Title: North Side Vacation Home Rentals from CA $258: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[North Side Travel Guide](https://expedia.ca/North-Side.dx553248635976475406)[Hotels in North Side](https://expedia.ca/North-Side-Hotels.d553248635976475406.Travel-Guide-Hotels)[Vacation Rentals in North Side](https://expedia.ca/North-Side-Vacation-Rentals.d553248635976475406.Travel-Guide-VacationRentals)[Flights to North Side](https://expedia.ca/Cheap-Flights-To-North-Side.d553248635976475406.Travel-Guide-Flights)[Things to do in North Side](https://expedia.ca/Things-To-Do-In-North-Side.d553248635976475406.Travel-Guide-Activities)[North Side Car Rentals](https://expedia.ca/Car-Rentals-In-North-Side.d553248635976475406.Car-Rental-Guide)[North Side Vacation Packages](https://expedia.ca/North-Side.d553248635976475406.Destination-Travel-Guides)

![Lincoln Park Conservatory featuring a park](https://images.trvl-media.com/place/6065145/be972840-8e65-4d67-9b9c-b38267f694ab.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# North Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select North Side Vacation Homes

![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/c092839a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/abefe3c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/ac2274d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, dishwasher, coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/f344797b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Wrigley Field! Townhouse w/ Pool Table

Lakeview

CA $195

CA $879 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Wrigley-Field-Townhouse-W-Pool-Table.h122662962.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/5ccfbbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/f18fcae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Robertsdale

9.8/10

Exceptional

(15)

"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen D.

CA $200

CA $279 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/61fb0165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/3a6b662e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Master qtr close to nature & easy urban facilities

Riverwoods

9.8/10

Exceptional

(73)

"Perfect secluded neighborhood. Very quiet which is what we needed to just get away from everything. Shopping and restaurants are all within 10 minutes. Owner always answered my questions right away. Would stay there again for a little retreat."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Timothy

CA $125

CA $258 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/a0f5c46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/1dc70e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/c1640248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/49bef28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*The Comfy King Ranch\*King Bed Suite\*Fast Wi-Fi

Worth

9.6/10

Exceptional

(53)

"Perfect place for an 8 person golf trip! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Griffin P.

CA $217

CA $463 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w867h654x78y17-d683a7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/9878af78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w506h683x260y0-79a3d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w904h683x60y0-33f7d28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coziest estate home 20 minutes to downtown

Willow Springs

8.8/10

Excellent

(15)

"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gabriela N.

CA $252

CA $556 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Coziest-Estate-Home-20-Minutes-To-Downtown.h88494875.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/c4f6c687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/699d0fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/3f6e4959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vintage Urban Retreat

Oak Park

10/10

Exceptional

(12)

"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas P.

CA $192

CA $646 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/24b80113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/d13cd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/58bc029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/df397b69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Getaway Near ORD With Great Local Amenities

Des Plaines

9.0/10

Wonderful

(4)

"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie G.

[](https://www.expedia.ca/Chicago-Hotels-Getaway-Near-ORD-With-Great-Local-Amenities.h89818126.Hotel-Information)

![Fitness facility](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/c9a94206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/6b52890f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/2246e8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/33260724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Theater • Game Room • Gym • Firepit • 4BR Home

Belmont Cragin

CA $133

CA $770 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Chicago-Hotels-Theater-Game-Room-Gym-Firepit-4BR-Home.h122811987.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/e376d974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/dc90b17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/b132ab29_edited_0386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/08f64820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

7.8/10

Good

(15)

"Very nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elliot H.

CA $208

CA $339 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/1e6ca815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/ccf123af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/5ff1a0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/w2874h1613x0y1-952d9d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

8.8/10

Excellent

(38)

"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott C.

CA $220

CA $476 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/7407c2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/cb5bf3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/c8a15818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/4c4c570d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Victorian Vibes ❤️ | Character & Charm

Oak Park

10/10

Exceptional

(26)

"Great location and walkable to restaurants. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura B.

CA $216

CA $677 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/696abe25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/6b638712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/37f6160a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/7bc6fa05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale

10/10

Exceptional

(17)

"Great property and great host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Darin H.

CA $251

CA $551 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h71947955.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/71fea1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/340d0fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/643f9b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/29e8ad65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enamored in Elmhurst

Elmhurst

10/10

Exceptional

(13)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aaron B.

CA $297

CA $695 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Enamored-In-Elmhurst.h105783565.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/w1179h800x21y0-c9fb8097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/24a188f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/db12f84a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/45b3ad33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 4BR Retreat Near MDW | LCP Collection

Burbank

9.4/10

Exceptional

(6)

"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie S.

CA $257

CA $640 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Modern-4BR-Retreat-Near-MDW-LCP-Collection.h99269654.Hotel-Information)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/1b5edb97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/2b52d153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/9defe80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/d229b52f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

CA $197

CA $575 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121303866.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/b84b8d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/323d116b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1019h683x3y0-935e50e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1017h683x4y0-e81f9176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Lombard

9.6/10

Exceptional

(16)

"I had a great stay over the weekend with my family it was very relaxing and peaceful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tennika W.

CA $225

CA $466 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-Comfy-Home-W-Access-To-Major-RoadsHwys.h84314776.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/119000000/118370000/118370000/118369993/78822509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118370000/118370000/118369993/83863909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118370000/118370000/118369993/6fbaf3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118370000/118370000/118369993/00bbdec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Main St Hideaway: Near Lee Street Beach: Northwestern University: Transit

South Evanston

CA $186

CA $468 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Chicago-Hotels-Charming-1-Bedroom-Cottage-Lee-Street-Beach.h118369993.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/17cec5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/f24571b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/2f690fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, video library](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/e7f5fdcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Skokie

10/10

Exceptional

(34)

"Great place to congregate with family and a pet. Lots of room to gather."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leone W.

CA $415

CA $923 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Luxe-Haus-Of-LoveRenovated-1938-Cape-Cod-Heated-FLRS.h89733678.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975504/73d8397c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975504/w903h683x60y0-ad409099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975504/w905h683x59y0-b649534e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975504/w906h683x59y0-d320854b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhome with Game Zone, Big Beds, & Smart TVs

Westmont

CA $205

CA $604 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-Townhome-With-Game-Zone.h117975504.Hotel-Information)

![Microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/e3c24e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/1c5af541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/95d8c884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/9a52aa75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Villa Park

10/10

Exceptional

(1)

"Great location and perfect set up for a family size Vaca!! Loved it!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robin C.

CA $264

CA $634 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Chicago-Hotels-Charming-3BR2BA-Retreat-In-Villa-Park-Comfort.h117840012.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-12-16&endDate=2025-12-17&regionId=553248635976475406&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248635976475406)

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FNorth-Side-Private-Vacation-Homes.d553248635976475406-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNorth-Side-Private-Vacation-Homes.d553248635976475406-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top North Side Hotel Reviews

![Hotel Lincoln](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/48b7272b_y.jpg)

### Hotel Lincoln

10/10 Excellent

"Staff who checked us in was great-very friendly. Room was pretty nice, but right between the elevators."

[](https://expedia.ca/Chicago-Hotels-Hotel-Lincoln.h23314.Hotel-Information)

![City Suites Hotel](https://images.trvl-media.com/lodging/1000000/900000/892700/892669/2966b348_y.jpg)

### City Suites Hotel

10/10 Excellent

"Nice hotel outside of the busy CBD. We picked this hotel due to its location. Having the train line right next door made traveling to/from the airport and checking out the city very convenient. The room was small but clean. We did not get the room upgrade we hoped for. Lots of great restaurants around. The hotel is older but I found it charming!"

[](https://expedia.ca/Chicago-Hotels-City-Suites-Hotel.h892669.Hotel-Information)

![Ray's Bucktown B&B](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/67423b1d_y.jpg)

### Ray's Bucktown B&B

10/10 Excellent

"Ray’s B&B is triple-A accommodations… Authentic, Amazing, & Artistic. Inviting and helpful staff, delicious food cooked-to-order (don’t skip), & an unending supply of things to look at in a great neighborhood will guarantee you have a great stay!"

[](https://expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information)

![The Villa Toscana](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/a7524278_y.jpg)

### The Villa Toscana

10/10 Excellent

"Will definitely stay here again. "

[](https://expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information)

![Hotel Zachary Chicago, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/24000000/23060000/23056000/23055991/030ea101_y.jpg)

### Hotel Zachary Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"I travel for work often, to many states, and Hotel Zachary is my absolute, hands down favorite hotel I have stayed at anywhere in the country. The staff is ALWAYS super friendly and helpful, truly exceptional.!! Also, the location is awesome! Stayed many times and never had a bad experience!!"

[](https://expedia.ca/Chicago-Hotels-Hotel-Zachary-Chicago.h23055991.Hotel-Information)

![Dorothy's](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/f61e991e_y.jpg)

### Dorothy's

10/10 Excellent

"so convenient, cozy, and welcoming. excellent"

[](https://expedia.ca/Chicago-Hotels-Dorothys.h108573352.Hotel-Information)

![Hotel Versey Chicago Lincoln Park](https://images.trvl-media.com/lodging/1000000/30000/23000/22993/64a1c63a_y.jpg)

### Hotel Versey Chicago Lincoln Park

10/10 Excellent

"Amazing staff. Comfy room"

[](https://expedia.ca/Chicago-Hotels-Hotel-Versey-Chicago-Lincoln-Park.h22993.Hotel-Information)

![Best Western Plus Hawthorne Terrace Hotel](https://images.trvl-media.com/lodging/1000000/120000/116900/116850/76dfc5de_y.jpg)

### Best Western Plus Hawthorne Terrace Hotel

10/10 Excellent

"Everything was great. All staff was there was friendly and courteous. "

[](https://expedia.ca/Chicago-Hotels-Best-Western-Plus-Hawthorne-Terrace-Hotel.h116850.Hotel-Information)

![The Majestic Hotel](https://images.trvl-media.com/lodging/1000000/10000/7200/7127/bf9d41f0_y.jpg)

### The Majestic Hotel

10/10 Excellent

"Ameila was super amazing at the front desk, the room was amazing and the walkability was perfect."

[](https://expedia.ca/Chicago-Hotels-The-Majestic-Hotel.h7127.Hotel-Information)

## Find out more about North Side

## North Side Vacation Homes information

| Number of reviews | 330 |
| --- | --- |
| Accommodation | 78 Vacation Homes |
| Lowest Price | CA $258 |
| Highest Price | CA $963 |

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-   [Hotels with Waterslides in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-Hotels-With-Waterslides.0-n6338684-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels)
-   [Lgbt Friendly Hotels in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6338684-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Lake Hotels in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-Lake-Hotels.0-n6338684-0-tLakeHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-Luxury-Hotel.0-n6338684-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-Oceanfront-Hotels.0-n6338684-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-Pet-Friendly-Hotel.0-n6338684-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Shopping Hotels in Wrigleyville](https://www.expedia.ca/Wrigleyville-Chicago-Hotels-Shopping-Hotel.0-n6338684-0-tShoppingHotel.Travel-Guide-Filter-Hotels)
-   [Wrigleyville Hotels](https://www.expedia.ca/Wrigleyville-Chicago-Hotels.0-n6338684-0.Travel-Guide-Filter-Hotels)

-   [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
-   [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

-   [Visit Bucktown](https://www.expedia.ca/Chicago-Bucktown.dx553248622905536905)
-   [Visit Lakeview](https://www.expedia.ca/Chicago-Lakeview.dx178166)
-   [Visit Roscoe Village](https://www.expedia.ca/Chicago-Roscoe-Village.dx553248635939578987)
-   [Lakeview Vacations](https://www.expedia.ca/Lakeview.d178166.Destination-Travel-Guides)
-   [Wrigley Field](https://www.expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

-   [Car rentals near Lakeview](https://www.expedia.ca/Car-Rentals-In-Lakeview.d178166.Car-Rental-Guide)

-   [Book Vacation Homes in North Side on Expedia.com](https://www.expedia.com/North-Side-Private-Vacation-Homes.d553248635976475406-aaPrivateVacationHomes.Travel-Guide-Accommodation)