicago Vacation Rental
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 1
  • rates (USD) $175 - $210 /nt
    $1,200 /wk
    $4,200 /mth
 
 
 
 
 

2 reviews write a review

Penthouse #6 - WOW, This place is EXTRAORDINARY!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $415 - $600 /nt
 
 
 
 
 

119 reviews write a review

Luxurious 3BR with Stunning Chicago Skyline Views! Perfect Location!
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

4 reviews write a review

Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $159 - $229 /nt
 
 
 
 
 

17 reviews write a review

Wake to Sunrise Over Lake Michigan! Spacious with Stunning Views!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $225 - $240 /nt
    $1,400 /wk
 
 
 
 
 

26 reviews write a review

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft
Chicago House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 24
  • baths
  • rates (USD) $395 - $995 /nt
    $4,000 - $5,500 /wk
    $18,000 /mth
 
 
 
 
 

27 reviews write a review

Downtown Luxury Condo--October and November available!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD)
 
 
 
 
 

4 reviews write a review

Sleeps 1 to 4 ~ Spacious&Charming ~ Wonderful Lincoln Square ~ Four Unit Bldg!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $200 - $220 /nt
 
 
 
 
 

38 reviews write a review

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $195 - $250 /nt
    $950 - $1,450 /wk
    $2,450 - $4,500 /mth
 
 
 
 
 

26 reviews write a review

Penthouse Duplex #8 - WOW, This place is MAGNIFICENT!
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $625 - $975 /nt
 
 
 
 
 

3 reviews write a review

Location is Fabulous~Cozy 2bd/2BA in Brownstone on Gold Coast
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $335 - $460 /nt
 
 
 
 
 

17 reviews write a review

Penthouse Duplex #3 - WOW, This place is FANTASTIC!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $550 - $875 /nt
 
 
 
 
 

44 reviews write a review

Walk or Easy Access to Transit... 3 Bedroom...Sleeps 5
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 5
  • baths 1
  • rates (USD) $225 - $295 /nt
 
 
 
 
 

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Quick & Easy access to Brown Line 'L'...walk to lots of conveniences.
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $145 - $195 /nt
 
 
 
 
 

7 reviews write a review

Convenience Is Key... Just 2 Blocks To The Brown Line 'L'!
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $265 - $295 /nt
 
 
 
 
 

6 reviews write a review

Just 2 blocks to the Brown Line 'L' Train...
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths
  • rates (USD) $225 - $285 /nt
 
 
 
 
 

1 reviews write a review

Lovely Lincoln Square...Sleeps 4
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $165 - $185 /nt
 
 
 
 
 

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2 units 1 building// your Chicago luxury home away from home license#2314739
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • owner badgeowner badge
  • sleeps 14
  • baths 4
  • rates (USD) $195 - $995 /nt
 
 
 
 
 

5 reviews write a review

Modern 2BD 1Bth Brick-Style Ranch!
Chicago House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 10
  • baths 1
  • rates (USD) $66 - $147 /nt
 
 
 
 
 

8 reviews write a review

Downtown Chicago Luxury Home - Elegance, Comfort, Convenience
Chicago House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 11
  • baths 4
  • rates (USD) $600 - $850 /nt
    $4,900 /wk
 
 
 
 
 

15 reviews write a review

Luxurious Condo in Perfect Location ..Sleeps 8..Winter Savings
Chicago Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $225 - $300 /nt
    $1,800 /wk
    $7,500 /mth
 
 
 
 
 

16 reviews write a review

Great Location!! , Luxury, Modern- Mag Mile,Downtown, Wells
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 10
  • baths 2
  • rates (USD) $375 /nt
 
 
 
 
 

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Wrigley Retreat units 1 and 2 ... licence # 2320200
Chicago Condo Rental Picture
  • bedrooms 5
  • rental type Condo
  • sleeps 16
  • baths 2
  • rates (USD) $295 - $1,295 /nt
 
 
 
 
 

9 reviews write a review

Across From Wrigley Field, Beautiful New 1 Bedroom Featured On Travel Channel!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $199 - $579 /nt
 
 
 
 
 

30 reviews write a review

Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 9
  • baths 2
  • rates (USD) $429 - $1,270 /nt
 
 
 
 
 

27 reviews write a review

Featured On Travel Chanel With Views Of Wrigley Field, Beautiful New 4 Bedroom
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 9
  • baths 2
  • rates (USD) $429 - $1,270 /nt
 
 
 
 
 

23 reviews write a review

Stay In Luxury Overlooking The Mag Mile With Amazing Views From The 51st Floor!
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $130 - $197 /nt
    $3,900 - $5,900 /mth
 
 
 
 
 

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Penthouse Views!
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $199 /nt
    $800 - $1,200 /wk
    $3,000 /mth
 
 
 
 
 

35 reviews write a review

Penthouse #7
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $260 - $335 /nt
 
 
 
 
 

4 reviews write a review

penthouse with stunning view of Chicago
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

11 reviews write a review

Bucktown, Urban Luxury And Convenience. Easy Access To All Chicago
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 8
  • baths 2
  • rates (USD) $3,300 - $4,250 /mth
 
 
 
 
 

1 reviews write a review

Brand New Apartments in the Heart of Lincoln Park!
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths 2
  • rates (USD) $7,000 /mth
 
 
 
 
 

3 reviews write a review

Condo in Hot Bucktown / Wicker Park Neighborhood
Chicago Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $175 - $335 /nt
    $1,325 - $2,423 /wk
    $5,170 - $8,570 /mth
 
 
 
 
 

47 reviews write a review

An Architectural Icon - Award-winning, Chicago's Newest Address
Chicago Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 3
  • baths 1
  • rates (USD) $4,050 - $4,200 /mth
 
 
 
 
 

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Chicago's Lavish 1-6BR Historic Landmark. Chicago B&B License # 2288928
Chicago Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • owner badgeowner badge
  • sleeps 11
  • baths 5
  • rates (USD) $750 - $1,375 /nt
 
 
 
 
 

19 reviews write a review

2 Bed/2 Bath/ 6 Sleeps Off The Magnificent Mile
Chicago Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths 2
  • rates (USD) $500 /nt
 
 
 
 
 

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3 bedroom with new kitchen bath, pet friendly with huge yard! Walk to Wrigley!
Chicago Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 8
  • baths 1
  • rates (USD) $3,750 - $4,250 /mth
 
 
 
 
 

2 reviews write a review

4 Bedroom 3 Bath Duplex, close to Wrigley! Sleeps 8 in real beds
Chicago Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 10
  • baths 3
  • rates (USD) $8,000 /mth
 
 
 
 
 

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2000 Sq Ft Historic 2.5 Bedroom In The Heart Of Lincoln Park! Sleeps 7
Chicago House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths ½
  • rates (USD) $300 /nt
 
 
 
 
 

3 reviews write a review

The Biddle House of Old Town - Walk to Lake and Magnificent Mile!
Chicago House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $225 /nt
 
 
 
 
 

12 reviews write a review

4 Bedroom in the Heart of Lincoln Park, Clark St - Sleeps 7!
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 1
  • rates (USD) $325 /nt
 
 
 
 
 

8 reviews write a review

Lincoln Park 4 Bedroom Suite - Heart of Lincoln Park!
Chicago Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $4,980 /mth
 
 
 
 
 

10 reviews write a review

The Bucktown House - Featured on the Live Well Network!!
Chicago Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $480 /nt
 
 
 
 
 

28 reviews write a review

Beautiful River North Chicago Condo
Chicago Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 3
  • baths 1
  • rates (USD) $4,000 - $4,500 /mth
 
 
 
 
 

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Family Retreat Near McCormick Place, Parks, Museums.
Chicago House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $325 - $500 /nt
    $2,500 - $3,000 /wk
 
 
 
 
 

12 reviews write a review