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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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.
$118 nightly
The price is $145
Sep 8 - Sep 9
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
$221 nightly
The price is $266
Aug 24 - Aug 25
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
1 bedroom, desk, iron/ironing board, WiFi

3. 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.
$220 nightly
The price is $225
Aug 19 - Aug 20
Total with taxes and fees
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
6 bedrooms, desk, iron/ironing board, travel crib

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

6BR Apt • Workspace • Near Lakefront + Red Line
Rogers Park
6.0 out of 10, (2 reviews)
"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...
United States
Ngun C.
$436 nightly
The price is $511
Aug 19 - Aug 20
Total with taxes and fees
6BR Apt • Workspace • Near Lakefront + Red Line
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.
$246 nightly
The price is $291
Aug 19 - Aug 20
Total with taxes and fees
Mins from O'Hare • Safe Location • Private Parking
Microwave, oven, stovetop

6. 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.
$329 nightly
The price is $406
Sep 8 - Sep 9
Total with taxes and fees
Chic apartment with fitness room and AC in beautiful Chicago
TV, offices

7. Modern 4BR Rogers Park Stay Near Loyola

Modern 4BR Rogers Park Stay Near Loyola
Rogers Park
7.4 out of 10, Good, (3 reviews)
"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...
United States
Stephanie K
$336 nightly
The price is $362
Aug 19 - Aug 20
Total with taxes and fees
Modern 4BR Rogers Park Stay Near Loyola
Interior

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

Modern Condo • Safe Chicago Stay Near O’Hare
O'Hare
10.0 out of 10, Exceptional, (2 reviews)
"This VRBO was in great condition. Communication was excellent throughout our stay. Thanks"
United States
David P.
$264 nightly
The price is $312
Aug 20 - Aug 21
Total with taxes and fees
Modern Condo • Safe Chicago Stay Near O’Hare
Dining

9. 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)
"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.
$561 nightly
The price is $659
Sep 3 - Sep 4
Total with taxes and fees
Walk to the Beach • Private Office • 5BR
Smart TV, computer monitors

10. 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.
$370 nightly
The price is $437
Aug 31 - Sep 1
Total with taxes and fees
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
TV

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

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
$304 nightly
The price is $360
Sep 8 - Sep 9
Total with taxes and fees
2BR • Newly Furnished Modern Apt • Near O'Hare
Interior

12. 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
$221 nightly
The price is $266
Aug 20 - Aug 21
Total with taxes and fees
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Terrace/patio

13. 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, (26 reviews)
"Was a great and clean place to stay.. "
United States
Ashly B.
$260 nightly
The price is $313
Aug 23 - Aug 24
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
3 bedrooms, desk, iron/ironing board, WiFi (free)

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.

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
$649 nightly
The price is $727
Sep 8 - Sep 9
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.
Coffee/tea maker, fridge, microwave, oven

15. Luxury King Bed • Remodeled Safe Chicago Condo

Luxury King Bed • Remodeled Safe Chicago Condo
O'Hare
$286 nightly
The price is $338
Aug 24 - Aug 25
Total with taxes and fees
Luxury King Bed • Remodeled Safe Chicago Condo
Coffee/tea maker, fridge, microwave, oven

16. 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.
$364 nightly
The price is $449
Aug 19 - Aug 20
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
Exterior

17. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,271 reviews)
"Nice stay"
United States
Heather
$173 nightly
The price is $203
Sep 9 - Sep 10
Total with taxes and fees
Sentral Michigan Avenue
Lake

18. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (14 reviews)
"Great location and super clean!"
United States
Erica
$214 nightly
The price is $255
Sep 10 - Sep 11
Total with taxes and fees
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

19. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (518 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
$291 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
Level Chicago – Old Town
Interior

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

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
$327 nightly
The price is $404
Aug 20 - Aug 21
Total with taxes and fees
Cozy Studio Suite, Steps from River North & Shops
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

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"We were in the heart of downtown. The hotel is beautiful, the staff is kind and helpful. We enjoyed our stay. 10/10"
Amber 3-night trip
Posted 2 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop

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 $145 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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