Chicago 103rd Street Station vacation rentals
We found 3,363 vacation rentals — enter your dates for availability
Select the perfect private vacation rental within close proximity to Chicago 103rd Street Station (Rosemoor). Vacation homes offer the best amenities for your stay with friends, family, or just your pet, like WiFi and a washer and dryer. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Vacation rentals with weekly discounts - Chicago 103rd Street Station (Rosemoor)
Showing deals for:Nov 7 - Nov 14
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
10% off
Price is CA $450
CA $450
CA $4,498 total
CA $4,498 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $529
CA $529
CA $5,335 total
CA $5,335 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
10% off
Price is CA $758
CA $758
CA $7,468 total
CA $7,468 total
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
28% off
Price is CA $2,972
CA $2,972
CA $28,028 total
CA $28,028 total
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
10% off
Price is CA $500
CA $500
CA $4,916 total
CA $4,916 total
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, IL
10% off
Price is CA $455
CA $455
CA $4,286 total
CA $4,286 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.89.8 out of 10 rating
Exceptional
(12 reviews)
3BR Luxury Modern Apartment
Chicago, IL
10% off
Price is CA $546
CA $546
CA $5,554 total
CA $5,554 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $564
CA $564
CA $5,576 total
CA $5,576 total
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
10% off
Price is CA $572
CA $572
CA $5,785 total
CA $5,785 total
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $729
CA $729
CA $7,209 total
CA $7,209 total
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
10% off
Price is CA $439
CA $439
CA $4,344 total
CA $4,344 total
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, IL
10% off
Price is CA $543
CA $543
CA $5,461 total
CA $5,461 total
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
10% off
Price is CA $197
CA $197
CA $1,724 total
CA $1,724 total
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
19% off
Price is CA $300
CA $300
CA $3,066 total
CA $3,066 total
includes taxes & fees
Image gallery for Cheerful 4 bedroom smart home w/ indoor fireplace
8.08.0 out of 10 rating
Very good
(14 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago, IL
5% off
Price is CA $399
CA $399
CA $4,360 total
CA $4,360 total
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
10% off
Price is CA $277
CA $277
CA $2,499 total
CA $2,499 total
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
10% off
Price is CA $464
CA $464
CA $4,693 total
CA $4,693 total
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.69.6 out of 10 rating
Exceptional
(35 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
10% off
Price is CA $279
CA $279
CA $2,817 total
CA $2,817 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(19 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $777
CA $777
CA $7,225 total
CA $7,225 total
includes taxes & fees
Image gallery for NEW LUXURY PENTHOUSE CONDO
1010 out of 10 rating
Exceptional
(185 reviews)
NEW LUXURY PENTHOUSE CONDO
Chicago, IL
5% off
Price is CA $476
CA $476
CA $4,882 total
CA $4,882 total
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
10% off
Price is CA $205
CA $205
CA $2,152 total
CA $2,152 total
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
10% off
Price is CA $174
CA $174
CA $1,824 total
CA $1,824 total
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
10% off
Price is CA $433
CA $433
CA $4,288 total
CA $4,288 total
includes taxes & fees
Image gallery for Charming Miller Beach Cottage
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Charming Miller Beach Cottage
Gary, IN
10% off
Price is CA $247
CA $247
CA $2,454 total
CA $2,454 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chicago 103rd Street Station
Cheerful 4 bedroom smart home w/ indoor fireplace
Sleeps 12 · 4 bedrooms · 3+ bathrooms
8.08.0 out of 10
Very goodvery good
14 reviews(14 reviews)
Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Top rated rentals - Chicago 103rd Street Station
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)
Friend trip to Chicago
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value