A busy indoor space with a high, curved ceiling and a large circular light fixture.

Far North Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Far North Side vacation rentals

A modern bedroom with a bed, a sofa, and a hanging plant.

1. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (104 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
$113 nightly
The price is $139
Nov 2 - Nov 3
Total with taxes and fees
Cozy studio in Andersonville Chicago
A kitchen with a white refrigerator, a stove, a sink, wooden cabinets, and a window with blinds.

2. Cozy 1BR in Walkable Area

Cozy 1BR in Walkable Area
Lincoln Square
10.0 out of 10, Exceptional, (1 review)
"Exactly as described. Classic Chicago walkup in a quiet building and neighborhood!"
United States
Craig R.
$173 nightly
The price is $192
Oct 19 - Oct 20
Total with taxes and fees
Cozy 1BR in Walkable Area
A rooftop terrace with a brick wall, large windows, and a metal railing.

3. 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, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
$296 nightly
The price is $356
Oct 21 - Oct 22
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Living area

4. Deluxe 1BR Near Shops & Cafés

Deluxe 1BR Near Shops & Cafés
Edgewater
$216 nightly
The price is $234
Nov 16 - Nov 17
Total with taxes and fees
Deluxe 1BR Near Shops & Cafés
A hotel room with a large bed, two bedside tables with lamps, a painting on the wall, and a textured blanket.

5. Bright & Cozy Chicago 1BR | Near Dining & Transit

Bright & Cozy Chicago 1BR | Near Dining & Transit
West Ridge
$230 nightly
The price is $251
Oct 27 - Oct 28
Total with taxes and fees
Bright & Cozy Chicago 1BR | Near Dining & Transit
A hotel room with a bed, a desk, a chair, a radiator, a ceiling fan, and a window with curtains.

6. Sunny Studio in Heart of Ravenswood

Sunny Studio in Heart of Ravenswood
Uptown
10.0 out of 10, Exceptional, (1 review)
"."
United States
Patrick V.
$200 nightly
The price is $217
Nov 9 - Nov 10
Total with taxes and fees
Sunny Studio in Heart of Ravenswood
Living area

7. 1BR Serene and Cozy Chicago Apt!

1BR Serene and Cozy Chicago Apt!
Albany Park
8.0 out of 10, Very good, (1 review)
"The room and apartment were clean"
United States
Maximilian W.
$186 nightly
The price is $207
Nov 16 - Nov 17
Total with taxes and fees
1BR Serene and Cozy Chicago Apt!
A modern living room with a dark grey sofa, a white coffee table, and a floor lamp. A kitchen with dark wooden cabinets, stainless steel appliances, and a white countertop is visible in the background.

8. Delightful 1BR Apt in Ravenswood

Delightful 1BR Apt in Ravenswood
Uptown
$240 nightly
The price is $262
Oct 26 - Oct 27
Total with taxes and fees
Delightful 1BR Apt in Ravenswood
A modern bedroom with a bed, a window, and a view of an outdoor area.

9. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (27 reviews)
"Great place! Highly recommended."
United States
Ian
$377 nightly
The price is $464
Oct 19 - Oct 20
Total with taxes and fees
The Lincoln Square Hideaway
A bedroom with a bed, a radiator, a window with curtains, a ceiling fan, and a wall-mounted artwork.

10. Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
$235 nightly
The price is $257
Oct 18 - Oct 19
Total with taxes and fees
Homey 1BR Space Apartment
A compact kitchen with a gas stove, microwave, and a coffee maker on a small table.

11. Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
$206 nightly
The price is $224
Oct 27 - Oct 28
Total with taxes and fees
Sunlit Studio with City Charm
A living room with a sofa, two armchairs, a coffee table, a lamp, and a view of a building outside.

12. Chill & Cozy 2BR Apt | Walk to Parks, Food & More!

Chill & Cozy 2BR Apt | Walk to Parks, Food & More!
North Park
$206 nightly
The price is $228
Oct 26 - Oct 27
Total with taxes and fees
Chill & Cozy 2BR Apt | Walk to Parks, Food & More!
A round white table with two brown leather chairs, a glass vase with a plant, and a piece of abstract art on the wall.

13. Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
$228 nightly
The price is $248
Nov 4 - Nov 5
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
Living area

14. Modern City Vibes | 1BR Stay

Modern City Vibes | 1BR Stay
Rogers Park
$245 nightly
The price is $268
Oct 27 - Oct 28
Total with taxes and fees
Modern City Vibes | 1BR Stay
A compact kitchen with wooden cabinets, a stainless steel refrigerator, a wooden dining table with a black chair, and a wall-mounted round mirror.

15. 1BR Pad with Homey Feel

1BR Pad with Homey Feel
Lincoln Square
$226 nightly
The price is $246
Nov 4 - Nov 5
Total with taxes and fees
1BR Pad with Homey Feel
A modern living room with a flat-screen TV, two sofas, a coffee table, and a potted plant.

16. Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
$217 nightly
The price is $241
Oct 26 - Oct 27
Total with taxes and fees
Great Layout – Spacious 2BR Apt
A living room with a sofa, a coffee table, a chair, a ceiling fan, and a door leading to an outdoor area.

17. Cozy & Inviting 2BR Apartment

Cozy & Inviting 2BR Apartment
Albany Park
$206 nightly
The price is $228
Oct 26 - Oct 27
Total with taxes and fees
Cozy & Inviting 2BR Apartment
A hotel room with a bed, a view of a cityscape, and a window with curtains.

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

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
$334 nightly
The price is $344
Oct 20 - Oct 21
Total with taxes and fees
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A dining area with a table set for four, a sofa, a television, and a plant.

19. 3BR Rogers Park Apt Near Loyola & Lake Michigan

3BR Rogers Park Apt Near Loyola & Lake Michigan
Rogers Park
$252 nightly
The price is $280
Oct 27 - Oct 28
Total with taxes and fees
3BR Rogers Park Apt Near Loyola & Lake Michigan
A living room with a flat-screen TV mounted on the wall, a wooden cabinet below, a black mat on the floor, a coffee table with a tissue box, and a potted plant.

20. Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
$221 nightly
The price is $246
Oct 21 - Oct 22
Total with taxes and fees
Comfortable 2BR Chicago 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

The Wade

The Wade

10/10 Excellent
"Loved this trendy hotel. Great location, amenities, and service."
Sheilaann 3-night trip
Posted 1 hour ago
The Wade

Find out more about Far North Side

Everything you need to know about Far North Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Far North Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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Far North Side vacation rentals: An excellent choice for every season

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Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $81 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Far North Side rentals

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To find some top Far North Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Far North Side vacation.

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