Title: North Side Vacation Rentals from CA $162: 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

In two weeks

[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)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475406&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three 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 four 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)

## Our top choices for North Side vacation rentals

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/c25a1316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/5dcfd7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/2626f596.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)

"Excellent location and very clean! Would stay again!"

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

Jacob

CA $138

CA $162 total

includes taxes & fees

Dec 29 - Dec 30

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

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/cd395b25.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)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/c5808a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/322fd87f.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

(54)

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

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

Carin O.

CA $183

CA $452 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

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

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792938/93d35657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792938/dad4fcd7.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 $100

CA $267 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/9992e92b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/f623e866.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)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/26ab6432.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 $100

CA $267 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120647300/120647237/9937671c.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)

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

![Interior](https://images.trvl-media.com/lodging/121000000/120650000/120647300/120647237/f475fabc.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)

9.0/10

Wonderful

(4)

"Excellent location. Easy walkability to Whole Foods and restaurants. Shubas just down the road. A little confusion on checking in but all worked out great."

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

David G.

CA $82

CA $226 total

includes taxes & fees

Dec 30 - Dec 31

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

![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)

![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/117000000/116800000/116793200/116793125/32383df5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793125/5b9dd3bc.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

(30)

"Awesome place to stay. "

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

Gary

CA $101

CA $340 total

includes taxes & fees

Dec 30 - Dec 31

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/0d2a45ce.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)

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/76b820e4.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 $262 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/e37c62cd.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)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/c434b940.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)

9.0/10

Wonderful

(38)

"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 $265 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/93b6d18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/51c581a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/2740956d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/w1007h1024x0y0-beaf9548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Prime-Location-2BR-Near-Wrigley.h116792848.Hotel-Information)

9.6/10

Exceptional

(7)

"We chose this location bsed on the proximity to Wrigley Field. It was very convenient and the place fit our needs! "

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

Erica B.

CA $86

CA $251 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chicago-Hotels-Prime-Location-2BR-Near-Wrigley.h116792848.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793187/58e7cdce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793187/dce3b0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793187/e5d11d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793187/96ea18a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North Center

[](https://www.expedia.ca/Chicago-Hotels-Bright-Comfortable-1-Bedroom-Unit.h116793187.Hotel-Information)

CA $86

CA $230 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-Bright-Comfortable-1-Bedroom-Unit.h116793187.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)

9.4/10

Exceptional

(9)

"What an amazing location! Unbeatable! Great walking access to dining and entertainment. Great way to experience Chicago!"

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

Tom S.

CA $103

CA $294 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792798/9adb6e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792798/039a83db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792798/35052b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792798/700f488d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Lovely-1BR-Apt-In-Lakeview.h116792798.Hotel-Information)

9.0/10

Wonderful

(6)

"Great apartment, great location, and excellent host."

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

Benjamin N.

CA $88

CA $232 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](https://www.expedia.ca/Chicago-Hotels-Lovely-1BR-Apt-In-Lakeview.h116792798.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793130/a0beb4d8.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)

![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)

### 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 $82

CA $212 total

includes taxes & fees

Dec 29 - Dec 30

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

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793038/165fb9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793038/f1d5e216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793038/efe23946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793038/c81168a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-1BR-Unit-W-2-Comfy-Beds.h116793038.Hotel-Information)

10/10

Exceptional

(2)

"Property was great. Stayed for 2 nights and you have everything you need within walking distance. Great communication and easy to navigate. "

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

Ethan S.

CA $88

CA $232 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-1BR-Unit-W-2-Comfy-Beds.h116793038.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793147/84717d11.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)

![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)

### 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 $82

CA $226 total

includes taxes & fees

Dec 29 - Dec 30

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

![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)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/71d6f8a3.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)

![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)

### Apartment in Lakeview

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

10/10

Exceptional

(13)

"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 1 - Jan 2, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/b7f43eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/d8c5cb46.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/114000000/113520000/113517100/113517065/ff8b4515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/148e02c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Spacious-Lakeview-Apartment-With-Games-Garage.h113517065.Hotel-Information)

8.0/10

Very good

(6)

"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"

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

Matthew B.

CA $108

CA $379 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Spacious-Lakeview-Apartment-With-Games-Garage.h113517065.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)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792869/f3e5e0d5.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 $112

CA $302 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/18ab8b81.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)

![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/117000000/116800000/116792900/116792861/255dfec9.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)

"Awesome "

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

Robert

CA $86

CA $230 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792908/a72bf2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792908/cebced9f.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/117000000/116800000/116793000/116792908/d96d9efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792908/fb28ac23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Smart-Stylish-2-Bedroom-Unit.h116792908.Hotel-Information)

9.4/10

Exceptional

(3)

"Good, walkable neighborhood. Nice room. "

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

Dawn N.

CA $96

CA $264 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-Smart-Stylish-2-Bedroom-Unit.h116792908.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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## 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

"Great room, FANTASTIC location and parking was a breeze! "

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

"Great location. Nice rooms. Beautiful lobby. Good breakfast. Pet friendly. "

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

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

### The Willows Hotel

10/10 Excellent

"A charming older hotel."

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

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

### Hotel Lincoln

10/10 Excellent

"Front desk and valet were excellent. Quick check in. "

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

![The Den Hotel](https://images.trvl-media.com/lodging/121000000/120770000/120768600/120768541/3bcbd431_y.jpg)

### The Den Hotel

10/10 Excellent

"Great location easy check in nice facilities "

[](https://expedia.ca/Chicago-Hotels-The-Den-Hotel.h120768541.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

"Nice hotel and rooms"

[](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

"The staff at the Hotel Zachary is amazing. Every person we met was friendly knowledgeable and helpful. The hotel was beautiful and super clean. The rooms are spacious and the views were phenomenal "

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

"Clean room. Great gym and convenient parking."

[](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

"Awesome location. P"

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

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