Title: North Side Vacation Home Rentals from CA $219: 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)

![Great view of the city at Christmas time they light up the zoo. It's a great thing to do during the holidays
#URBANJUNGLE](https://images.trvl-media.com/place/829/f6594aff-9bbe-4eff-8e85-1343b34d50f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Vincent Ramundo

![](https://images.trvl-media.com/place/829/f6594aff-9bbe-4eff-8e85-1343b34d50f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for North Side vacation homes

![Interior](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/139d9ee8.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/d880898a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/928e7842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/bb724005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lakeview

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

CA $170

CA $836 total

includes taxes & fees

Jan 25 - Jan 26

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124380000/124377800/124377777/89656521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124380000/124377800/124377777/b84207ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/125000000/124380000/124377800/124377777/3aa2184d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/125000000/124380000/124377800/124377777/bdb92937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-9BR-Luxurious-Wrigleyville-Deco-House-Sleeps-20.h124377777.Hotel-Information)

CA $624

CA $2,461 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Chicago-Hotels-9BR-Luxurious-Wrigleyville-Deco-House-Sleeps-20.h124377777.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e3fd1233.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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/da25d2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Robertsdale

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

9.8/10

Exceptional

(20 reviews)

"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 $148

CA $219 total

includes taxes & fees

Jan 26 - Jan 27

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

![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/699e81d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/64fce148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/d1a40a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

[](https://www.expedia.ca/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information)

9.8/10

Exceptional

(33 reviews)

"great stay"

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

matt R.

CA $80

CA $267 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d658c7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/3081c65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/a541fdcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/3eea93c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information)

10/10

Exceptional

(1 review)

"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."

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

Willow M.

CA $215

CA $417 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.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)

![Interior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/ca60baaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/d81d6c50.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)

### Vacation Home in Riverwoods

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

9.8/10

Exceptional

(76 reviews)

"Nice , private and peaceful definitely will be back "

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

BRANDEN J.

CA $135

CA $270 total

includes taxes & fees

Jan 26 - Jan 27

[](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/72000000/71680000/71677300/71677273/7b6dc406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/5569ce20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/932d3e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/26045e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Worth

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

9.6/10

Exceptional

(55 reviews)

"Very clean and comfortable! Great place for our short stay! So much space it was great!"

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

David L.

CA $221

CA $470 total

includes taxes & fees

Jan 25 - Jan 26

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

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-5a95ad03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-2c40f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1433h1080x93y0-253226e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-7ee1aa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Shore

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information)

CA $29

CA $593 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w905h683x59y0-1e5c290a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w906h683x59y0-58db832b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w756h683x134y0-73459ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w903h683x61y0-6bb2c68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in La Grange Highlands

[](https://www.expedia.ca/Chicago-Hotels-Guesthouse-Gem-2BR.h117975506.Hotel-Information)

10/10

Exceptional

(4 reviews)

"very professional hosts and warm accommodations thank you!"

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

Shawn T.

CA $116

CA $351 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Guesthouse-Gem-2BR.h117975506.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/e7e36576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/d590570a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/c88a9d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/7e3db215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Humboldt Park

[](https://www.expedia.ca/Chicago-Hotels-Gated-Family-Home-W-Chefs-Kitchen.h122731919.Hotel-Information)

CA $175

CA $660 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Chicago-Hotels-Gated-Family-Home-W-Chefs-Kitchen.h122731919.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/b80be72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x60y0-4a286511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w906h683x59y0-ad8ac03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w903h683x60y0-a4b1b07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westchester

[](https://www.expedia.ca/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information)

9.8/10

Exceptional

(19 reviews)

"Great place Great location "

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

Josh W.

CA $206

CA $563 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/afb1f08b.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)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/d36efedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/d127a41d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Maywood

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

8.0/10

Very good

(21 reviews)

"Very nice place "

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

Elliot H.

CA $205

CA $420 total

includes taxes & fees

Jan 26 - Jan 27

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

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.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)

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

### Vacation Home in Oak Park

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

10/10

Exceptional

(14 reviews)

"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 $217

CA $681 total

includes taxes & fees

Jan 26 - Jan 27

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w903h683x60y0-f205b528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w905h683x60y0-d3c62524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w904h683x60y0-92c8079f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w908h683x58y0-0a2075c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westmont

[](https://www.expedia.ca/Chicago-Hotels-Back-Unit-Patio.h120544690.Hotel-Information)

CA $148

CA $386 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Back-Unit-Patio.h120544690.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/acc33991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/121a5c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/fba7b9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/337409c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Portage Park

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.Hotel-Information)

CA $179

CA $1,179 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/ec2f705b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/147fbb73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/c237f0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/6304a47a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Glen Ellyn

[](https://www.expedia.ca/Chicago-Hotels-Luxury-Suite-In-Glen-Ellyn.h96832141.Hotel-Information)

9.6/10

Exceptional

(10 reviews)

"Was very comfortable. Had everything we needed except wash clothes. Walmart really close. "

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

Debra B.

CA $219

CA $472 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Luxury-Suite-In-Glen-Ellyn.h96832141.Hotel-Information)

![Smart TV, fireplace, books, video library](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/374225f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/4ec2f70e.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/da6361a8.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/90000000/89740000/89733700/89733678/82099dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Skokie

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

10/10

Exceptional

(34 reviews)

"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "

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

carlos l.

CA $412

CA $924 total

includes taxes & fees

Jan 26 - Jan 27

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

![Dining](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/baf1fbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/f7e53c4b.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/97000000/96390000/96384200/96384152/02ca8784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in Elmhurst

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

8.8/10

Excellent

(39 reviews)

"Great place to stay. Plenty of backyard space. "

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

Terrence M.

CA $186

CA $437 total

includes taxes & fees

Jan 26 - Jan 27

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

![Exterior detail](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/793bb6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/e028cf83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/94169926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/0900c857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

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

10/10

Exceptional

(28 reviews)

"Great location and walkable to restaurants. "

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

Laura B.

CA $242

CA $711 total

includes taxes & fees

Jan 25 - Jan 26

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

![Interior](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/89651141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/e14752ef.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)

![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1018h683x3y0-7ed1e010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lombard

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

9.6/10

Exceptional

(17 reviews)

"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 $171

CA $415 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Comfy-Home-W-Access-To-Major-RoadsHwys.h84314776.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=2026-02-06&endDate=2026-02-07&regionId=553248635976475406&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cottages

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Villas

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Condos

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=North+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475406&latLong=41.933522%2C-87.677589&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=VACATION_HOME)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=North+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475406&latLong=41.933522%2C-87.677589&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=RESIDENCE)

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## Top North Side Hotel Reviews

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

### The Majestic Hotel

10/10 Excellent

"Very clean"

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

![The Chicago Hotel Collection - Wrigleyville](https://images.trvl-media.com/lodging/24000000/23610000/23604900/23604891/582f9da7_y.jpg)

### The Chicago Hotel Collection - Wrigleyville

10/10 Excellent

"Upon entering the baseball motif was amazing. The room was exactly as shown in the pictures and was even more impressive by how quiet and how close everything was to the location. Only draw back was no parking on the property. Extra expense to park in the parking garage down the street. Hotel staff was amazing and the property was very secure and clean. Would really recommend staying here. "

[](https://expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Wrigleyville.h23604891.Hotel-Information)

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

### Hotel Lincoln

10/10 Excellent

"We enjoyed our stay! It was very close to where our daughter lives and very walkable and accessible to everything!"

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

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

### Dorothy's

10/10 Excellent

"cozy and close to cool places"

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

![The Hotel at Midtown](https://images.trvl-media.com/lodging/19000000/18390000/18385300/18385274/30af6beb_y.jpg)

### The Hotel at Midtown

10/10 Excellent

"Easy to get last minute reservation and check in/out"

[](https://expedia.ca/Chicago-Hotels-The-Hotel-At-Midtown.h18385274.Hotel-Information)

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

### City Suites Hotel

10/10 Excellent

"I love the location and it’s next to the Brown-Red-Purple Lines El Station. It’s is well kept “Historical” property. It’s is quite quaint and charming. Food sources abound within easy walking distance. Wrigley field is close. The price is a value in the winter months but goes up during the vacation seasons. "

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

"Room was very nice, clean. The staff was helpful and the location was near public transportation to downtown Chicago "

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

"Great location, very nice staff, fun decor, large guest room at a great price!"

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

"Great location. Clean room. Pleasant staff"

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

## Find out more about North Side

## North Side Vacation Homes information

| Number of reviews | 366               |
| ----------------- | ----------------- |
| Accommodation     | 76 Vacation Homes |
| Lowest Price      | CA $219           |
| Highest Price     | CA $1,179         |

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