Chicago Vacation Rentals in Illinois

33 properties found
Nearby rentals: Beverly Shores (37 miles), Michigan City (40 miles), New Buffalo (47 miles), Union Pier (49 miles)
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1-20 (of 33)
Chicago Illinois Vacation Rentals - Condo
Rem M.

Corporate or Vacation Rental

Chicago, Illinois

Features 2 "independent" self catering units in the same building with fully functional kitchens. Coffee, tea,...

$195 - $240 / nt

$1,350 / wk

$4,000 / mth

Condo, 3 Bedrooms, 1 Bath, Sleeps 7
Platinum
Chicago Illinois Vacation Rentals - Apartment

This is a 2 bedroom, 2 bathrooms, vintage building that has been rehabbed. This Chicago vacation rental apartment...

$120 - $180 / nt

$800 - $1,300 / wk

$2,500 - $3,000 / mth

Apartment, 2 Bedrooms, 2 Baths, Sleeps 5
Platinum
Chicago Illinois Vacation Rentals - Apartment

These Vacation Rentals are situated in the New East Side, Chicago’s newest neighborhood, a prime area of downtown...

$220 - $300 / nt

$1,400 - $2,050 / wk

$3,800 - $4,500 / mth

Apartment, 2 Bedrooms, 2 Baths, Sleeps 5
Premier+
Chicago Illinois Vacation Rentals - Apartment
Relu S.

Chicago Loop Residences

Chicago, Illinois

These Vacation Rentals are located in the Chicago LOOP, a mixed- use neighborhood west of Michigan Avenue that...

$145 - $220 / nt

$1,000 - $1,200 / wk

$2,500 - $3,000 / mth

Apartment, 1 Bedroom, 1 Bath, Sleeps 3
Premier+
Chicago Illinois Vacation Rentals - Condo

Professionally decorated, this air- conditioned, 3 bedroom condo can easily lodge up to 10 guests. All the 3...

$315 / nt

Condo, 3 Bedrooms, 2.5 Baths, Sleeps 6
Premier+
Chicago Illinois Vacation Rentals - Home

Coming to Chicago with the family and want to feel safe? Our north side / northwest side vacation rentals location...

$250 / nt

Home, 4 Bedrooms, 2 Baths, Sleeps 10
Premier+
Chicago Illinois Vacation Rentals - Apartment

Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck...

$100 - $180 / nt

$700 - $1,200 / wk

$2,500 - $3,300 / mth

Apartment, 1 Bedroom, 1 Bath, Sleeps 3
Premier+
Chicago Illinois Vacation Rentals - Condo

Professionally decorated, this air- conditioned, 3 bedroom condo can easily lodge up to 10 guests. All the 3...

$315 / nt

Condo, 3 Bedrooms, 2.5 Baths, Sleeps 10
Premier+
Chicago Illinois Vacation Rentals - Guesthouse

There are two fully furnished apartments available at the Biddle House. Each has two bedrooms, one bathroom,...

$225 / nt

$1,350 / wk

Guesthouse, 4 Bedrooms, 2 Baths, Sleeps 10
Premier+
Chicago Illinois Vacation Rentals - Apartment

The apartment is located in heart of the Chicago which are just steps to Magnificent Mile ( the Michigan Ave ),...

$935 / wk

$2,500 / mth

Apartment, Studio, 1 Bath, Sleeps 4
Plus
Lake Geneva Wisconsin Vacation Rentals - Apartment

Please note you must send an email enquiry for availability sometimes the calendar takes 24hours for up date! An...

$100 - $160 / nt

$700 - $850 / wk

$1,700 - $2,100 / mth

Apartment, 1 Bedroom, 1 Bath, Sleeps 6
Plus
Chicago Illinois Vacation Rentals - Home
Lena T.

Rent a Mansion in Chicago!

Chicago, Illinois

Rent a Mansion in Wrigleyville! Gorgeous four story home with all the elegant charm imaginable. You are guaranteed...

$750 - $1,200 / nt

$4,300 - $6,000 / wk

$13 - $18,000 / mth

Home, 5 Bedrooms, 5 Baths, Sleeps 12
Plus
Chicago Illinois Vacation Rentals - Condo
Michalina R.

Beautiful Furnished Condo

Chicago, Illinois

Corporate rental or Vacation Condo Beautiful furnished lake Michigan view, condo 1st bedroom with queen size...

$175 / nt

$3,500 / mth

Condo, 2 Bedrooms, 2 Baths, Sleeps 4
Plus
1-20 (of 33)
Annually, the Windy City attracts millions of vacationers, and according to a recent study 66% of travel planners show interest in Chicago vacation rentals. Home to illustrious Fortune 500 companies, a wealth of cultural institutions, over 500 parks, and dozens of miles of lakefront and pristine beaches, it's no surprise that this vibrant city is the third largest in the US.

The Chicago Cultural Center is not only the city’s intellectual beacon, but a thriving hub for arts as well. Its appearance is as spectacular as the treasures it houses. Finished in 1897, this striking building was intended to impress even then, and was enhanced using imported marble, mother of pearl, Favrile glass, and the finest hardwoods. All year long, the free entertainment menu features hundreds of musical performances, films, art exhibitions, and dance and theater events from regional and International artists and performers. Many Chicago vacation rentals bring you both to the center’s heart and the nearby Millennium Park.

Millennium Park continues Chicago’s top notch architectural and cultural theme in a public world-class outdoor setting on 24.5 acres of classic landscaping. Here, you can enjoy free family-friendly concerts, exhibitions, and festivals throughout the year.

Without a doubt, the Magnificent Mile is one of the premier shopping districts in the Midwest. All along Michigan Avenue to Oak Street you can shop to your heart’s content. Stores like Saks Fifth Avenue, Neiman Marcus, and Bloomingdale’s are positioned among hundreds of boutiques and specialty stores.

If you need to add Prada, Kate Spade, and other high-class designer items to your wardrobe, you will find their respective boutiques along Oak Street. In the desirable Lincoln Park neighborhood, you can stay in spacious, historic Chicago house rentals with easy access to local designer boutiques along Lincoln Avenue and Clark Street.

For Chicago vacation home rentals you’ll find pleasant coach houses near Lincoln Park, stylish suites near the lake, and lofts in the heart of downtown. Regardless of the location you won’t have to sacrifice features like gourmet kitchens, open floor plans, and hardwood floors. If you are looking for the ultimate urban vibe with spectacular views to boot, Chicago condo rentals located in modern high-rise buildings along the “Gold Coast,” just north of downtown, will deliver.

No trip to Chicago would be complete without a visit to the Lincoln Park Zoo, which is much more than just a wildlife exhibit. Here, you can also connect with nature during guided explorations among the vast gardens and discover your green thumb by consulting the horticulture experts. Or, center yourself by participating in parent and toddler yoga or adult yoga.

At the end of a pleasantly exhausting day touring this urban gem in the Midwest, kick up your feet at your metropolitan Chicago vacation rentals and relax in comfort.
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