Illinois Waterfront Vacation Rentals(64)
Luxury Resort in the Heart of Downtown Chicago
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$420
per night
3 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 6
May Specials! Email Now for Incredible Values!
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 2 BR,
- 2 BA,
- Sleeps 6
Michigan Ave - 3 Bedroom
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 7
$425
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 7
Beautiful River North Chicago Condo
- 1 Bedrooms,
- 1 Bathroom, Sleeps 3
$130 -
$180
per night
4 night Minimum Stay
- 1 BR,
- 1 BA,
- Sleeps 3
Lovely Streeterville Apartment
- 1 Bedrooms,
- 1 Bathroom, Sleeps 3
$140
per night
4 night Minimum Stay
- 1 BR,
- 1 BA,
- Sleeps 3
LUX 3 Bedroom on Michigan Ave
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 7
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 7
Experience the Luxury of This Beautiful Castle.
- 5 Bedrooms,
- 5 Bathrooms,
- 2 Half Baths, Sleeps 21
$850 -
$1,000
per night
2 - 3 night Minimum Stay
- 5 BR,
- 5 BA,
- 2 HF BA,
- Sleeps 21
Luxury 5br House by the Lake + Wifi + Jacuzzi! Quiet, Relaxing, Fun!
- 6 Bedrooms,
- 5 Bathrooms, Sleeps 10
$299 -
$599
per night
2 night Minimum Stay
- 6 BR,
- 5 BA,
- Sleeps 10
Penthouse with stunning views of the lake and city!
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 2 BR,
- 2 BA,
- Sleeps 6
Fantastic Downtown Chicago Condo
- 1 Bedrooms,
- 1 Bathroom, Sleeps 3
$130 -
$150
per night
4 night Minimum Stay
- 1 BR,
- 1 BA,
- Sleeps 3
Fantastic Downtown Chicago Condo
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 5
$180 -
$200
per night
4 night Minimum Stay
- 2 BR,
- 2 BA,
- Sleeps 5
Dwtn Estate... Shop/Dine/Nightlife/Swim.. Super Value!
- 2 Bedrooms, Sleeps 18
$350 -
$395
per night
3 night Minimum Stay
- 2 BR,
- Sleeps 18
Last minute Sun-Thur Estate SPECIALS! Shop/Dine/Nightlife/Swim
- 7 Bedrooms,
- 5 Bathrooms, Sleeps 22
$675 -
$995
per night
2 night Minimum Stay
- 7 BR,
- 5 BA,
- Sleeps 22
Chicago/Northside by Lake- Mini-Mansion 5 BR/4BA. Sleeps 12-14
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 14
$650 -
$700
per night
2 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 14
Fox River IL home w/ spa, home theater, hot tub & terrace
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 12
$200 -
$275
per night
2 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 12
Penthouse Views!
- 1 Bedrooms,
- 1 Bathroom, Sleeps 4
$250
per night
2 night Minimum Stay
- 1 BR,
- 1 BA,
- Sleeps 4
May Special from $135/nt -Top Location-Magnificent Mile & Navy Pier
- Studio,
- 1 Bathroom, Sleeps 4
$153 -
$158
per night
2 - 3 night Minimum Stay
- Studio,
- 1 BA,
- Sleeps 4
Beautiful home in scenic Lincoln Park for discovering Chicago
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 10
$800
per night
5 night Minimum Stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 10
Lakeshore, Millennium Park High Rise
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 2 BR,
- 2 BA,
- Sleeps 6
Your Lake Front House on Chain of Lakes Listing
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$300 -
$425
per night
2 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 10
Apple Canyon Lake Retreat - Joins us to Relax; Renew and Rejuvenate
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 7
$150 -
$375
per night
2 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 7
The Beautiful Lake of Egypt's Premier Home
- 2 Bedrooms,
- 1 Bathroom, Sleeps 6
- 2 BR,
- 1 BA,
- Sleeps 6
Tir Na Nog is a Private Country Estate - 'Ryder Cup week Available'
- 10 Bedrooms,
- 9 Half Baths, Sleeps 28
- 10 BR,
- 9 HF BA,
- Sleeps 28
41 More choices from HomeAway International Websites
Lakeside Getaway Cabin Secluded with Hot Tub, Fishing & Hiking
- 2 Bedrooms,
- 1 Bathroom, Sleeps 4
$135
per night
2 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 4
Premium Condo in Chicago's Gold Coast with Gorgeous Lake Views
- 1 Bedrooms,
- 1 Bathroom, Sleeps 4
$145 -
$395
per night
2 - 30 night Minimum Stay
- 1 BR,
- 1 BA,
- Sleeps 4
The Redbud Cottage--Beach & Quiet. Lake Sara Waterfront & Wood Fires.
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$110 -
$160
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Relaxing, lakefront retreat in beautiful Southern Illinois
- 2 Bedrooms,
- 1 Bathroom, Sleeps 5
$145
per night
2 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 5
Great Lakefront Home
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$100
per night
2 night Minimum Stay
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Carlyle Lake Lodge Sleeps 9 W/Huge Deck & (2) Boat Slips Avail
- 3 Bedrooms,
- 1 Bathroom, Sleeps 9
$175 -
$225
per night
2 night Minimum Stay
- 3 BR,
- 1 BA,
- Sleeps 9
New Beautiful Lake Front A Frame Home on Lake of Egypt
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 7
$225
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 7