Title: Northwest Side Vacation Rentals from CA $176: Short-Term Rentals for 2026 | Expedia.ca

[Northwest Side Travel Guide](https://expedia.ca/Northwest-Side.dx553248635976475367)[Hotels in Northwest Side](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[Flights to Northwest Side](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[Northwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[Northwest Side Vacation Packages](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides)

![Bloomingdale Trail, The 606, is an elevated pedestrian trail that travels through the Bucktown and Humboldt Park neighborhoods on Chicago's northwest side. Streets of Chicago.](https://images.trvl-media.com/place/553248635976475367/bfa3a438-7753-4d4b-b110-6e23898993ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248635976475367/bfa3a438-7753-4d4b-b110-6e23898993ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&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 four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&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)

## Our top choices for Northwest Side vacation rentals

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/2c7aa314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/0a306ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/f36c801f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/12a5de83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 2BR Haven Near Irving Park

[](https://www.expedia.ca/Chicago-Hotels-Chic-2BR-Haven-Near-Irving-Park.h116793191.Hotel-Information)

Irving Park

9.8/10

Exceptional

(9 reviews)

"Ample accommodations for two adults. Clean and in great condition!"

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

Kathy D.

CA $94

CA $261 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Chic-2BR-Haven-Near-Irving-Park.h116793191.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/691b4cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/5f81cc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/0c96778e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/5f8949d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homey 2BR Apt w/ Parking

[](https://www.expedia.ca/Chicago-Hotels-Homey-2BR-Apt-W-Parking.h116792819.Hotel-Information)

Portage Park

9.4/10

Exceptional

(9 reviews)

"The location was ideal for us and had a grocery store, a Starbucks and CVS close by . The neighborhood was safe for walking around . Beds comfortable and whole place was very clean . I would stay here again . "

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

Sharlene T.

CA $94

CA $261 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Chicago-Hotels-Homey-2BR-Apt-W-Parking.h116792819.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/bc53e5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/253117f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/a5376f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/f308661a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Sunlit 1BR Apartment

[](https://www.expedia.ca/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information)

Irving Park

9.2/10

Wonderful

(12 reviews)

"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."

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

Brandon M.

CA $86

CA $229 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792686/3fdf6b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792686/08099623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792686/77d4b064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792686/1645c3e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Chic & Comfortable Furnished Unit

[](https://www.expedia.ca/Chicago-Hotels-2BR-Chic-Comfortable-Furnished-Unit.h116792686.Hotel-Information)

Hermosa

10/10

Exceptional

(4 reviews)

"Comfortable beds, great location"

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

Jason

CA $94

CA $261 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-2BR-Chic-Comfortable-Furnished-Unit.h116792686.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793177/1958fbd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793177/6bc6118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793177/809be077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793177/d2b3bef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Cozy & Functional Unit

[](https://www.expedia.ca/Chicago-Hotels-Harmonious-2BR-Apartment.h116793177.Hotel-Information)

Belmont Cragin

10/10

Exceptional

(1 review)

"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"

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

Laura V.

CA $94

CA $261 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Harmonious-2BR-Apartment.h116793177.Hotel-Information)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792749/04febcdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792749/e066e291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792749/4739f438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792749/64e861b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright Spaced 3BR Furnished Stay

[](https://www.expedia.ca/Chicago-Hotels-Bright-Spaced-3BR-Furnished-Stay.h116792749.Hotel-Information)

Portage Park

9.4/10

Exceptional

(3 reviews)

"Quick communication, great value, clean & bright."

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

Barb S.

CA $120

CA $319 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Bright-Spaced-3BR-Furnished-Stay.h116792749.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/613980fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/bb63d017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/e0a42d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/9655a9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trendy & Comfy Studio Unit

[](https://www.expedia.ca/Chicago-Hotels-Trendy-Comfy-Studio-Unit.h116792702.Hotel-Information)

Portage Park

9.6/10

Exceptional

(5 reviews)

"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "

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

Courtney V.

CA $82

CA $211 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Chicago-Hotels-Trendy-Comfy-Studio-Unit.h116792702.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/1d9ed1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/332b86b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/b2ab5672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/5424523b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 2BR with Parking Near United Center & Wrigley

[](https://www.expedia.ca/Chicago-Hotels-2BR-Airy-Apt-W-Free-Parking.h116792822.Hotel-Information)

Portage Park

9.2/10

Wonderful

(5 reviews)

"Cleanliness. Roomy. Comfortable mattresses. Fluffy, white bath towels. Ample towel racks in bathrooms. Attentive hostess. Off street parking greatly appreciated but garage door opener should be operative."

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

MARGARET L.

CA $94

CA $268 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Chicago-Hotels-2BR-Airy-Apt-W-Free-Parking.h116792822.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/61a49b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/025f2d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/46b687b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/722215ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pine Beam Sloth Apartment next to Blue Line

[](https://www.expedia.ca/Chicago-Hotels-Boho-1-Bedroom-Pine-Beam-Condo-Next-To-Blue-Line.h108439787.Hotel-Information)

Irving Park

10/10

Exceptional

(5 reviews)

"Beautifully decorated, spotless unit. Conveniently located."

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

Holly G.

CA $154

CA $336 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Boho-1-Bedroom-Pine-Beam-Condo-Next-To-Blue-Line.h108439787.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/32fa6eee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/e98b2c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/ee4eaca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/aeb10a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright, Clean, and Furnished Studio Unit

[](https://www.expedia.ca/Chicago-Hotels-Comfy-Studio-In-Portage-Park-Great-Value.h116792785.Hotel-Information)

Portage Park

10/10

Exceptional

(1 review)

"The host was very friendly, helpful, and communicative. The apartment was clean and quiet. "

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

Clifton C.

CA $82

CA $211 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Comfy-Studio-In-Portage-Park-Great-Value.h116792785.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/8792a35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/4cd31799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/d39f043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/21edda64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Studio in Portage Park

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Studio-In-Portage-Park.h116792792.Hotel-Information)

Portage Park

CA $94

CA $225 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Studio-In-Portage-Park.h116792792.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/c6227841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/7f2b0ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/f1329ccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/ff1deed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2BR Apt for a Seamless Stay

[](https://www.expedia.ca/Chicago-Hotels-Cozy-2BR-Apt-For-A-Seamless-Stay.h116792645.Hotel-Information)

Portage Park

8.0/10

Very good

(1 review)

"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "

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

Michael P.

CA $94

CA $261 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Chicago-Hotels-Cozy-2BR-Apt-For-A-Seamless-Stay.h116792645.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792434/843ed2e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792434/05d4ef1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792434/90c76e46.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/117000000/116800000/116792500/116792434/a3844b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1-Bedroom Apartment

[](https://www.expedia.ca/Chicago-Hotels-Cozy-1-Bedroom-Apartment-Sunnyside-2N.h116792434.Hotel-Information)

Portage Park

10/10

Exceptional

(1 review)

"The place was great! It's stocked with the basics, bed and couch are comfy, and everything is clean. There were only a handful of times when I heard the upstairs neighbor, but nothing too crazy. The neighborhood itself is very cute and quiet, with good food and stores within walking distance. Street parking was easy. Thank you! "

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

Sarah M.

CA $89

CA $233 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Cozy-1-Bedroom-Apartment-Sunnyside-2N.h116792434.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/e3c3ee61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/976894c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/e9a50a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/3bd0ca23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Apartment with a Warm & Welcoming Feel

[](https://www.expedia.ca/Chicago-Hotels-1BR-Homey-Apt-In-Irving-Park.h116792651.Hotel-Information)

Irving Park

9.0/10

Wonderful

(4 reviews)

"It was wonderful and wil stay agian"

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

Crystal P.

CA $86

CA $229 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Chicago-Hotels-1BR-Homey-Apt-In-Irving-Park.h116792651.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792981/0ae224ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792981/2c87bc26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792981/3cf6e1d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792981/bc28dbf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Portage Park 1BR Retreat

[](https://www.expedia.ca/Chicago-Hotels-Portage-Park-1BR-Retreat.h116792981.Hotel-Information)

Portage Park

8.8/10

Excellent

(3 reviews)

"Clean comfortable space, friendly host, location was very convenient for our needs, with a short walk to the CTA. The only drawbacks were minor; there are no curtains-only blinds- which let in more morning light than we would have liked for sleeping in and there was minimal space in the bathroom for counter items and hanging up towels, travel kits ext."

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

Brienne K.

CA $86

CA $229 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Portage-Park-1BR-Retreat.h116792981.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793168/bd507604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793168/9f14f876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793168/a28c0942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793168/00100f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ideal & Spacious 1BR Apt

[](https://www.expedia.ca/Chicago-Hotels-Ideal-Spacious-1BR-Apt.h116793168.Hotel-Information)

Irving Park

8.0/10

Very good

(2 reviews)

"Excellent location. Clean. Quiet building. Host was incredibly responsive. There was a blizzard during our stay and the host graciously accomodated our request to extend our visit!"

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

Jackie F.

CA $86

CA $229 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Ideal-Spacious-1BR-Apt.h116793168.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811946/8dfa98f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811946/1ba32704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811946/6a454586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811946/91128bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 4 • New Modern 1BR • Private Workspace

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-4-New-Modern-1BR-Private-Workspace.h122811946.Hotel-Information)

Irving Park

CA $71

CA $371 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-4-New-Modern-1BR-Private-Workspace.h122811946.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811823/7d5e3da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811823/5a7cdc92.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/123000000/122820000/122811900/122811823/0abfad39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811823/b2746b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Fitness Pad • Private Gym • Sleeps 7

[](https://www.expedia.ca/Chicago-Hotels-2BR-Fitness-Pad-Private-Gym-Sleeps-7.h122811823.Hotel-Information)

Irving Park

CA $82

CA $385 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-2BR-Fitness-Pad-Private-Gym-Sleeps-7.h122811823.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811874/795dd9d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811874/b59677e7.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/123000000/122820000/122811900/122811874/97fb1955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811874/401af137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR w/ Workspace - Coffee Bar - Near Transit

[](https://www.expedia.ca/Chicago-Hotels-2BR-W-Workspace-Coffee-Bar-Near-Transit.h122811874.Hotel-Information)

Belmont Cragin

CA $72

CA $484 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-2BR-W-Workspace-Coffee-Bar-Near-Transit.h122811874.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122730000/122720500/122720494/d08b2a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122730000/122720500/122720494/5ebc6f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122730000/122720500/122720494/30a145dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122730000/122720500/122720494/0e6b1f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Clean and Serene Apartment

[](https://www.expedia.ca/Chicago-Hotels-1BR-Clean-And-Serene-Apartment.h122720494.Hotel-Information)

Belmont Cragin

CA $86

CA $229 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-1BR-Clean-And-Serene-Apartment.h122720494.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-01&endDate=2026-03-02&regionId=553248635976475367&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VACATION_HOME)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=RESIDENCE)

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## Top Northwest Side Hotel Reviews

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Yes"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"It was great "

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Service, history, "

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Great staff, awesome location, and clean rooms"

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Great stay "

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Great location, beautiful historic hotel with clean, updated rooms. "

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

" Friendly staff, tasteful room"

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg)

### DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"The hotel was a 10 out of 10.. and the cookies were so good"

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Great service "

[](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

## Find out more about Northwest 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 Northwest 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.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Northwest Side

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- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Apartments in Northwest Side ](https://expedia.ca/Northwest-Side-Apartments.d553248635976475367-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Northwest Side ](https://expedia.ca/Northwest-Side-Private-Vacation-Homes.d553248635976475367-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Northwest Side ](https://expedia.ca/Northwest-Side-Condos.d553248635976475367-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Northwest Side ](https://expedia.ca/Northwest-Side-Apart-Hotels.d553248635976475367-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Northwest Side ](https://expedia.ca/Northwest-Side-Motels.d553248635976475367-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Northwest Side ](https://expedia.ca/Northwest-Side-Cottages.d553248635976475367-aaCottages.Travel-Guide-Accommodation)
- [B&B in Northwest Side ](https://expedia.ca/Northwest-Side-Bed-And-Breakfast.d553248635976475367-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Northwest Side ](https://expedia.ca/Northwest-Side-Guest-Houses.d553248635976475367-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Northwest Side ](https://expedia.ca/Northwest-Side-Hostels.d553248635976475367-aaHostels.Travel-Guide-Accommodation)
- [Resorts in Northwest Side ](https://expedia.ca/Northwest-Side-Resort-Hotels.d553248635976475367-aaResortHotels.Travel-Guide-Accommodation)
- [Villas in Northwest Side ](https://expedia.ca/Northwest-Side-Villas.d553248635976475367-aaVillas.Travel-Guide-Accommodation)
- [Farmstay in Northwest Side ](https://expedia.ca/Northwest-Side-Agritourism.d553248635976475367-aaAgritourism.Travel-Guide-Accommodation)

### Expedia's Latest Trends

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Cars

- [Enterprise Car Rentals In West Side](https://expedia.ca/Enterprise-Car-Rentals-In-West-Side.d553248635976475400-c15.Car-Rental-Guide-Suppliers)
- [Dollar Rent A Car Car Rentals In Central Chicago](https://expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Central-Chicago.d553248635976475413-c43.Car-Rental-Guide-Suppliers)

Packages

- [Art Institute of Chicago](https://expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
- [United Center](https://expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
- [Navy Pier](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)
- [Lincoln Park Zoo](https://expedia.ca/Lincoln-Park-Zoo-Lincoln-Park.d6065147.Vacation-Attraction)
- [Chicago Riverwalk](https://expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction)
- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Robie House](https://expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)
- [875 North Michigan Avenue](https://expedia.ca/875-North-Michigan-Avenue-Downtown-Chicago.d6065131.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Millennium Park](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Water Tower Place](https://expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)
- [Wrigley Field](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

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