
Chicago Jefferson Park Station vacation rentals
We found 3,815 vacation rentals — enter your dates for availability
Find the perfect vacation home within easy reach of Chicago Jefferson Park Station. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as WiFi and a hot tub. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Chicago Jefferson Park Station
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
9% off
Price is $390
$390
$2,732 for 7 nights
$2,732 for 7 nights
All fees included
Image gallery for Luxury Loft Collection 703 - Terrace - River North

1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
8% off
Price is $664
$664
$4,647 for 7 nights
$4,647 for 7 nights
All fees included
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
9% off
Price is $428
$428
$2,997 for 7 nights
$2,997 for 7 nights
All fees included
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
25% off
Price is $2,522
$2,522
$17,655 for 7 nights
$17,655 for 7 nights
All fees included
Image gallery for #1801 - Kasa Magnificent Mile Chicago

1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, IL
9% off
Price is $381
$381
$2,667 for 7 nights
$2,667 for 7 nights
All fees included
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
9% off
Price is $498
$498
$3,484 for 7 nights
$3,484 for 7 nights
All fees included
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
9% off
Price is $486
$486
$3,403 for 7 nights
$3,403 for 7 nights
All fees included
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
9% off
Price is $618
$618
$4,325 for 7 nights
$4,325 for 7 nights
All fees included
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!

1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
7% off
Price is $232
$232
$1,625 for 7 nights
$1,625 for 7 nights
All fees included
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
17% off
Price is $266
$266
$1,864 for 7 nights
$1,864 for 7 nights
All fees included
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field

9.49.4 out of 10 rating
Exceptional
(33 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is $244
$244
$1,707 for 7 nights
$1,707 for 7 nights
All fees included
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
9% off
Price is $376
$376
$2,629 for 7 nights
$2,629 for 7 nights
All fees included
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
9% off
Price is $468
$468
$3,276 for 7 nights
$3,276 for 7 nights
All fees included
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
8% off
Price is $190
$190
$1,327 for 7 nights
$1,327 for 7 nights
All fees included
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
9% off
Price is $373
$373
$2,609 for 7 nights
$2,609 for 7 nights
All fees included
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
8% off
Price is $155
$155
$1,085 for 7 nights
$1,085 for 7 nights
All fees included
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
8% off
Price is $155
$155
$1,087 for 7 nights
$1,087 for 7 nights
All fees included
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
9% off
Price is $707
$707
$4,951 for 7 nights
$4,951 for 7 nights
All fees included
Image gallery for NEW LUXURY CONDO WITH PATIO DECK

1010 out of 10 rating
Exceptional
(175 reviews)
NEW LUXURY CONDO WITH PATIO DECK
Chicago, IL
12% off
Price is $240
$240
$1,681 for 7 nights
$1,681 for 7 nights
All fees included
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.

9.89.8 out of 10 rating
Exceptional
(12 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
16% off
Price is $504
$504
$3,527 for 7 nights
$3,527 for 7 nights
All fees included
Image gallery for Cheerful 3 bedroom. Feels like home.

1010 out of 10 rating
Exceptional
(9 reviews)
Cheerful 3 bedroom. Feels like home.
Chicago, IL
16% off
Price is $210
$210
$1,471 for 7 nights
$1,471 for 7 nights
All fees included
Image gallery for ❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥

9.69.6 out of 10 rating
Exceptional
(35 reviews)
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
Chicago, IL
13% off
Price is $573
$573
$4,013 for 7 nights
$4,013 for 7 nights
All fees included
Image gallery for Cozy 4-bedroom house in adorable Evanston with WiFi, AC

9.69.6 out of 10 rating
Exceptional
(13 reviews)
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Evanston, IL
8% off
Price is $345
$345
$2,414 for 7 nights
$2,414 for 7 nights
All fees included
Image gallery for Splendid Corner 3BR in the Loop | City Views

9.49.4 out of 10 rating
Exceptional
(15 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
9% off
Price is $607
$607
$4,249 for 7 nights
$4,249 for 7 nights
All fees included
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Find the best place to stay - Chicago Jefferson Park Station
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
88 reviews(88 reviews)
Top rated rentals - Chicago Jefferson Park Station
Short trip to Chicago
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
The property was perfect for our family trip to Chicago. The house was clean, comfortable and had all of the kitchen tools we needed. We would definitely stay again on our next visit.
Aaron D.
Stayed Aug 2025
Bachelorette Haven
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Our group had a wonderful stay at the Lucky Penny. The host is so kind and professional. Her thoughtfulness extends to the perfectly appointed home and considerate details. She even has an HDMI cord available, which we used to play content from a laptop on the TV. Would highly recommend!
Angie C.
Stayed Jul 2025
Occupant
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Very clean and modern. Quite neighborhood. Great communication with manager.
Jennifer H.
Stayed Jul 2025
Fantastic
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Host was super friendly and filled us in on many things to do and places to eat! We had a great time and the property was perfect.
Shane H.
Stayed Jul 2025
Exceeded expectations
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
This was my first time using vrbo and I didn't know what to expect but I was pleasantly surprised at how amazing my host was and how this property was more amazing than the pictures. This was one of my best vacations ever.
Denise B.
Stayed Jul 2025
Love this property!
1010 out of 10
Exceptionalexceptional
125 reviews(125 reviews)
This was our second stay at this row house and we are already planning another. The house is perfect for a gathering of our adult children and grandchildren. The location is awesome - walking distance to parks, restaurants, ice cream parlor, and even the zoo. Extremely close to public transportation. House is well equipped with everything you need. Large dining table is perfect for sharing a meal and playing games!
Thomas H.
Stayed Jun 2025
Such a perfect stay
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The property was well kept, the owner was very communicative - it was the perfect place for our family to stay while in town for a wedding. I would definitely stay here again!
Sara F.
Stayed Jun 2025
Tons of Space in Chicago
1010 out of 10
Exceptionalexceptional
1 review(1 review)
What a luxury to have a full-sized house in urban Chicago! Everyone was able to have their own bedroom and bathroom and there was a full kitchen, dining, and living space so no one ever felt cramped or crowded. Plus all of the beds were queen or king sized! We also had access to a private garage behind the house, so finding parking was never an issue! The communication with the host was stellar and any question or concern was handled promptly. Two things to note: there are tenants living in the lower level of the home (using a separate entrance) and you will be able to hear them, though we never heard them during “quiet hours”. Secondly, although this house is not far from downtown Chicago, the traffic and lights will make downtown attractions typically a 30 minute drive. Just something to note, but the size and amenities more than made up for it to us! I would definitely recommend this place if you’re looking for space during your visit!
Jamie T.
Stayed Jun 2025
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- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value