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Far North Side Holiday Rentals

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Our top choices for Far North Side holiday rentals

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (82 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is NZ$363
includes taxes & fees
5 July - 6 July
Cozy studio in Andersonville Chicago

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (55 reviews)
"So hospitable "
United States
Adrian
The price is NZ$1,124
includes taxes & fees
2 July - 3 July
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
7.8 out of 10, Good, (9 reviews)
"Everything was great- great location, very clean and cute, and the hosts were communicative and attentive. "
United States
Elizabeth A.
The price is NZ$388
includes taxes & fees
24 June - 25 June
1BR/1BA City Comfort

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (1 review)
The price is NZ$766
includes taxes & fees
23 June - 24 June
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

1BR Near O'Hare • Balcony • Workspace

1BR Near O'Hare • Balcony • Workspace
O'Hare
The price is NZ$519
includes taxes & fees
22 June - 23 June
1BR Near O'Hare • Balcony • Workspace

Modern 1BR w/ Workspace near O'Hare

Modern 1BR w/ Workspace near O'Hare
O'Hare
The price is NZ$559
includes taxes & fees
15 July - 16 July
Modern 1BR w/ Workspace near O'Hare

Mins from O'Hare • Safe Location • Private Parking

Mins from O'Hare • Safe Location • Private Parking
O'Hare
The price is NZ$451
includes taxes & fees
22 June - 23 June
Mins from O'Hare • Safe Location • Private Parking

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
8.0 out of 10, Very good, (11 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
The price is NZ$500
includes taxes & fees
18 June - 19 June
Cozy apartment with AC and WiFi in awesome Chicago

Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.4 out of 10, Very good, (10 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is NZ$847
includes taxes & fees
30 June - 1 July
Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is NZ$511
includes taxes & fees
25 June - 26 June
Comfortable 2BR Chicago Apt

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.4 out of 10, Very good, (14 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
The price is NZ$355
includes taxes & fees
24 June - 25 June
Sunlit Studio with City Charm

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
The price is NZ$695
includes taxes & fees
7 July - 8 July
2BR • Newly Furnished Modern Apt • Near O'Hare

Ideal 2BR Getaway Close to Attractions

Ideal 2BR Getaway Close to Attractions
Rogers Park
8.0 out of 10, Very good, (8 reviews)
"Host was fantastic and property excellent!"
United States
David R.
The price is NZ$518
includes taxes & fees
22 June - 23 June
Ideal 2BR Getaway Close to Attractions

Delightful 1BR Apt in Ravenswood

Delightful 1BR Apt in Ravenswood
Uptown
8.4 out of 10, Very good, (6 reviews)
"Clean, accurate to picture, excellent location, easy communication with hosts. Definite street noise (and we were there during road construction, so it was a lot), but I expect normal for the location."
United States
Tasleem
The price is NZ$382
includes taxes & fees
22 June - 23 June
Delightful 1BR Apt in Ravenswood

Modern Condo • Safe Chicago Stay Near O’Hare

Modern Condo • Safe Chicago Stay Near O’Hare
O'Hare
10.0 out of 10, Exceptional, (1 review)
"The overall experience was fantastic. The unit was clean and well stocked to meet all my needs for the stay. Staff were very responsive and helpful with all inquires"
United States
Jatin P.
The price is NZ$616
includes taxes & fees
9 July - 10 July
Modern Condo • Safe Chicago Stay Near O’Hare

Cozy 1BR Apartment in Rogers Park

Cozy 1BR Apartment in Rogers Park
Rogers Park
7.6 out of 10, Good, (4 reviews)
"Very clean, excellent communication with the host and location was perfect."
United States
JoEllen K.
The price is NZ$396
includes taxes & fees
22 June - 23 June
Cozy 1BR Apartment in Rogers Park

Bright & Cozy Chicago 1BR | Near Dining & Transit

Bright & Cozy Chicago 1BR | Near Dining & Transit
West Ridge
7.6 out of 10, Good, (5 reviews)
"The place was bery nice and we enjoyed our stay."
United States
Peter T.
The price is NZ$360
includes taxes & fees
22 June - 23 June
Bright & Cozy Chicago 1BR | Near Dining & Transit

Elegant 2BR Apartment w/ In-Unit Laundry

Elegant 2BR Apartment w/ In-Unit Laundry
Uptown
9.0 out of 10, Wonderful, (19 reviews)
"Very nice apartment. Looks just like the pictures. Host had great communication. Definitely would stay here again. "
United States
Timothy S.
The price is NZ$545
includes taxes & fees
22 June - 23 June
Elegant 2BR Apartment w/ In-Unit Laundry

Cozy & Inviting 2BR Apartment

Cozy & Inviting 2BR Apartment
Albany Park
7.0 out of 10, Good, (2 reviews)
"Pictures DID NOT represent a clear depiction of what we were getting. After looking deeper and zooming in on the pictures, it was clear that they had been edited. Not clean, toothpaste on the bathroom vanity. No toilet paper, paper towels, or garbage bags upon arrival. Rugs were stained and filthy. Second bedroom was at least 15 degrees colder than the main bedroom and rest of the apartment. Communication was somewhat odd, I felt like we were being watched or something. Also was told that my...
United States
Samantha N.
The price is NZ$386
includes taxes & fees
22 June - 23 June
Cozy & Inviting 2BR Apartment

Warm & Stylish 2BR Apt

Warm & Stylish 2BR Apt
Albany Park
10.0 out of 10, Exceptional, (3 reviews)
"Clean and warm (on a bitter winter’s night)"
United States
Thomas V.
The price is NZ$519
includes taxes & fees
1 July - 2 July
Warm & Stylish 2BR Apt
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Far North Side Hotel Reviews

Find out more about Far North Side

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Far North Side holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Far North Side. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Far North Side. Seeing all the best attractions is bound to make you fall in love with Far North Side. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Far North Side short-term rentals, that won’t be hard to do.

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