Far North Side Vacation Rentals from $139: 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

Adrian

$221 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

2. Cozy studio in Andersonville Chicago

Edgewater

Katie K.

$113 nightly

Sep 8 - Sep 9

Total with taxes and fees

A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

3. Cozy apartment with AC and WiFi in awesome Chicago

Rogers Park

Kevin G.

$366 nightly

Aug 31 - Sep 1

Total with taxes and fees

A hotel room with a bed, a view of a cityscape, and a window with curtains.

4. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Uptown

Ryinne P.

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

5. The Lincoln Square Hideaway

Lincoln Square

Wendy T.

$342 nightly

Sep 22 - Sep 23

Total with taxes and fees

A dining table with a vase of white flowers, a bottle of wine, glasses, and a wooden board with strawberries and cheese.

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

Rogers Park

"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...

Joanna K.

$433 nightly

Aug 31 - Sep 1

Total with taxes and fees

A living room with a grey sofa, a round wooden coffee table, and a dining area with a wicker chair and a small table.

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

Uptown

Sheena T.

$376 nightly

Sep 27 - Sep 28

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.

8. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

O'Hare

Megan K.

$352 nightly

Aug 31 - Sep 1

Total with taxes and fees

9. 6BR Apt • Workspace • Near Lakefront + Red Line

Rogers Park

"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...

Ngun C.

$439 nightly

Aug 31 - Sep 1

Total with taxes and fees

10. 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

$325 nightly

Sep 1 - Sep 2

Total with taxes and fees

A modern living room with a sectional sofa, a round coffee table, and a floor lamp.

11. 2BR • Newly Furnished Modern Apt • Near O'Hare

O'Hare

$344 nightly

Sep 22 - Sep 23

Total with taxes and fees

A modern kitchen with white cabinetry, a central island, and a microwave above the stove.

12. Luxury King Bed • Remodeled Safe Chicago Condo

O'Hare

Lauren

$275 nightly

Aug 31 - Sep 1

Total with taxes and fees

A wooden board with cheese, strawberries, and olives on a table. A bottle of wine and a glass are also on the table.

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

O'Hare

David P.

$287 nightly

Sep 6 - Sep 7

Total with taxes and fees

A round dining table with a woven placemat, a rustic vase with green foliage, and a white chair.

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

O'Hare

15. 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

Collin M.

$642 nightly

Sep 8 - Sep 9

Total with taxes and fees

A modern apartment with a living room, kitchen, and a large window with curtains.

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

Uptown

flor

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

Rogers Park

Brande M.

$299 nightly

Sep 30 - Oct 1

Total with taxes and fees

A modern building with the name 'SENIORAL' prominently displayed on the facade.

18. Sentral Michigan Avenue

Downtown Chicago

Heather

$177 nightly

Aug 31 - Sep 1

Total with taxes and fees

19. Kasa Lake Shore Chicago

Downtown Chicago

Erica

$220 nightly

Sep 9 - Sep 10

Total with taxes and fees

A modern kitchen with a large island, bar stools, and a city view.

20. Level Chicago – Old Town

Downtown Chicago

Martha

$290 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Far North Side Hotel Reviews

River Hotel

10/10 Excellent

"Room was very clean and perfect for my needs. Check in and check out was so convenient and the staff was helpful when I needed to ask a question. The manager was so lovely and friendly, and the staff who assisted me at check in greeted me right away and was so personable, I believe his name was Pedro. Had an excellent experience overall and the location was very central to the things I wanted to do in the downtown area!"

Club Quarters Hotel, Central Loop, Chicago

8/10 Good

"We had a Nespresso machine in our room, but we didn't use it because the water vessel looked molded. I think the layout of the room could have been better. There was no end table for one side of the bed. the bathroom counter was not much of a counter. The highlight of the stay was the staff, specifically Adrian at the front desk. She gave us specific instructions about parking and when to scan our pass. She was so sweet and made us feel extremely welcome and called us her babies. We love Adrian soooo much."

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"The hotel was a bit older but had an excellent stay! Spacious rooms and cold ac. I would say the water isn't super hot if you're showering after someone but that isn't a deal breaker and it wasn't uncomfortable. Stayed here for a BTS show in Soldier Field and it was in a great location. Would stay here again for sure."

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 $139 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. Cozy apartment with AC and WiFi in awesome Chicago

4. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

5. The Lincoln Square Hideaway

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

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

8. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

9. 6BR Apt • Workspace • Near Lakefront + Red Line

10. Modern 4BR Rogers Park Stay Near Loyola

11. 2BR • Newly Furnished Modern Apt • Near O'Hare

12. Luxury King Bed • Remodeled Safe Chicago Condo

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

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

15. 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.

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

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

18. Sentral Michigan Avenue

19. Kasa Lake Shore Chicago

20. Level Chicago – Old Town

Find vacation rentals that suit your style

Top Far North Side Hotel Reviews

River Hotel

Find out more about Far North Side

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