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Vacation Rentals
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Illinois
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Chicago
2
BR /
2
BA /
Sleeps
6
From $225/nt
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2
BR /
2
BA /
Sleeps
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From $225/nt
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BA /
Sleeps
3
Featured
Chicago Lake Vacation Rentals
(81)
sort by
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Availability Last Updated
Accepts Online Payments
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Bedrooms: Most to Least
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Price: Low to High
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Special Offers First
Magnificent Mile, Gold Coast Luxury Brownstone Downtown Chicago Vacation Rental
2 Bedrooms,
2
Bathrooms
, Sleeps 8
$305 - $460
per night
Magnificent Mile, Gold Coast Luxury Brownstone Downtown Chicago Vacation Rental
Book it Now!
2 night minimum stay
2
BR,
2
BA,
Sleeps
8
Illinois
>
Chicago Apartment
#188897
(54)
Compare
Penthouse #5
1 Bedrooms,
1
Bathroom
, Sleeps 4
$250 - $300
per night
Penthouse #5
Book it Now!
3 night minimum stay
1
BR,
1
BA,
Sleeps
4
Illinois
>
Chicago Condo
#65673vb
(197)
Compare
Grand Plaza Penthouse #6
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$400 - $500
per night
Grand Plaza Penthouse #6
Book it Now!
3 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#72685vb
(103)
Compare
Luxury 2 bedroom on 47th Floor with great views in Magnificent Mile
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$225 - $464
per night
Luxury 2 bedroom on 47th Floor with great views in Magnificent Mile
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#379083
(12)
Compare
Magnificent Mile Luxury Corner Unit on 45th Floor with great views
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$225 - $464
per night
Magnificent Mile Luxury Corner Unit on 45th Floor with great views
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#358005
(34)
Compare
Luxury Resort in the Heart of Downtown Chicago
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$429
per night
Luxury Resort in the Heart of Downtown Chicago
3 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#242128
(47)
Compare
Downtown Chicago Luxury Home - Elegance, Comfort, Convenience
4 Bedrooms,
4
Bathrooms
, Sleeps 11
$600 - $850
per night
Downtown Chicago Luxury Home - Elegance, Comfort, Convenience
3 - 5 night minimum stay
4
BR,
4
BA,
Sleeps
11
Illinois
>
Chicago House
#154813
(15)
Compare
Chicago Luxurious Vintage Condo on the North Shore
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Chicago Luxurious Vintage Condo on the North Shore
3
BR,
2
BA,
Sleeps
8
Illinois
>
Chicago Condo
#282600
(18)
Compare
Chicago Luxurious Vintage Vacation Condo
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Chicago Luxurious Vintage Vacation Condo
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#285318
(17)
Compare
Magnificent Mile luxury High Rise on 28th floor with great views
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$225 - $464
per night
Magnificent Mile luxury High Rise on 28th floor with great views
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#908613
(5)
Compare
Luxurious Condo in Perfect Location ..Sleeps 8..Winter Savings
3 Bedrooms, Sleeps 8
$225 - $300
per night
Luxurious Condo in Perfect Location ..Sleeps 8..Winter Savings
2 - 3 night minimum stay
3
BR,
Sleeps
8
Illinois
>
Chicago Condo
#277850
(13)
Compare
Michigan Ave - 3 Bedroom
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 7
$425
per night
Michigan Ave - 3 Bedroom
3 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
7
Illinois
>
Chicago Condo
#3013292
Compare
Beautiful River North Chicago Condo
1 Bedrooms,
1
Bathroom
, Sleeps 3
$130 - $180
per night
Beautiful River North Chicago Condo
4 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Condo
#3485336
Compare
Penthouse on Michigan Ave | Skyline and Lake Views | Downtown Loop
3 Bedrooms,
2
Bathrooms
, Sleeps 7
Penthouse on Michigan Ave | Skyline and Lake Views | Downtown Loop
3
BR,
2
BA,
Sleeps
7
Illinois
>
Chicago Condo
#3025053
(5)
Compare
Lovely Streeterville Apartment
1 Bedrooms,
1
Bathroom
, Sleeps 3
$140
per night
Lovely Streeterville Apartment
4 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Apartment
#3500726
Compare
**Walk to Everything!** Stunning Views of the City and Lake!3x
3 Bedrooms, Sleeps 30
**Walk to Everything!** Stunning Views of the City and Lake!3x
3
BR,
Sleeps
30
Illinois
>
Chicago Condo
#282940vb
Compare
LUX 3 Bedroom on Michigan Ave
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 7
LUX 3 Bedroom on Michigan Ave
3
BR,
2
BA,
1
HF BA,
Sleeps
7
Illinois
>
Chicago Condo
#3010289
(5)
Compare
3bd/2.5baX ** Walk to Everything! *** Stunning Views of the Lake and City
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
3bd/2.5baX ** Walk to Everything! *** Stunning Views of the Lake and City
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Illinois
>
Chicago Condo
#267015
1 Review
Compare
$129/night after Oct 15th !!! Close to Lincoln Prk. Free St Parking!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$129/night after Oct 15th !!! Close to Lincoln Prk. Free St Parking!
2
BR,
2
BA,
Sleeps
4
Illinois
>
Chicago Apartment
#391032
1 Review
Compare
Luxury 2 bedroom on 48th Floor with great views in Magnificent Mile
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$225 - $464
per night
Luxury 2 bedroom on 48th Floor with great views in Magnificent Mile
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#358020
(34)
Compare
Great views-Luxury 2 bedroom on 32nd Floor Magnificent Mile
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$225 - $464
per night
Great views-Luxury 2 bedroom on 32nd Floor Magnificent Mile
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#358006
(29)
Compare
Magnificent Mile luxury High Rise on 43rd floor with great views
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$225 - $464
per night
Magnificent Mile luxury High Rise on 43rd floor with great views
3 - 7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#358013
(26)
Compare
Beautiful and Luxurious 3 Bedroom / 2 Bathroom Condo
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$250 - $360
per night
Beautiful and Luxurious 3 Bedroom / 2 Bathroom Condo
3 - 4 night minimum stay
3
BR,
2
BA,
Sleeps
8
Illinois
>
Chicago Condo
#247326
(42)
Compare
Spacious 2 bed, 2 bath luxury apartment close to Mag Mile.
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$1,400
per week
Spacious 2 bed, 2 bath luxury apartment close to Mag Mile.
7 night minimum stay
2
BR,
2
BA,
Sleeps
4
Illinois
>
Chicago Condo
#950736
1 Review
Compare
The North Side Suites - 4 Bedroom - blocks from Magnificent Mile,
4 Bedrooms,
2
Bathrooms
, Sleeps 10
$375
per night
The North Side Suites - 4 Bedroom - blocks from Magnificent Mile,
3 night minimum stay
4
BR,
2
BA,
Sleeps
10
Illinois
>
Chicago Apartment
#235477
1 Review
Compare
Magnificent Mile Studio, Steps From Michigan Ave
Studio,
1
Bathroom
, Sleeps 2
$155 - $165
per night
Magnificent Mile Studio, Steps From Michigan Ave
3 night minimum stay
Studio,
1
BA,
Sleeps
2
Illinois
>
Chicago Apartment
#237119
Compare
Lincoln Park Suite - 4 Bed, 2 Bath - Sleeps 8
4 Bedrooms,
2
Bathrooms
, Sleeps 10
$4,980
per month
Lincoln Park Suite - 4 Bed, 2 Bath - Sleeps 8
30 night minimum stay
4
BR,
2
BA,
Sleeps
10
Illinois
>
Chicago Apartment
#236651
Compare
Penthouse with stunning views of the lake and city!
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Penthouse with stunning views of the lake and city!
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#3465475
(8)
Compare
Fantastic Downtown Chicago Condo
1 Bedrooms,
1
Bathroom
, Sleeps 3
$130 - $150
per night
Fantastic Downtown Chicago Condo
4 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Condo
#3472100
Compare
Fantastic Downtown Chicago Condo
2 Bedrooms,
2
Bathrooms
, Sleeps 5
$180 - $200
per night
Fantastic Downtown Chicago Condo
4 night minimum stay
2
BR,
2
BA,
Sleeps
5
Illinois
>
Chicago Condo
#3486085
Compare
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