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Luxury Vacation Rentals in Chicago


Chicago is a prime tourist destination with millions of visitors annually that come to take in the city's incredible architecture, delicious cuisine with its world-renowned deep dish pizza, and amazing city public parks such as Grant Park. Chicago is also a cultural mecca with a rich musical history with the gospel, jazz and soul music originating here. The world's largest jazz and blues festivals are held in Chicago annually. With so much to do and see, you want to be as comfortable as possible during your stay. While there are many top hotels in the city, especially if money is not an issue, there are also an increasing number of tourists who prefer to stay at the many luxury vacation rentals in Chicago.

Among the luxury vacation rentals in Chicago, you will find extravagant apartment and condos on the Magnificent Mile, but also quaint vacation house rentals in Chicago's suburbs. Choosing vacation home rentals in Chicago over hotels can be a great option for luxury travelers looking for a nice place to stay during their vacation. They can choose the property that is right for them in the city's many different neighborhoods.




Luxury Vacation Rentals in Chicago

If you're looking for a modern penthouse apartment in downtown Chicago with incredible views of Lake Michigan, there are a large number of luxury vacation rentals in Chicago's Magnificent Mile where there are many extraordinary high rise buildings. This allows you to be right in the middle of all the action and you won't have to use too much public transportation or pay for too many cabs and you can still get to many of the city's main attractions.

If you want more quaint vacation house rentals in Chicago's quieter neighborhoods such as Lakeview, Lincoln Park and Wicker Park, there are also many rentals in beautiful townhomes and brownstones that will make you feel right at home. Many of these places are close to the train or bus which makes it easy to get to downtown and all the main attractions. No matter what your preference, you are bound to find the place that is right for you.

Staying in luxury vacation rentals in Chicago instead of a hotel puts you in charge of the kind of environment you want on your trip. Perhaps you're a business traveler who wants a quiet place to work, you can pick from the many vacation house rentals in Chicago that offer a peaceful retreat where you can concentrate. Families can choose a property where both kids and adults will be the most comfortable, and have the most fun. Instead of having Chicago hotels decide what amenities they will get to enjoy, travelers can now pick the exact vacation house for rent or condo to suit their needs. Whether they need gaming consoles, cable TV, a billiards table, a Jacuzzi or hot tub, or better yet, a private pool, they can find it in one of the many vacation home rentals in Chicago.

Luxury Vacation Rentals in Chicago



Rentals also often provide fully-stocked kitchens with all the utensils, cookware and appliances you need for making a quick or elaborate meal, and get snacks on the go. If you get one of the amazing vacation house rentals in Chicago, you can also choose one with a backyard which will allow your kids to play around in, or your pets, but you can pick a place that has an outdoor grill or barbeque where you can have a relaxing meal with your family or friends on the patio or porch when you're tired of hitting the town to party and eat.

Most luxury properties with the latest amenities tend to be on the more expensive side. Properties under $200 can be found in many places around town but they tend to be studio or 1 bedroom apartments. For luxury vacation rentals that are cheaper than $100 a night, travelers can look into properties located outside of Chicago such as Lansing and Justice, Illinois.


Luxury vacation rentals in Chicago, IL

Your Home Away From Home (vacation Rental Licence 2314739)


This well kept venation rental property that sleeps 6-7 comfortably Enjoy the nice open floor plan with a nice living rooms, 2 bedrooms, 2 full bath. The condo is new hand has all upgrades and finishes of a luxury Chicago custom-built home in...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 7 Baths: 2 Half Baths: 0

Value And Luxury. Near All Attractions & Mccormick Place. Skyline View & Hot Tub


We have 2 great apartments. We have an amazing deck with an incredible skyline view of Chicago (closed in winter when there is snow and ice) and a fantastic huge hot tub. They are both great place to relax after a day of travel, sightseeing, o...


Apartment in Chicago IL
Bedrooms: 3 Sleeps: 6 Baths: 1 Half Baths: 1

Urban Luxury Home In Downtown Chicago!


Enjoy a stay at a world travelers&039; Windy City home! Modern, renovated, luxury Chicago condo is available for short or long term stays. Our ideal downtown location is just two subway stops (~10 minutes) from the loop, Michigan Ave. shopping, mus...


House in Chicago IL
Bedrooms: 3 Sleeps: 14 Baths: 3 Half Baths: 0

This Is It! Luxurious 3br W/2 Kings & Queen. Perfect Location. Book On-line Now!


If not available please check our other 3BR listing at this location VRBO #398923 and 2BR options #376149 and #408313. You just found the perfect escape...Chicago&039;s newest and most exclusive, luxurious residence will make your stay an experience ...


Apartment in Chicago IL
Bedrooms: 3 Sleeps: 6 Baths: 2 Half Baths: 0

Superb Lake And Skyline Views + Luxury Comfort At Prime Downtown Location!!


This well-appointed condo is conveniently situated in Chicago&039;s exciting South Loop. Enjoy beautiful lake and skyline views from your private balcony on the 18th Floor. Close to public transportation and many downtown attractions, including the ...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 4 Baths: 2 Half Baths: 0

Stunning Skyline Views, Amenities Galore, 1350 Sq Ft Of Luxury! Book On-line Now


If not available please check our other 2BR option at this location VRBO #653828 and 3BR options #470476 and #398923. You just found the perfect escape...Chicago&039;s newest and most exclusive, luxurious residence will make your accommodations the m...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Stunning Luxury Townhouse * Special *


Stunning brand new luxury townhouse .This sophisticated end unit, 3-story town home features exquisite mosaic, stone and marble thruout, island kitchen w/dark-stained cherry cabinets, imported granite and wallpaper , steam room and jacuzzi in hea...


Townhome in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Stay 8 At Mccormick Place!


Stay in a luxury condo literally steps from your meeting at McCormick Place! Two bedrooms, each with a queen bed, and 2 queen-sized air mattresses in the living room! Luxury finishes, private balcony! Amazing building amenities including fitness ...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 10 Baths: 2 Half Baths: 0

South Loop Luxury Sleeps 8!


Beautiful South Loop condo, short walk from Museum Campus and Michigan Avenue! Just blocks from an L hub station with easy connections to anywhere and everywhere in the city - perfect for your getaway! Right around the corner from fine shopping a...


Condo in Chicago IL
Bedrooms: 1 Sleeps: 8 Baths: 1 Half Baths: 0

Pure Chicago Luxury! 1800 Sqft 3 Bedroom / 2 Bath Near Wrigley/loyola


Live like a local in one of Chicago’s best neighborhoods at a top-rated property! Located in a family-owned boutique building in the vibrant and historic Andersonville neighborhood, our Chicago vacation property offers an affordable and comfortabl...


Condo in Chicago IL
Bedrooms: 3 Sleeps: 8 Baths: 2 Half Baths: 0

Penthouse Views!


Are you planning a trip to Chicago? You can rent furnished luxury condos, some with beautiful views of downtown Chicago and the lake. We stay in the apartments often so they are stocked with most anything you would need to cook and entertain with....


Condo in Chicago IL
Bedrooms: 1 Sleeps: 4 Baths: 1 Half Baths: 0

Modern Luxury In Wicker Park


Architecturally significant single family home in chicago&039;s best neighborhood, wicker park. This home has been featured in design magazines and is ideal for entertaining. Filled with mid-mod furnishings throughout. Forbes rated wicker park #4 in ...


House in Chicago IL
Bedrooms: 3 Sleeps: 6 Baths: 5 Half Baths: 0

Millennium Park 2bd/2ba, Walk Everywhere!!!


Posh and luxurious interiors, contemporary elegance, and a desirable location highlight , Chicago’s newest neighborhood, a prime area of downtown Chicago. Cutting edge architecture, designer shopping boutiques, world renowned restaurants, and a ni...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 4 Baths: 2 Half Baths: 0

Michigan Avenue Luxury Sleeps 10!


Stay downtown on the Magnificent Mile! Walk to the finest restaurants, shopping and attractions in River North! Brand new apartment with gorgeous city view! Great building amenities, the best neighborhood - you won&039;t want to leave. Chicago&039;s prem


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Magnificent Mile, Gold Coast Luxury Brownstone Downtown Chicago Vacation Rental


Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You&039;ve found it! Location, Location, Location! An historic 1890&039;s brownstone in the heart of the exclusive Gold Coast where Chicago&039;s elite r


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 8 Baths: 2 Half Baths: 0

Magnificent Mile Luxury High Rise On 28th Floor With Great Views


Enjoy stunning city views looking west and south. This 28th floor condo is located in the heart of the River North neighborhood in one of Chicago’s premier high rise buildings called the Grand Plaza. City of Chicago License #2179945 Encompas...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Magnificent Mile Luxury High Rise On 17th Floor With Balcony


Enjoy breathtaking city views looking west and south. This 17th floor condo is located in the heart of the River North neighborhood in one of Chicago’s premier high rise buildings called the Grand Plaza located on the corner of State Street and Gr...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxury Suite With City And Skyline Views


Brand new luxury 3 bedroom 2 bath corporate housing suite in downtown Chicago!! Picture the things you love most about the city — the pace, the style, the impression that life is happening all around you. This 3 bedroom Luxury Suite are amid th...


Condo in Chicago IL
Bedrooms: 3 Sleeps: 6 Baths: 2 Half Baths: 0

Luxury Resort In The Heart Of Downtown Chicago


Brand new luxury 2 bedroom 2 bathroom corporate housing suite in a building resort unlike anything in Chicago!! The Resort is located in Chicago&039;s high end neighborhood, Lakeshore East, where the Chicago River meets Lake Michigan. You will enjoy ...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxury Rental, Modern, A+location


Brand new 3 bedroom 2 bath fully furnished apartment in the heart of Roscoe Village. Whether you’re planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Ho...


Apartment in Chicago IL
Bedrooms: 3 Sleeps: 8 Baths: 2 Half Baths: 0

Luxury Penthouse Lincoln Park!! Close To Downtown And El


2 bedroom 2 bath fully furnished apartment in the heart of Old Town. Whether you’re planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse in Old Town a near no...


House in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxury Modern Condo, Five-star Amenties!! Hot Summer Specials!


Enjoy all the open space in this gorgeous, luxury one bedroom located at Grand Plaza in the heart of downtown Chicago. This unit is beautifully furnished with everything you will need to make you feel at home. It features wood floors, an open kitc...


Condo in Chicago IL
Bedrooms: 1 Sleeps: 5 Baths: 1 Half Baths: 0

Luxury Modern - Downtown


Near shopping in minutes. New condo building with great amenities and lux feel.


Condo in Chicago IL
Bedrooms: 3 Sleeps: 6 Baths: 2 Half Baths: 1

Luxury High Rise In The Heart Of Chicago - River And Dt Views Walk Everywhere!


UPDATE: Our sincerest apologies for delayed responses to interested guests for this property! The owner was considering an offer, as someone put one in for this condo. This VRBO is still active, but it is now a one bedroom - not the previous 2 b...


Apartment in Chicago IL
Bedrooms: 1 Sleeps: 3 Baths: 1 Half Baths: 0

Luxury Condo On 35th Floor With Balcony -2 Bed/ 2 Bath In Magnificent Mile


This 35th floor suite is located in the heart of the River North neighborhood in one of Chicago’s premier high rise buildings called the Grand Plaza located on the corner of State Street and Grand Avenue. City of Chicago License #2179945 Enc...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxury Condo - Overlooking Mag Mile, 51st Floor Amazing Views, Great Amenities!


Luxury condo in a FANTASTIC location! Perfect for vacation, short-term or corporate rental. High-rise condominium situated in Chicago&039;s premium Gold Coast/River North neighborhood. Infused with many amenities and outstanding views of the City a...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 4 Baths: 2 Half Baths: 0

Luxury And Value.near All Attractions & Mccormick Place. Skyline View & Hot Tub


We have 2 great apartments. We have an amazing deck with an incredible skyline view of Chicago (closed in winter when there is snow and ice) and a fantastic huge hot tub. They are both great place to relax after a day of travel, sightseeing, o...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 1 Half Baths: 1

Luxury 44th Floor With Balcony-2 Bed / 2 Bath And Great Views


Stay in this 44th floor brand new luxury high rise building completed in 2013. Experience breathtaking city views in this Amli River North building located on the corner of Clark and Hubbard Street. City of Chicago License #2288913 This buil...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxury 2 Bed/ 2 Bath On 45th Floor With Balcony In Magnificent Mile


Enjoy stunning panoramic city views looking northeast to southwest. This 45th floor unit is located in the heart of the River North neighborhood in one of Chicago’s premier high rise buildings on the corner of State Street and Grand Avenue. Cit...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxurious Penthouse At Parc Huron! Walk Everywhere! Reserve On-line Now!


If not available please check our other 2BR options at this location VRBO #408313 and #653828. Also 3BR options #470476 and #398923. You just found the perfect escape...Chicago&039;s newest and most exclusive, luxurious residence will help make you...


Condo in Chicago IL
Bedrooms: 2 Sleeps: 6 Baths: 2 Half Baths: 0

Luxurious North Shore Chicago Condo


The Sky View Condo at Residence on the Avenue is Spacious 1800 sq.ft. home in a stunning blonde brick/limestone 1928 building on a tree lined avenue. A very quiet and secure 4 unit building with front lobby entrance.The entrance boxwood garden wh...


Condo in Chicago IL
Bedrooms: 3 Sleeps: 8 Baths: 2 Half Baths: 0

Luxurious Downtown 2br Apt By Chicago River


This beautiful building is perfectly located in Downtown Chicago alongside the Chicago River. Guests will have free access to the building&039;s finest amenities. Enjoy the spectacular views of Downtown Chicago on our two level, outdoor sundeck compl...


Apartment in Chicago IL
Bedrooms: 2 Sleeps: 5 Baths: 2 Half Baths: 0

Luxurious Condo In Perfect Location ..sleeps 8.


Enjoy your Chicago visit from one of the best locations in the city. Nearby are great restaurants and bars, shopping, a fabulous park, and a famous award winning bakery. Get out and enjoy the city or relax in our luxurious accommodations. Spaci...


Condo in Chicago IL
Bedrooms: 3 Sleeps: 8 Baths: 2 Half Baths: 0




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