Far North Side Vacation Rentals from $151: Search Short-Term Rentals

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Our top choices for Far North Side vacation rentals

1. Cozy studio in Andersonville Chicago

Edgewater

Lilly L.

$122 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Uptown

Adrian

$225 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

Uptown

Ryinne P.

$365 nightly

Sep 13 - Sep 14

Total with taxes and fees

4. 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 24 - Aug 25

Total with taxes and fees

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

O'Hare

Daniel H.

$241 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

Rogers Park

Brande M.

$280 nightly

Aug 23 - Aug 24

Total with taxes and fees

7. 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

$347 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

O'Hare

David P.

$237 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

Rogers Park

"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...

Amy R.

$607 nightly

Sep 3 - Sep 4

Total with taxes and fees

10. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

O'Hare

Megan K.

$360 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

O'Hare

$312 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Uptown

flor

$232 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Uptown

Ashly B.

$225 nightly

Aug 23 - Aug 24

Total with taxes and fees

14. 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.

$560 nightly

Sep 8 - Sep 9

Total with taxes and fees

15. Luxury King Bed • Remodeled Safe Chicago Condo

O'Hare

Lauren

$271 nightly

Aug 23 - Aug 24

Total with taxes and fees

16. Cozy apartment with AC and WiFi in awesome Chicago

Rogers Park

John D.

$252 nightly

Aug 23 - Aug 24

Total with taxes and fees

17. Sentral Michigan Avenue

Downtown Chicago

Heather

$173 nightly

Sep 8 - Sep 9

Total with taxes and fees

18. Kasa Lake Shore Chicago

Downtown Chicago

Erica

$231 nightly

Sep 9 - Sep 10

Total with taxes and fees

19. Level Chicago – Old Town

Downtown Chicago

Martha

$289 nightly

Aug 31 - Sep 1

Total with taxes and fees

20. Cozy Studio Suite, Steps from River North & Shops

Near North Side

Susannah R.

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Top Far North Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

8/10 Good

"Staff was outstanding and location was perfect for visiting UIC"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"This is an amazing hotel in the heart of Chicago. Highly recommended. I got an upgrade for a huge room apartment style with river and downtown view. Room was quiet and clean. The staff is very friendly and helpful. The hotel is conveniently located close to many attractions within walking distance. And public transportation is nearby. I did not need a rental or a taxi."

Hotel Riu Plaza Chicago

8/10 Good

"They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun."

Congress Plaza Hotel

10/10 Excellent

"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests throughout it's time. We are already planning our next trip back to Chicago and will likely stay here again! Highly recommend staying here!"

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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Room 1

Check prices for these dates

Our top choices for Far North Side vacation rentals

1. Cozy studio in Andersonville Chicago

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

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

4. 6BR Apt • Workspace • Near Lakefront + Red Line

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

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

7. Modern 4BR Rogers Park Stay Near Loyola

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

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

10. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

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

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

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

14. 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.

15. Luxury King Bed • Remodeled Safe Chicago Condo

16. Cozy apartment with AC and WiFi in awesome Chicago

17. Sentral Michigan Avenue

18. Kasa Lake Shore Chicago

19. Level Chicago – Old Town

20. Cozy Studio Suite, Steps from River North & Shops

Find vacation rentals that suit your style

Top Far North Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

The Royal Sonesta Chicago Downtown

Fairmont Chicago at Millennium Park

Hotel Riu Plaza Chicago

L7 Chicago by LOTTE

InterContinental Chicago Magnificent Mile by IHG

Congress Plaza Hotel

Club Quarters Hotel, Central Loop, Chicago

Kasa Magnificent Mile Chicago

Find out more about Far North Side

Explore a world of travel with Expedia

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