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

Far North Side Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Far North Side vacation rentals

1 bedroom, iron/ironing board, WiFi (free), bed sheets

1. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (89 reviews)
"It was small and cozy and perfect for a weekend trip in Chicago"
United States
Lilly L.
$149 nightly
The price is $184
Aug 25 - Aug 26
Total with taxes and fees
Cozy studio in Andersonville Chicago
Terrace/patio

2. 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, (58 reviews)
"So hospitable "
United States
Adrian
$278 nightly
The price is $335
Aug 3 - Aug 4
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Dining

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

Walk to the Beach • Private Office • 5BR
Rogers Park
7.8 out of 10, Good, (10 reviews)
"Very spacious, with an amazing layout that offers privacy in individual rooms yet also multiple family gathering spaces. Lovely furnishings & everything you need to cook or dine in. I never leave home without my own sheets but i was uncharacteristically comfortable sleeping on their bedding, which were very clean & well maintained. Well appointed with giant TVs set up for streaming in every room! Quick walk to public transit & close to the top of Lakeshore Drive - lots of local options too, and...
United States
Amy R.
$566 nightly
The price is $664
Aug 17 - Aug 18
Total with taxes and fees
Walk to the Beach • Private Office • 5BR
1 bedroom, desk, iron/ironing board, WiFi

4. 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.
$325 nightly
The price is $334
Aug 6 - Aug 7
Total with taxes and fees
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Coffee/tea maker, fridge, microwave, oven

5. 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.
$238 nightly
The price is $281
Aug 4 - Aug 5
Total with taxes and fees
Mins from O'Hare • Safe Location • Private Parking
Interior

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

Modern Condo • Safe Chicago Stay Near O’Hare
O'Hare
10.0 out of 10, Exceptional, (1 review)
"The overall experience was fantastic. The unit was clean and well stocked to meet all my needs for the stay. Staff were very responsive and helpful with all inquires"
United States
Jatin P.
$240 nightly
The price is $284
Aug 3 - Aug 4
Total with taxes and fees
Modern Condo • Safe Chicago Stay Near O’Hare
Microwave, oven, stovetop

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

Chic apartment with fitness room and AC in beautiful Chicago
Rogers Park
5.8 out of 10, (6 reviews)
"Everything was smooth and efficient "
United States
Brande M.
$329 nightly
The price is $406
Aug 18 - Aug 19
Total with taxes and fees
Chic apartment with fitness room and AC in beautiful Chicago
Smart TV, computer monitors

8. 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, (2 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.
$441 nightly
The price is $521
Aug 25 - Aug 26
Total with taxes and fees
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
Dining

9. 1BR Near O'Hare • Balcony • Workspace

1BR Near O'Hare • Balcony • Workspace
O'Hare
$264 nightly
The price is $312
Aug 5 - Aug 6
Total with taxes and fees
1BR Near O'Hare • Balcony • Workspace
TV

10. 2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
$328 nightly
The price is $388
Aug 12 - Aug 13
Total with taxes and fees
2BR • Newly Furnished Modern Apt • Near O'Hare
Beach

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

W2 - ❤️ New and Clean! Big Apartment with Parking
Uptown
10.0 out of 10, Exceptional, (69 reviews)
"Enjoyed our stay. Great value, convenient and roomy. Will be staying here upon our return. "
United States
Danny B.
$420 nightly
The price is $502
Aug 11 - Aug 12
Total with taxes and fees
W2 - ❤️ New and Clean! Big Apartment with Parking
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

12. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (22 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.
$571 nightly
The price is $703
Aug 2 - Aug 3
Total with taxes and fees
The Lincoln Square Hideaway
Interior

13. 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, (18 reviews)
"I don’t know if I recommend that place! ends up charging fees that make the total cost much higher than the nightly room rate."
United States
flor
$224 nightly
The price is $270
Aug 10 - Aug 11
Total with taxes and fees
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Books, computer monitors

14. Clark and Balmoral

Clark and Balmoral
Edgewater
10.0 out of 10, Exceptional, (7 reviews)
"Great place to stay. Amazing location, quiet, yet close to all Andersonville has to offer- great restaurants, shopping, and a fun vibe. The beds and pillows were super comfortable, fully stocked kitchen, including reusable bags for grocery shopping (saves you a few cents in bag fees)."
United States
Carie L.
$525 nightly
The price is $628
Aug 17 - Aug 18
Total with taxes and fees
Clark and Balmoral
Smart TV, fireplace

15. This 2 bedroom 2 bathroom elegantly furnished home is ready for all your needs. Featuring a primary bedroom suite, TV room, dining room, and additional sitting areas.

This 2 bedroom 2 bathroom elegantly furnished home is ready for all your needs. Featuring a primary bedroom suite, TV room, dining room, and additional sitting areas.
Rogers Park
10.0 out of 10, Exceptional, (15 reviews)
"Great location, quiet, lovely apartment "
United States
Tera F.
$588 nightly
The price is $768
Aug 18 - Aug 19
Total with taxes and fees
This 2 bedroom 2 bathroom elegantly furnished home is ready for all your needs. Featuring a primary bedroom suite, TV room, dining room, and additional sitting areas.
Coffee/tea maker, fridge, microwave, oven

16. Luxury King Bed • Remodeled Safe Chicago Condo

Luxury King Bed • Remodeled Safe Chicago Condo
O'Hare
$313 nightly
The price is $370
Aug 10 - Aug 11
Total with taxes and fees
Luxury King Bed • Remodeled Safe Chicago Condo
Terrace/patio

17. 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, (23 reviews)
"Was a great and clean place to stay.. "
United States
Ashly B.
$252 nightly
The price is $303
Aug 23 - Aug 24
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Coffee/tea maker, fridge, microwave, oven

18. Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.8 out of 10, Good, (13 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
$361 nightly
The price is $445
Aug 2 - Aug 3
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
Smart TV, computer monitors

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

Modern 1BR w/ Workspace near O'Hare
O'Hare
$258 nightly
The price is $305
Aug 11 - Aug 12
Total with taxes and fees
Modern 1BR w/ Workspace near O'Hare
Indoor pool

20. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,234 reviews)
"Great property and location."
United States
Michael
$176 nightly
The price is $207
Aug 30 - Aug 31
Total with taxes and fees
Sentral Michigan Avenue
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Far North Side Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"You have to pay additional to have access to the sky lounge deck and gym. First time I stayed at a hotel that would charge extra. No pool if you interested in it."
Petrina 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

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 $184 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.

Explore a world of travel with Expedia