Vacation rentals near Northerly Island
We found 2,928 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals near Northerly Island that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you expect for your stay, which might include a pool and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Northerly Island
Showing deals for:Nov 14 - Nov 21
Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.29.2 out of 10 rating
Wonderful
(50 reviews)
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Chicago, IL
18% off
Price is CA $249
CA $249
CA $2,567 total
CA $2,567 total
includes taxes & fees
Image gallery for Chic & Historic Apartment Steps from Mag Mile
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Chic & Historic Apartment Steps from Mag Mile
Chicago, IL
10% off
Price is CA $148
CA $148
CA $1,698 total
CA $1,698 total
includes taxes & fees
Image gallery for Downtown Charm: 2BR, Comfort, Great Amenities
1010 out of 10 rating
Exceptional
(6 reviews)
Downtown Charm: 2BR, Comfort, Great Amenities
Chicago, IL
10% off
Price is CA $442
CA $442
CA $4,498 total
CA $4,498 total
includes taxes & fees
Image gallery for Luxury SOHO Styled Two-Level Townhouse - Old Town
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury SOHO Styled Two-Level Townhouse - Old Town
Chicago, IL
10% off
Price is CA $684
CA $684
CA $6,691 total
CA $6,691 total
includes taxes & fees
Image gallery for Luxury Downtown Penthouse with Private Rooftop!
9.09.0 out of 10 rating
Wonderful
(19 reviews)
Luxury Downtown Penthouse with Private Rooftop!
Chicago, IL
5% off
Price is CA $437
CA $437
CA $4,443 total
CA $4,443 total
includes taxes & fees
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 $4,501 total
CA $4,501 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 $719
CA $719
CA $7,103 total
CA $7,103 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 $437
CA $437
CA $4,414 total
CA $4,414 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 $2,974
CA $2,974
CA $28,046 total
CA $28,046 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 $443
CA $443
CA $4,375 total
CA $4,375 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.29.2 out of 10 rating
Wonderful
(13 reviews)
3BR Luxury Modern Apartment
Chicago, IL
10% off
Price is CA $439
CA $439
CA $4,487 total
CA $4,487 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 $492
CA $492
CA $4,847 total
CA $4,847 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 $495
CA $495
CA $5,002 total
CA $5,002 total
includes taxes & fees
Image gallery for 2nd Floor Flat in River North - 2S
9.89.8 out of 10 rating
Exceptional
(21 reviews)
2nd Floor Flat in River North - 2S
Chicago, IL
5% off
Price is CA $437
CA $437
CA $4,443 total
CA $4,443 total
includes taxes & fees
Image gallery for Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
Chicago, IL
10% off
Price is CA $907
CA $907
CA $8,947 total
CA $8,947 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 $358
CA $358
CA $3,561 total
CA $3,561 total
includes taxes & fees
Image gallery for Brownstone in Gold Coast - Downtown
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Brownstone in Gold Coast - Downtown
Chicago, IL
20% off
Price is CA $124
CA $124
CA $1,443 total
CA $1,443 total
includes taxes & fees
Image gallery for Studio flat in the heart of Chicago's Gold Coast
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Studio flat in the heart of Chicago's Gold Coast
Chicago, IL
5% off
Price is CA $147
CA $147
CA $1,134 total
CA $1,134 total
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(30 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
10% off
Price is CA $402
CA $402
CA $3,699 total
CA $3,699 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 $301
CA $301
CA $3,068 total
CA $3,068 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 $4,363 total
CA $4,363 total
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, IL
8% off
Price is CA $163
CA $163
CA $1,482 total
CA $1,482 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(20 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $625
CA $625
CA $5,968 total
CA $5,968 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 $465
CA $465
CA $4,696 total
CA $4,696 total
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Northerly Island
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Find the best place to stay - Northerly Island
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
611 reviews(611 reviews)
Chic, Cozy home, by Blue Line Train Stop + Free parking
Sleeps 4 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
57 reviews(57 reviews)
Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower
Sleeps 2 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
83 reviews(83 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
874 reviews(874 reviews)
The Chicago Hotel Collection Magnificent Mile Sleek Standard Double Queen
Sleeps 4 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
Vintage Arcade Apt with Parking
Sleeps 6 · 1 bedroom · 1 bathroom
6.06.0 out of 10
2 reviews(2 reviews)
Top rated rentals - Northerly Island
Chicago vacation
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Stayed 3 nights
Quiet neighborhood.
Reggie was quick to respond to enquiries
Photos accurately represent the interior. Some nice touches with decorations.
Was nervous about parking on the street but it worked out great.
Steve P.
Stayed Aug 2024
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
186 reviews(186 reviews)
Spent 4 nights, we had everything we needed, plus nice extra touches. Location is central and close to some great neighborhoods. Jessica was very responsive and even accommodated an early check-in for a bit extra. Would definitely stay here again.
Alex P.
Stayed May 2024
Friend trip to Chicago
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
We were a group of 8 40+ yr old females. We all found the house very very clean and comfortable. We spent most of our time downtown so didn’t get a chance to explore the neighborhood too much, though we felt very safe at all times.
I would recommend this property to all.
Sarah M.
Stayed Oct 2023
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
It was a great place to stay!!
Gordon S.
Stayed Mar 2020
Great Condo, Better Service
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
This property was amazing for a college buddies reunion trip. It was spacious, exactly as advertised, and had all the amenities you can ask for. The location is great and the check-in is a breeze. The host/owner, Carole, is an absolute pro and a joy to deal with.
Would definitely stay here again.
Aaron F.
Stayed Jun 2019
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