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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (102 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
$113 nightly
The price is $139
Nov 2 - Nov 3
Total with taxes and fees
Cozy studio in Andersonville Chicago
A hotel room with a bed, a view of a cityscape, and a window with curtains.

2. 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.
$263 nightly
The price is $270
Oct 12 - Oct 13
Total with taxes and fees
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
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, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
$287 nightly
The price is $346
Oct 12 - Oct 13
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A hotel room with a bed, a desk, a chair, a radiator, a ceiling fan, and a window with curtains.

4. Sunny Studio in Heart of Ravenswood

Sunny Studio in Heart of Ravenswood
Uptown
$204 nightly
The price is $222
Oct 26 - Oct 27
Total with taxes and fees
Sunny Studio in Heart of Ravenswood
Living area

5. Deluxe 1BR Near Shops & Cafés

Deluxe 1BR Near Shops & Cafés
Edgewater
$253 nightly
The price is $278
Oct 26 - Oct 27
Total with taxes and fees
Deluxe 1BR Near Shops & Cafés
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.

6. Delightful 1BR Apt in Ravenswood

Delightful 1BR Apt in Ravenswood
Uptown
$257 nightly
The price is $282
Nov 2 - Nov 3
Total with taxes and fees
Delightful 1BR Apt in Ravenswood
A compact kitchen with a gas stove, microwave, and a coffee maker on a small table.

7. Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
$201 nightly
The price is $218
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.

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

Chill & Cozy 2BR Apt | Walk to Parks, Food & More!
North Park
$238 nightly
The price is $266
Nov 2 - Nov 3
Total with taxes and fees
Chill & Cozy 2BR Apt | Walk to Parks, Food & More!
A hotel room with a large bed, two bedside tables with lamps, a painting on the wall, and a textured blanket.

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

Bright & Cozy Chicago 1BR | Near Dining & Transit
West Ridge
$253 nightly
The price is $278
Oct 19 - Oct 20
Total with taxes and fees
Bright & Cozy Chicago 1BR | Near Dining & Transit
A compact kitchen with wooden cabinets, a stainless steel refrigerator, a wooden dining table with a black chair, and a wall-mounted round mirror.

10. 1BR Pad with Homey Feel

1BR Pad with Homey Feel
Lincoln Square
$244 nightly
The price is $267
Oct 26 - Oct 27
Total with taxes and fees
1BR Pad with Homey Feel
A round white table with two brown leather chairs, a glass vase with a plant, and a piece of abstract art on the wall.

11. Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
$223 nightly
The price is $242
Nov 3 - Nov 4
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
A modern living room with a flat-screen TV, two sofas, a coffee table, and a potted plant.

12. Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
$249 nightly
The price is $279
Nov 2 - Nov 3
Total with taxes and fees
Great Layout – Spacious 2BR Apt
A bedroom with a bed, a radiator, a window with curtains, a ceiling fan, and a wall-mounted artwork.

13. Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
$233 nightly
The price is $254
Oct 18 - Oct 19
Total with taxes and fees
Homey 1BR Space Apartment
Room

14. Modern City Vibes | 1BR Stay

Modern City Vibes | 1BR Stay
Rogers Park
$253 nightly
The price is $278
Oct 28 - Oct 29
Total with taxes and fees
Modern City Vibes | 1BR Stay
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.

15. Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
$217 nightly
The price is $241
Oct 26 - Oct 27
Total with taxes and fees
Comfortable 2BR Chicago Apt
Private kitchen

16. 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.
$174 nightly
The price is $193
Oct 19 - Oct 20
Total with taxes and fees
1BR Serene and Cozy Chicago 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
$217 nightly
The price is $241
Oct 26 - Oct 27
Total with taxes and fees
Cozy & Inviting 2BR Apartment
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

18. Chic apartment with fitness room and AC in beautiful Chicago

Chic apartment with fitness room and AC in beautiful Chicago
Rogers Park
6.4 out of 10, (7 reviews)
"Everything was smooth and efficient "
United States
Brande M.
$299 nightly
The price is $369
Oct 15 - Oct 16
Total with taxes and fees
Chic apartment with fitness room and AC in beautiful Chicago
A modern living room with a sectional sofa, a round coffee table, and a floor lamp.

19. 2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
$306 nightly
The price is $362
Oct 14 - Oct 15
Total with taxes and fees
2BR • Newly Furnished Modern Apt • Near O'Hare
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Well appointed rooms, kind staff, and very responsive"
Whitney 3-night trip
Posted less than an hour ago
Fairmont Chicago at Millennium Park

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.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Far North Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

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

Whenever you want to travel, a warm welcome awaits you in Far North Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Far North Side in high season.

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 $82 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

At Expedia, we put the best Far North Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

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.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Far North Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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