Title: North Side Vacation Rentals from CA $218: Short-Term Rentals for 2026 | 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)[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

# North Side Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-01-06&endDate=2026-01-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 7 - Jan 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-01-07&endDate=2026-01-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-01-16&endDate=2026-01-18&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 rentals

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e1fd538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3935f43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/7b407b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

9.6/10

Exceptional

(27)

"Nice place "

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

Barry

CA $205

CA $240 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/322fd87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/8a1e71e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/06df6711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/87e615f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North Center

[](https://www.expedia.ca/Chicago-Hotels-2-Bedroom-Apartment-Just-2-Minutes-Drive-To-Wrigley-Field.h105887915.Hotel-Information)

9.6/10

Exceptional

(56)

"Nice property, great location, super helpful host!"

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

Carin O.

CA $185

CA $456 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-2-Bedroom-Apartment-Just-2-Minutes-Drive-To-Wrigley-Field.h105887915.Hotel-Information)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/2146175e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/6f92a1cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/a067dc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/21d3545d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.Hotel-Information)

10/10

Exceptional

(45)

"Great spot in a wonderful location!"

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

Jasson R.

CA $198

CA $596 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120650000/120647300/120647237/04b9cc7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120650000/120647300/120647237/31dc42a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120650000/120647300/120647237/393db6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120647300/120647237/97c814c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-1BR-Fully-Equipped-Central.h120647237.Hotel-Information)

7.8/10

Good

(6)

CA $87

CA $232 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Chicago-Hotels-1BR-Fully-Equipped-Central.h120647237.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/bb00d0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/5d91d1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/ffd7b217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/efbabb04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Avondale

[](https://www.expedia.ca/Chicago-Hotels-1BR-Airy-Apartment-W-Wi-Fi.h116793158.Hotel-Information)

6.0/10

(2)

"The location of property was great.! Door to apt was a little complicated figuring out without key after entering code the first time .building is old you can tell with how the floors creek when you walk . Was a lot of damage inside the bathroom on Ceilings and wall like a bad water leak happened and a hole in bedroom like someone punched the wall next to the bed. The hot water did not seem to work well at all and took 20 mins just to heat up … it could use a touch up for sure and some tlc .....

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

Sierra H.

CA $95

CA $242 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-1BR-Airy-Apartment-W-Wi-Fi.h116793158.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793091/ca455a09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793091/5e4e9278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793091/605858c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793091/29cb9ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-Lakeview-Chicago.h116793091.Hotel-Information)

8.8/10

Excellent

(27)

"Terrific overall stay. Great location and nice place. Highly recommend."

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

Robin

CA $87

CA $232 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-Lakeview-Chicago.h116793091.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/08f44095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/68502f61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/0265aebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/2a679a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Avondale

[](https://www.expedia.ca/Chicago-Hotels-Chic-Fully-Furnished-2BR-Apt.h116792678.Hotel-Information)

10/10

Exceptional

(2)

"Our stay was great! The apartment is very clean and comfortable. Nicely furnished. On a residential street in a lovely neighborhood. Wifi and A/C units worked well (we were there in August). We found street parking pretty easily. And Kristine was a really responsive host. Would absolutely stay again!"

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

Stephanie D.

CA $101

CA $269 total

includes taxes & fees

Jan 8 - Jan 9

[](https://www.expedia.ca/Chicago-Hotels-Chic-Fully-Furnished-2BR-Apt.h116792678.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793125/5b9dd3bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793125/7fea6ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793125/94213371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793125/b59af6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lincoln Park

[](https://www.expedia.ca/Chicago-Hotels-Sleek-Style-3BR-Haven-Free-Parking.h116793125.Hotel-Information)

9.8/10

Exceptional

(31)

"Awesome place to stay. "

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

Gary

CA $109

CA $352 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Sleek-Style-3BR-Haven-Free-Parking.h116793125.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792938/5c6285c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792938/cbc0fd91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792938/318a08a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792938/44600189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Avondale

[](https://www.expedia.ca/Chicago-Hotels-Roscoe-Retreat-Cozy-2BR-In-Chicago.h116792938.Hotel-Information)

10/10

Exceptional

(1)

"The place was very nice, very clean and very comfortable beds. Location was great, it was a little cool in the evenings but we did visit during very cold weather. Would stay there again, especially in warmer weather. The host was great in answering questions right away. I hope they found us to have been good renters. "

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

Martha R.

CA $101

CA $269 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Roscoe-Retreat-Cozy-2BR-In-Chicago.h116792938.Hotel-Information)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/122000000/121440000/121433600/121433562/4ffacabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121440000/121433600/121433562/7ba3e3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121440000/121433600/121433562/13126a97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121440000/121433600/121433562/911eb175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-In-Excellent-Wrigleyville-Chicago.h121433562.Hotel-Information)

10/10

Exceptional

(2)

"Clean and location was amazing "

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

James H.

CA $187

CA $798 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-In-Excellent-Wrigleyville-Chicago.h121433562.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793300/116793218/a03ec2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793300/116793218/6f1deab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793300/116793218/bb9284f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793300/116793218/cd9fa0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North Center

[](https://www.expedia.ca/Chicago-Hotels-Cozy-3BR-Gem-In-North-Center.h116793218.Hotel-Information)

8.8/10

Excellent

(12)

"While the building and unit are older, the unit is very clean and the location is ideal. The bedding and towels were very nice, and there were plenty of pillows. Check in and out was very easy. "

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

Elise B.

CA $103

CA $293 total

includes taxes & fees

Jan 8 - Jan 9

[](https://www.expedia.ca/Chicago-Hotels-Cozy-3BR-Gem-In-North-Center.h116793218.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793130/4ee16877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793130/5ab3b5df.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/117000000/116800000/116793200/116793130/45b75917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793130/ef8372db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Lush-Studio-Apt-Summa.h116793130.Hotel-Information)

8.0/10

Very good

(4)

"Small cozy studio in a very quite building. Perfect for one person a couple. The host is very attentive and the place has everything you would need from towels to kitchen amenities. Definitely recommend!"

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

Gabriel M.

CA $87

CA $218 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Lush-Studio-Apt-Summa.h116793130.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792869/0b085046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792869/5ae5edbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792869/a4cf3783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792869/5f7cca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Avondale

[](https://www.expedia.ca/Chicago-Hotels-Comfy-3BR2BA-Logan-Square-Retreat.h116792869.Hotel-Information)

8.6/10

Excellent

(4)

"We stayed one night for a work trip. It was just what we needed. Host communication was frequent and helpful."

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

Jayme R.

CA $113

CA $304 total

includes taxes & fees

Jan 8 - Jan 9

[](https://www.expedia.ca/Chicago-Hotels-Comfy-3BR2BA-Logan-Square-Retreat.h116792869.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793147/cd5afd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793147/574db90e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793147/dd342ea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793147/a8cb286a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Vibrant-1BR-Apartment.h116793147.Hotel-Information)

9.4/10

Exceptional

(3)

"Easy check in/out. Good communication "

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

Sherri D.

CA $87

CA $232 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Chicago-Hotels-Vibrant-1BR-Apartment.h116793147.Hotel-Information)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793134/89663752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793134/80a58ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793134/0da84e57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793134/59261bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Avondale

[](https://www.expedia.ca/Chicago-Hotels-3BR-Apt-Prime-Spacious.h116793134.Hotel-Information)

6.0/10

(2)

"Very noisy air conditioner"

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

Ali

CA $113

CA $304 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-3BR-Apt-Prime-Spacious.h116793134.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792707/7f1a0b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792707/86ee05de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792707/3d108e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792707/980cff85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Fully-Set-Up-3BR-W-Big-Kitchen.h116792707.Hotel-Information)

9.0/10

Wonderful

(14)

"Great place. Great location. "

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

Adrianna S.

CA $109

CA $299 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Fully-Set-Up-3BR-W-Big-Kitchen.h116792707.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/80ce05ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/8b47b4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/2de3a410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/10d63c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Boystown-Chic-2BR-Escape.h116792813.Hotel-Information)

10/10

Exceptional

(14)

"Very clean and amazing comfortable stay!!"

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

Justin M.

CA $88

CA $254 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Boystown-Chic-2BR-Escape.h116792813.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/255dfec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/3bf54963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/bea75315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/7523a52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North Center

[](https://www.expedia.ca/Chicago-Hotels-1BR-Apartment-In-Chicago.h116792861.Hotel-Information)

8.8/10

Excellent

(15)

"Good location for us. Host was easy to communicate with"

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

Kayla K.

CA $87

CA $232 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-1BR-Apartment-In-Chicago.h116792861.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/35964ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/ad06b7cf.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/117000000/116800000/116792900/116792852/d94c7dbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/167366b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-2BR-Apt-Beautifully-Furnished.h116792852.Hotel-Information)

10/10

Exceptional

(9)

"We loved the place. The feeling of home away from home."

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

Sataish

CA $96

CA $264 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-2BR-Apt-Beautifully-Furnished.h116792852.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/b0debc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/0e0ab83d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/26d113a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/7d97851d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-In-Vibrant-Lakeview.h116792940.Hotel-Information)

9.2/10

Wonderful

(39)

"We have stayed at this property several times. It’s a great location. The apartment is cute and comfortable. "

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

Susie B.

CA $96

CA $264 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-In-Vibrant-Lakeview.h116792940.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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## Find vacation rentals that suit your style

Aparthotels

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Villas

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Condos

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Cottages

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Private vacation homes

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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=2026-04-06&d1=2026-04-06&endDate=2026-04-09&d2=2026-04-09&lodging=RESIDENCE)

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## 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

"Great"

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

"They should knock for food delivery."

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

"We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!"

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

![The Willows Hotel](https://images.trvl-media.com/lodging/1000000/10000/7400/7374/10ec6d68_y.jpg)

### The Willows Hotel

10/10 Excellent

"Clean room. Very cozy and quaint lobby area. The staff were very accommodating and friendly. It was in a perfect location, within walking distance to everything we needed. "

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

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

### The Majestic Hotel

10/10 Excellent

"Friendly staff and great location."

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

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

### Dorothy's

10/10 Excellent

"The room was small, but very comfortable. Initially, I was a bit leery of the "no reception; we'll send you a code" check-in, but it went very smoothly. The code worked on all the doors it was supposed to work on, and I appreciated the triple-layer of code security - outside door, door to the floor, door to the room. Dorothy's is ideally situated, and easy walking distance to attractions in the area, in addition to the Red line train and numerous bus lines. If I had to ding Dorothy's on anything, it's this: Coffeemate isn't cream and doesn't do the same in your coffee in the morning as does half-and-half. "

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

"Very clean room comfy bed great shower nice location "

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

![Wrigleyville Suites](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406_y.jpg)

### Wrigleyville Suites

10/10 Excellent

"Nice place "

[](https://expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

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

### City Suites Hotel

10/10 Excellent

"Our room was immaculate. "

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

## Find out more about North Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with North Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Apartments in North Side ](https://expedia.ca/North-Side-Apartments.d553248635976475406-aaApartments.Travel-Guide-Accommodation)
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- [Guest Houses in North Side ](https://expedia.ca/North-Side-Guest-Houses.d553248635976475406-aaGuestHouses.Travel-Guide-Accommodation)

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