Far North Side Vacation Rentals from $75: Search Short-Term Rentals

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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

Uptown

Michael S.

$219 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

2. Cozy studio in Andersonville Chicago

Edgewater

Sherry M.

$106 nightly

Dec 10 - Dec 11

Total with taxes and fees

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

Uptown

Paul J.

$217 nightly

Nov 17 - Nov 18

Total with taxes and fees

A living room with a flat-screen TV on a wooden cabinet, a dark sofa, a coffee table, a floor lamp, and a potted plant.

4. 1BR/1BA City Comfort

Lincoln Square

patricia r.

$145 nightly

Nov 16 - Nov 17

Total with taxes and fees

A bedroom with a bed, a nightstand, a desk, a chair, a ceiling fan, and a TV.

5. Sunny Studio in Heart of Ravenswood

Uptown

Patrick V.

$205 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

6. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

O'Hare

Megan K.

$385 nightly

Dec 1 - Dec 2

Total with taxes and fees

A modern living room with a black sofa, a wooden chair, a coffee table, and a dining area with a table and chairs.

7. Great Layout – Spacious 2BR Apt

Rogers Park

Eric C.

$186 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Rogers Park

Andrew O.

$252 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern living room with a dark blue sofa, a round coffee table with a vase of white flowers, a potted plant, and a framed picture of a horse on the wall.

9. 1BR Pad with Homey Feel

Lincoln Square

Dallas D.

$217 nightly

Nov 16 - Nov 17

Total with taxes and fees

A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

10. Chicago Riverhouse with private fenced in oasis

North Park

Robert S.

$515 nightly

Nov 19 - Nov 20

Total with taxes and fees

A modern kitchen with dark blue cabinets, stainless steel appliances, and a white countertop.

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

Uptown

$200 nightly

Dec 7 - Dec 8

Total with taxes and fees

A neatly made bed with a headboard, a bedside table, and a wall-mounted artwork of a bull.

12. Delightful 1BR Apt in Ravenswood

Uptown

"We had a nice stay and enjoyed our time here! The host was kind and very responsive, which we appreciated. We loved the location of this unit! It was very convenient for us. We had a minor issue checking in initially, The check-in info we were given to get into the unit was incorrect. It turned out it was for the wrong lock box. Thankfully the host (or an assistant/service rep) was quick to respond and help us. It was resolved within 15 minutes. The apartment itself was solid. It had all of the...

Tom P.

$217 nightly

Nov 17 - Nov 18

Total with taxes and fees

A covered porch with wicker furniture, a table, and a railing.

13. Spacious Chicago Group Home! Walk to Train & Eats

Uptown

Jeffrey K.

$621 nightly

Nov 16 - Nov 17

Total with taxes and fees

A kitchen with a granite countertop, stainless steel appliances, and white subway tiles.

14. Modern City Vibes | 1BR Stay

Rogers Park

$217 nightly

Nov 16 - Nov 17

Total with taxes and fees

A neatly made bed with white and mustard pillows, two framed artworks above it, and rolled towels on the bed.

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

North Park

$179 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a teal sofa, a round coffee table, a TV on a stand, a lamp, and a painting on the wall.

16. Stylish and Roomy 2BR in Chicago

Edgewater

$209 nightly

Nov 16 - Nov 17

Total with taxes and fees

A hotel room with a bed, bedside lamps, a painting, an air conditioning unit, and a window.

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

West Ridge

$201 nightly

Nov 16 - Nov 17

Total with taxes and fees

18. 1BR Serene and Cozy Chicago Apt!

Albany Park

Maximilian W.

$149 nightly

Nov 17 - Nov 18

Total with taxes and fees

19. Modern 4BR Rogers Park Stay Near Loyola

Rogers Park

"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...

Stephanie K

$311 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern living room with a green sectional sofa, a patterned rug, and artwork on the walls.

20. The Velvet Manor | 2BR Boutique Stay

Uptown

Nicole C.

$449 nightly

Nov 17 - Nov 18

Total with taxes and fees

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Top Far North Side Hotel Reviews

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"great location and very clean and spacious room."

Congress Plaza Hotel

8/10 Good

"This is an older hotel with a lot of rooms, so I am never sure what to expect -- but this was a good stay. We stored our bags at the beginning and end of our stay with no problems. Our room was in the north tower and it had been refurbished. Beds were comfortable enough, and it was clean even if some parts of the room (i.e. doors and windows) show their age. You can't beat the location for sightseeing and it's close to multiple L stations. For a Bears home game weekend, the room was the most reasonably priced I could find downtown. It will never be the nicest hotel in downtown Chicago, but it quite often offers the best value."

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 $75 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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Check prices for these dates

Our top choices for Far North Side vacation rentals

1. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

2. Cozy studio in Andersonville Chicago

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

4. 1BR/1BA City Comfort

5. Sunny Studio in Heart of Ravenswood

6. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

7. Great Layout – Spacious 2BR Apt

8. Cozy apartment with AC and WiFi in awesome Chicago

9. 1BR Pad with Homey Feel

10. Chicago Riverhouse with private fenced in oasis

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

12. Delightful 1BR Apt in Ravenswood

13. Spacious Chicago Group Home! Walk to Train & Eats

14. Modern City Vibes | 1BR Stay

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

16. Stylish and Roomy 2BR in Chicago

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

18. 1BR Serene and Cozy Chicago Apt!

19. Modern 4BR Rogers Park Stay Near Loyola

20. The Velvet Manor | 2BR Boutique Stay

Find vacation rentals that suit your style

Top Far North Side Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Find out more about Far North Side

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