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 rooftop terrace with a brick wall, large windows, and a metal railing.

1. 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
A modern bedroom with a bed, a sofa, and a hanging plant.

2. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 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 hotel room with a bed, a view of a cityscape, and a window with curtains.

3. 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 modern bedroom with a bed, a window, and a view of an outdoor area.

4. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (26 reviews)
"We had a great time it was an awesome place and we would definitely stay there again! The host was great the place was well equipped and in a great location for us!!"
United States
Wendy T.
$377 nightly
The price is $464
Oct 19 - Oct 20
Total with taxes and fees
The Lincoln Square Hideaway
A kitchen with a white refrigerator, a stove, a sink, wooden cabinets, and a window with blinds.

5. 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.
$174 nightly
The price is $193
Oct 19 - Oct 20
Total with taxes and fees
Cozy 1BR in Walkable Area
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.
$204 nightly
The price is $222
Nov 9 - Nov 10
Total with taxes and fees
Sunny Studio in Heart of Ravenswood
A living room with a white sofa, a decorative vase with a plant, a small wooden figurine, and a gold decorative piece on a white coffee table.

7. 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, (6 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
$395 nightly
The price is $466
Oct 18 - Oct 19
Total with taxes and fees
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

8. Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.4 out of 10, Good, (16 reviews)
"Great location and clean room! Host was very responsive and helpful!"
United States
Andrew O.
$341 nightly
The price is $421
Oct 20 - Oct 21
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
Private kitchen

9. 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 29 - Oct 30
Total with taxes and fees
1BR Serene and Cozy Chicago Apt!
A modern bedroom with a large bed, two bedside tables, and a window with blinds.

10. Elegant 2BR Apartment w/ In-Unit Laundry

Elegant 2BR Apartment w/ In-Unit Laundry
Uptown
$246 nightly
The price is $276
Oct 26 - Oct 27
Total with taxes and fees
Elegant 2BR Apartment w/ In-Unit Laundry
A dining table with a vase of white flowers, a bottle of wine, glasses, and a wooden board with strawberries and cheese.

11. Walk to the Beach • Private Office • 5BR

Walk to the Beach • Private Office • 5BR
Rogers Park
8.0 out of 10, Very good, (13 reviews)
"We had a great stay and plenty of room for our group of 8 - our host was very communicative and responsive - would stay here again"
United States
Jay B.
$573 nightly
The price is $672
Oct 22 - Oct 23
Total with taxes and fees
Walk to the Beach • Private Office • 5BR
A modern living room with a green sectional sofa, a patterned rug, and artwork on the walls.

12. The Velvet Manor | 2BR Boutique Stay

The Velvet Manor | 2BR Boutique Stay
Uptown
10.0 out of 10, Exceptional, (2 reviews)
"This is a very nice property and an excellent location in Andersonville - just a few short steps to Clark Street. We hope to join you again someday soon - thank you!"
United States
Michael K.
$437 nightly
The price is $525
Nov 2 - Nov 3
Total with taxes and fees
The Velvet Manor | 2BR Boutique Stay
A modern kitchen with white cabinetry, stainless steel appliances, and a marble backsplash.

13. Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.

Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.
Uptown
10.0 out of 10, Exceptional, (1 review)
"First, the place is beautiful. The location is pretty perfect too. I'm a big fan of dining out and there were some fantastic spots walkable, so that was a big plus. The host was communicative and friendly. The little welcome gifts were a nice perk too. Will definitely be back next time I'm in town."
United States
Collin M.
$593 nightly
The price is $701
Nov 3 - Nov 4
Total with taxes and fees
Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.
A living room with a sofa, two armchairs, a coffee table, a lamp, and a view of a building outside.

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

Chill & Cozy 2BR Apt | Walk to Parks, Food & More!
North Park
$223 nightly
The price is $248
Nov 9 - Nov 10
Total with taxes and fees
Chill & Cozy 2BR Apt | Walk to Parks, Food & More!
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.

15. Delightful 1BR Apt in Ravenswood

Delightful 1BR Apt in Ravenswood
Uptown
$241 nightly
The price is $264
Oct 26 - Oct 27
Total with taxes and fees
Delightful 1BR Apt in Ravenswood
Living area

16. Deluxe 1BR Near Shops & Cafés

Deluxe 1BR Near Shops & Cafés
Edgewater
$225 nightly
The price is $245
Nov 1 - Nov 2
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.

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

Bright & Cozy Chicago 1BR | Near Dining & Transit
West Ridge
$230 nightly
The price is $251
Oct 26 - Oct 27
Total with taxes and fees
Bright & Cozy Chicago 1BR | Near Dining & Transit
A kitchen with open cabinets displaying cookware, plates, and mugs.

18. Workspace • Near Lakefront and Red Line • 6BR Apt

Workspace • Near Lakefront and Red Line • 6BR Apt
Rogers Park
5.4 out of 10, (3 reviews)
"My family of 6 adults and 3 children arrived at the property around 10:00 PM and were unable to enter using the access code that was provided. We repeatedly called and messaged the property manager but received no response for several hours. We weren’t able to get into the unit until around 3:00 AM, after the code was finally reset.We were traveling with children, so our only realistic options in the middle of the night were to sleep in the car or drive four hours back home. We ended up staying...
United States
Ngun C.
$507 nightly
The price is $595
Oct 19 - Oct 20
Total with taxes and fees
Workspace • Near Lakefront and Red Line • 6BR Apt
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.

19. Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
$224 nightly
The price is $250
Oct 26 - Oct 27
Total with taxes and fees
Comfortable 2BR Chicago Apt
Living area

20. Modern 4BR Rogers Park Stay Near Loyola

Modern 4BR Rogers Park Stay Near Loyola
Rogers Park
8.0 out of 10, Very good, (6 reviews)
"3 hours before we were supposed to check-in they canceled. They had my cell phone and didn't contact me. I had messaged them to get check in information and was only told at that time the place was now unavailable. For something as important as cancelling last minute they should have called, messaged and emailed. They had no problem requiring me via my cell phone to give them not only give them the names and ages of every guest staying but a picture of my passport and CC. Was this just a scam to...
United States
Stephanie K
$346 nightly
The price is $374
Oct 26 - Oct 27
Total with taxes and fees
Modern 4BR Rogers Park Stay Near Loyola
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

8/10 Good
"veru convenient for early flights from share."
arvind 1-night trip
Posted 3 hours ago
Hilton Chicago O'Hare Airport

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 $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

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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