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 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

Interior

1. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (19 reviews)
"Perfect uptown location. Host was very responsive. "
United States
Christopher S.
$308 nightly
The price is $370
Sep 17 - Sep 18
Total with taxes and fees
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Smart TV

2. W3 - Spacious 2BR Apt + Free On-site Parking

W3 - Spacious 2BR Apt + Free On-site Parking
Uptown
10.0 out of 10, Exceptional, (72 reviews)
"We had a wonderful stay and the host was pleasesnt and easy to communicate with. We’d definitely stay here again :)"
United Kingdom
Sheena T.
W3 - Spacious 2BR Apt + Free On-site Parking
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

3. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (25 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.
$341 nightly
The price is $420
Sep 22 - Sep 23
Total with taxes and fees
The Lincoln Square Hideaway
1 bedroom, iron/ironing board, WiFi (free), bed sheets

4. 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
Coffee/tea maker, fridge, microwave, oven

5. 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.
$341 nightly
The price is $421
Oct 15 - Oct 16
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
Beach

6. W2 - ❤️ New and Clean! Big Apartment with Parking

W2 - ❤️ New and Clean! Big Apartment with Parking
Uptown
10.0 out of 10, Exceptional, (71 reviews)
"Great location and apartment had everything we needed!"
United States
Misty M.
W2 - ❤️ New and Clean! Big Apartment with Parking
Outdoor dining

7. 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
Dining

8. 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.
$475 nightly
The price is $557
Sep 22 - Sep 23
Total with taxes and fees
Walk to the Beach • Private Office • 5BR
3 bedrooms, desk, iron/ironing board, travel crib

9. 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.
$616 nightly
The price is $729
Sep 23 - Sep 24
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.
Interior

10. 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
Smart TV, computer monitors

11. 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 $466
Oct 6 - Oct 7
Total with taxes and fees
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
Coffee/tea maker, fridge, microwave, oven

12. 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.
$293 nightly
The price is $346
Sep 22 - Sep 23
Total with taxes and fees
Mins from O'Hare • Safe Location • Private Parking
Coffee/tea maker, fridge, microwave, oven

13. 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
$311 nightly
The price is $367
Sep 22 - Sep 23
Total with taxes and fees
Luxury King Bed • Remodeled Safe Chicago Condo
Dining

14. 1BR Near O'Hare • Balcony • Workspace

1BR Near O'Hare • Balcony • Workspace
O'Hare
$285 nightly
The price is $336
Sep 21 - Sep 22
Total with taxes and fees
1BR Near O'Hare • Balcony • Workspace
TV

15. 2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
$319 nightly
The price is $377
Oct 14 - Oct 15
Total with taxes and fees
2BR • Newly Furnished Modern Apt • Near O'Hare
Interior

16. 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.
$287 nightly
The price is $340
Sep 21 - Sep 22
Total with taxes and fees
Modern Condo • Safe Chicago Stay Near O’Hare
Microwave, oven, stovetop

17. 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
Smart TV, computer monitors

18. 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
Lake

19. 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
$245 nightly
The price is $291
Sep 20 - Sep 21
Total with taxes and fees
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

20. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (524 reviews)
"Location and facility was very nice"
United States
Brian
$364 nightly
The price is $428
Sep 27 - Sep 28
Total with taxes and fees
Level Chicago – Old Town
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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Comfortable and aesthetic! Enjoyed our stay a lot."
Ryan 4-night trip
Posted less than an hour ago
InterContinental Chicago Magnificent Mile by IHG

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.

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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