Title: North Side Vacation Home Rentals from CA $244: 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

[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)

In two months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-07-03&endDate=2026-07-05&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

![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)

6.0/10

(2 reviews)

"We were very disappointed with our stay. The property did not match the listing in several important ways. There were not enough beds for our group as advertised, and we were informed about basement flooding just one day before arrival — despite being told on-site that it had occurred months earlier. That lack of transparency was concerning. We also experienced confusion around check-in timing and had difficulty accessing the building. Overall, for the price paid, the experience did not meet...

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

Michael N.

CA $789

CA $2,680 total

includes taxes & fees

Apr 13 - Apr 14

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

![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/d1a40a0c.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)

### 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

(34 reviews)

"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"

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

Fred D.

CA $131

CA $333 total

includes taxes & fees

Mar 18 - Mar 19

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

![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)

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

![Smart TV, books](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/f698e846.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)

9.6/10

Exceptional

(22 reviews)

"I had a fun stay "

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

Jusu K.

CA $170

CA $244 total

includes taxes & fees

Mar 18 - Mar 19

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

![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/932d3e6c.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)

![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)

### Vacation Home in Worth

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

9.4/10

Exceptional

(57 reviews)

"Home was exactly what we were needing fir our stay. Host was responsive and timely. "

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

Stephanie H.

CA $211

CA $459 total

includes taxes & fees

Mar 15 - Mar 16

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

![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)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/079e5c97.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

(78 reviews)

"Nice , private and peaceful definitely will be back "

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

BRANDEN J.

CA $134

CA $268 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.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/d36efedf.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)

### 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)

"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"

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

JOSE S.

CA $202

CA $415 total

includes taxes & fees

Mar 23 - Mar 24

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

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x59y0-8cb3eda8.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

(20 reviews)

"Great place Great location "

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

Josh W.

CA $232

CA $592 total

includes taxes & fees

Mar 17 - Mar 18

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

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/699d0fa8.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)

![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)

### Vacation Home in Oak Park

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

10/10

Exceptional

(14 reviews)

"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."

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

Beryl I.

CA $233

CA $698 total

includes taxes & fees

Mar 18 - Mar 19

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

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

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/0900c857.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)

![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)

### Vacation Home in Oak Park

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

10/10

Exceptional

(29 reviews)

"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "

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

Lawrence P.

CA $234

CA $698 total

includes taxes & fees

Mar 17 - Mar 18

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

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/839ff6dd.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)

![Interior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/524cef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Elmhurst

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

10/10

Exceptional

(16 reviews)

"Clean rooms, very helpful and friendly host, the house had everything we needed"

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

Kaitlyn M.

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

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/d3b24fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/39dd5566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/dad32a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/90a99332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oakton

[](https://www.expedia.ca/Chicago-Hotels-Your-Next-Vacation-Home.h96685294.Hotel-Information)

9.4/10

Exceptional

(67 reviews)

"We enjoyed our stay"

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

Lukose K.

CA $233

CA $451 total

includes taxes & fees

Mar 18 - Mar 19

[](https://www.expedia.ca/Chicago-Hotels-Your-Next-Vacation-Home.h96685294.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)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d0b74272.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)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d30bfd55.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 $322

CA $553 total

includes taxes & fees

Apr 13 - Apr 14

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

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/1a2e5255.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)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/0dd7d579.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)

### Vacation Home in Burbank

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

8.6/10

Excellent

(7 reviews)

"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 $262

CA $645 total

includes taxes & fees

Apr 5 - Apr 6

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

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/27ecf0e1.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)

![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)

### Vacation Home in Elmhurst

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

8.8/10

Excellent

(40 reviews)

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

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

Terrence M.

CA $135

CA $372 total

includes taxes & fees

Mar 25 - Mar 26

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

![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)

![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1433h1080x93y0-253226e3.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)

### Vacation Home in South Shore

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

CA $125

CA $744 total

includes taxes & fees

Mar 24 - Mar 25

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

![Living area](https://images.trvl-media.com/lodging/126000000/125770000/125767500/125767485/eb982d34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125770000/125767500/125767485/8d281ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125770000/125767500/125767485/efecf791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/126000000/125770000/125767500/125767485/91f02bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westmont

[](https://www.expedia.ca/Chicago-Hotels-Suoer-Sleek-Large-Tiny-House-By-Westmont-Metra.h125767485.Hotel-Information)

CA $147

CA $267 total

includes taxes & fees

Mar 18 - Mar 19

[](https://www.expedia.ca/Chicago-Hotels-Suoer-Sleek-Large-Tiny-House-By-Westmont-Metra.h125767485.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/126000000/125590000/125580900/125580870/ab001f67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125590000/125580900/125580870/45a98814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/126000000/125590000/125580900/125580870/0bbde252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125590000/125580900/125580870/1e4f301a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Brookfield

[](https://www.expedia.ca/Chicago-Hotels-Spacious-2BR-Retreat-Full-Basement-Coffee-Bar-Pet-Friendly.h125580870.Hotel-Information)

CA $188

CA $522 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Chicago-Hotels-Spacious-2BR-Retreat-Full-Basement-Coffee-Bar-Pet-Friendly.h125580870.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w507h683x260y0-447e4031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w536h683x248y0-2cd4d36f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w508h683x259y0-9b6c1832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w507h683x259y0-fd391321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Des Plaines

[](https://www.expedia.ca/Houston-Hotels-Cozy-Home-By-OHare-EV-Plug.h118756057.Hotel-Information)

9.6/10

Exceptional

(7 reviews)

"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."

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

Michael H.

CA $223

CA $471 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Houston-Hotels-Cozy-Home-By-OHare-EV-Plug.h118756057.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)

![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)

![Interior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/4834f018.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

(35 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 $453

CA $970 total

includes taxes & fees

Mar 30 - Mar 31

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

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## 

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cottages

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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=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=VACATION_HOME)

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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

"I only spent one night at this hotel due to a travel delay so my experience was somewhat limited, however I felt very welcomed. The bed was comfortable, the staff was pleasant and the common area was quite charming. The location is ideal and close to public transportation. I would definitely book a future stay at this hotel. "

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

![The Willows Hotel](https://images.trvl-media.com/lodging/1000000/10000/7400/7374/7282b2ef_y.jpg)

### The Willows Hotel

8/10 Good

"The only issue was that they do not make up the room or change the towels unless you request it each day. Also, they provided only two sets of towels per room but my wife likes a second towel for her hair. You can get an extra towel but you have to request it each day. Other than that, it has a great location. The staff was friendly and it was clean. It is an older building."

[](https://expedia.ca/Chicago-Hotels-The-Willows-Hotel.h7374.Hotel-Information)

![The Hotel at Midtown](https://images.trvl-media.com/lodging/19000000/18390000/18385300/18385274/92b6393d_y.jpg)

### The Hotel at Midtown

10/10 Excellent

"Had a great time spending the night here with my Fiance. It is an athletic club so there is a great two story fitness center / weight room. Indoor tennis courts and swimming lanes. There is a attached secure parking garage to make your trip even easier. Overall, we had no issues with our stay. "

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

![The Neighborhood Hotel - Lincoln Park](https://images.trvl-media.com/lodging/87000000/86510000/86506600/86506502/31e9fa5d_y.jpg)

### The Neighborhood Hotel - Lincoln Park

8/10 Good

"Very clean and welcoming. Did not have any need to interact with staff other than a quick text when leaving. Only caveat: We were on the fourth floor and there is no elevator, so arriving and even departing were a little challeging with luggage. "

[](https://expedia.ca/Chicago-Hotels-The-Neighborhood-Hotel-Lincoln-Park.h86506502.Hotel-Information)

![Hotel Versey Chicago Lincoln Park](https://images.trvl-media.com/lodging/1000000/30000/23000/22993/ea5be619_y.jpg)

### Hotel Versey Chicago Lincoln Park

10/10 Excellent

"I was only able to stay one night in Hotel Versey and wish I could have stayed longer. The lobby's decoration is artistic and gorgeous. The clean smell hits you as soon as you walk through the doors. The staff was very helpful and friendly. The rooms are clean and the beds are some of the most comfortable I've ever slept in. I live in Lincoln Park, so I won't need to stay there often, but I will certainly have friends and family who visit stay at Hotel Versey!"

[](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/1000000/120000/116900/116850/5999266e_y.jpg)

### Best Western Plus Hawthorne Terrace Hotel

6/10 Okay

"Parking is expensive if you need an EV charger."

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

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

### Hotel Lincoln

8/10 Good

"Staff"

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

![The Chicago Hotel Collection - Wrigleyville](https://images.trvl-media.com/lodging/24000000/23610000/23604900/23604891/441ad9d1_y.jpg)

### The Chicago Hotel Collection - Wrigleyville

4/10 Poor

"The room is infested with mites that cause scabies"

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

![Hotel Zachary Chicago, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/24000000/23060000/23056000/23055991/2a337a36_y.jpg)

### Hotel Zachary Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"We enjoyed everything about Hotel Zachary - the location right across the street from Wrigley Field, the neighborhood, the room, the staff, the 2nd floor bar and gathering space, the bagel shop on the first floor. "

[](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 | 450               |
| ----------------- | ----------------- |
| Accommodation     | 76 Vacation Homes |
| Lowest Price      | CA $244           |
| Highest Price     | CA $2,680         |

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- [Visit Bucktown ](https://www.expedia.ca/Chicago-Bucktown.dx553248622905536905)
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- [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)

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