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

Far North Side Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (93 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
$122 nightly
The price is $151
Oct 5 - Oct 6
Total with taxes and fees
Cozy studio in Andersonville Chicago
A rooftop terrace with a brick wall, large windows, and a metal railing.

2. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (27 reviews)
"Was a great and clean place to stay.. "
United States
Ashly B.
$223 nightly
The price is $268
Sep 23 - Sep 24
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A neatly made bed with folded towels, a bedside table with a lamp, a small plant, and a wall-mounted abstract painting.

3. 1BR Pad with Homey Feel

1BR Pad with Homey Feel
Lincoln Square
$212 nightly
The price is $229
Sep 29 - Sep 30
Total with taxes and fees
1BR Pad with Homey Feel
A living room with a flat-screen TV, a black sofa, a coffee table, and a ceiling fan.

4. Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
$208 nightly
The price is $231
Sep 21 - Sep 22
Total with taxes and fees
Cozy & Furnished 2BR Unit
A modern interior with a green sofa, a round wooden table, and large windows offering a view of greenery and buildings.

5. The Velvet Manor | 2BR Boutique Stay

The Velvet Manor | 2BR Boutique Stay
Uptown
$424 nightly
The price is $510
Sep 23 - Sep 24
Total with taxes and fees
The Velvet Manor | 2BR Boutique Stay
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

6. 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 near university, the lake and public transportation. Felt safe in this area. Room was as described but could certainly use some updates and maintenance."
United States
Kevin G.
$339 nightly
The price is $418
Oct 17 - Oct 18
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
A dining table with a vase of white flowers, a bottle of wine, glasses, and a wooden board with strawberries and cheese.

7. 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)
"This 5-bedroom Chicago apartment was an exceptional find for our group, offering a rare combination of ample space, safety, and convenience. The location is incredibly walkable and just a short distance from the beach, which made for wonderful morning walks and beautiful views. The neighborhood has a vibrant, welcoming atmosphere with a large student population, giving the area a lively yet entirely safe energy. One of the biggest highlights was the excellent, hassle-free parking, which is an...
United States
Joanna K.
$466 nightly
The price is $546
Sep 22 - Sep 23
Total with taxes and fees
Walk to the Beach • Private Office • 5BR
A modern kitchen with white cabinetry, a central island, and a microwave above the stove.

8. Luxury King Bed • Remodeled Safe Chicago Condo

Luxury King Bed • Remodeled Safe Chicago Condo
O'Hare
10.0 out of 10, Exceptional, (1 review)
"great place and location!"
United States
Lauren
$310 nightly
The price is $366
Sep 22 - Sep 23
Total with taxes and fees
Luxury King Bed • Remodeled Safe Chicago Condo
A modern living room with a sectional sofa, a round coffee table, and a floor lamp.

9. 2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
$318 nightly
The price is $376
Oct 14 - Oct 15
Total with taxes and fees
2BR • Newly Furnished Modern Apt • Near O'Hare
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.

10. 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, (4 reviews)
"The place was great overall and we really enjoyed our stay. The location and accommodations were nice, and everything was as expected. Unfortunately, there was no AC in the bedrooms, so the rooms got pretty hot at night, which made it a little uncomfortable for sleeping. Other than that, we had a great stay!"
United States
Kody T.
$394 nightly
The price is $465
Sep 29 - Sep 30
Total with taxes and fees
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

11. Modern 4BR Rogers Park Stay Near Loyola

Modern 4BR Rogers Park Stay Near Loyola
Rogers Park
7.4 out of 10, Good, (3 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
$367 nightly
The price is $398
Sep 21 - Sep 22
Total with taxes and fees
Modern 4BR Rogers Park Stay Near Loyola
A wooden board with cheese, strawberries, and olives on a table. A bottle of wine and a glass are also on the table.

12. Modern Condo • Safe Chicago Stay Near O’Hare

Modern Condo • Safe Chicago Stay Near O’Hare
O'Hare
8.0 out of 10, Very good, (3 reviews)
"This VRBO was in great condition. Communication was excellent throughout our stay. Thanks"
United States
David P.
$283 nightly
The price is $335
Sep 22 - Sep 23
Total with taxes and fees
Modern Condo • Safe Chicago Stay Near O’Hare
A compact kitchen with a microwave, stove, and oven.

13. Mins from O'Hare • Safe Location • Private Parking

Mins from O'Hare • Safe Location • Private Parking
O'Hare
8.0 out of 10, Very good, (2 reviews)
"I had no issues at all, they were in constant contact if i needed anything. The area was really nice and relaxing. Everything was 10 minutes or less drive. Truly a primed rental, would definitely go back"
United States
Daniel H.
$280 nightly
The price is $331
Sep 22 - Sep 23
Total with taxes and fees
Mins from O'Hare • Safe Location • Private Parking
A modern living room with a large plant, a dining area with a wooden table, and a white sofa.

14. Modern 1BR w/ Workspace near O'Hare

Modern 1BR w/ Workspace near O'Hare
O'Hare
$250 nightly
The price is $295
Sep 28 - Sep 29
Total with taxes and fees
Modern 1BR w/ Workspace near O'Hare
A hotel room with a bed, a view of a cityscape, and a window with curtains.

15. 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.
$217 nightly
The price is $222
Sep 22 - Sep 23
Total with taxes and fees
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

16. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (44 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
$601 nightly
The price is $698
Oct 8 - Oct 9
Total with taxes and fees
Chicago Riverhouse with private fenced in oasis
A modern bedroom with a bed, bedside table, and a mirror.

17. 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.
$617 nightly
The price is $730
Oct 5 - Oct 6
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 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.
$302 nightly
The price is $372
Oct 17 - Oct 18
Total with taxes and fees
Chic apartment with fitness room and AC in beautiful Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

19. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,322 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
$177 nightly
The price is $208
Sep 27 - Sep 28
Total with taxes and fees
Sentral Michigan Avenue

20. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (31 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
$191 nightly
The price is $227
Sep 27 - Sep 28
Total with taxes and fees
Kasa Lake Shore Chicago
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 Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Clean room, great location!"
Rohit 2-night trip
Posted less than an hour ago
The Royal Sonesta Chicago Downtown

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 $151 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.

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