Title: Holiday Rentals Northwest Side from £103: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Northwest Side Travel Guide](https://expedia.co.uk/Northwest-Side.dx553248635976475367)[Hotels in Northwest Side](https://expedia.co.uk/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[Flights to Northwest Side](https://expedia.co.uk/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[Northwest Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Northwest-Side.d553248635976475367.Car-Hire-Guide)[Northwest Side Holidays](https://expedia.co.uk/Northwest-Side.d553248635976475367.Holidays-City-Breaks) ![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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475367&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475367&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [15 May - 17 May](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475367&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [12 Jun - 14 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475367&startDate=2026-06-12&endDate=2026-06-14&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 holiday rentals ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/691b4cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/1873d217.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) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/5f81cc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homey 2BR Apt w/ Parking [](https://www.expedia.co.uk/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. £144 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Homey-2BR-Apt-W-Parking.h116792819.Hotel-Information) ![1 bedroom, iron/ironing board, travel cot, 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) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/f308661a.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) ### Charming Sunlit 1BR Apartment [](https://www.expedia.co.uk/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. £128 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information) ![Iron/ironing board, travel cot, 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/117000000/116800000/116792800/116792702/9655a9e1.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/117000000/116800000/116792800/116792702/8ceff1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trendy & Comfy Studio Unit [](https://www.expedia.co.uk/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. £118 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Trendy-Comfy-Studio-Unit.h116792702.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/2c7aa314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/aadb2c31.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) ![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) ### Chic 2BR Haven Near Irving Park [](https://www.expedia.co.uk/Chicago-Hotels-Chic-2BR-Haven-Near-Irving-Park.h116793191.Hotel-Information) Irving Park 9.8/10 Exceptional (10 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. £144 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Chic-2BR-Haven-Near-Irving-Park.h116793191.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) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/daec8fd7.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) ### Lovely 2BR with Parking Near United Center & Wrigley [](https://www.expedia.co.uk/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. £148 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-2BR-Airy-Apt-W-Free-Parking.h116792822.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) ![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) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792686/941e594f.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) ### 2BR Chic & Comfortable Furnished Unit [](https://www.expedia.co.uk/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 £144 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-2BR-Chic-Comfortable-Furnished-Unit.h116792686.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) ![Shower](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792749/64e861b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792749/36f7deb8.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) ### Bright Spaced 3BR Furnished Stay [](https://www.expedia.co.uk/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. £174 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Bright-Spaced-3BR-Furnished-Stay.h116792749.Hotel-Information) ![Smart TV, stereo](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/5a5bc081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/532e4902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/16704f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/0c278201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Beam Sloth Apartment next to Blue Line [](https://www.expedia.co.uk/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. £184 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Boho-1-Bedroom-Pine-Beam-Condo-Next-To-Blue-Line.h108439787.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) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/5a357341.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) ### Cozy 2BR Apt for a Seamless Stay [](https://www.expedia.co.uk/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. £144 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-2BR-Apt-For-A-Seamless-Stay.h116792645.Hotel-Information) ![Iron/ironing board, travel cot, 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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/ee4eaca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/edf7b63c.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.co.uk/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. £118 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Comfy-Studio-In-Portage-Park-Great-Value.h116792785.Hotel-Information) ![Iron/ironing board, travel cot, 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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/7d4b0fa0.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) ### Cozy Studio in Portage Park [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Portage-Park.h116792792.Hotel-Information) Portage Park £126 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Portage-Park.h116792792.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/e9a50a42.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) ![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.co.uk/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. £128 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-1BR-Homey-Apt-In-Irving-Park.h116792651.Hotel-Information) ![2 bedrooms, iron/ironing board, travel cot, 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.co.uk/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. £144 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Harmonious-2BR-Apartment.h116793177.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) ![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811946/6a454586.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811946/37711f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleeps 4 • New Modern 1BR • Private Workspace [](https://www.expedia.co.uk/Chicago-Hotels-Sleeps-4-New-Modern-1BR-Private-Workspace.h122811946.Hotel-Information) Irving Park £202 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Sleeps-4-New-Modern-1BR-Private-Workspace.h122811946.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/3766e1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/6b4d943a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/147b4824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/3ea06204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2BR Apartment w/ Washer & Dryer [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-2BR-Apt-W-Washer-Dryer.h116792669.Hotel-Information) Portage Park £144 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-2BR-Apt-W-Washer-Dryer.h116792669.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/123000000/122820000/122811900/122811823/936e2c5b.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) ![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.co.uk/Chicago-Hotels-2BR-Fitness-Pad-Private-Gym-Sleeps-7.h122811823.Hotel-Information) Irving Park £210 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-2BR-Fitness-Pad-Private-Gym-Sleeps-7.h122811823.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811871/62fbd145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811871/35a81e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811871/2da170da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122820000/122811900/122811871/0a131ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR • Sleeps7 • Coffee Station • Backyard w/ Grill [](https://www.expedia.co.uk/Chicago-Hotels-2BR-Sleeps7-Coffee-Station-Backyard-W-Grill.h122811871.Hotel-Information) Belmont Cragin £263 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-2BR-Sleeps7-Coffee-Station-Backyard-W-Grill.h122811871.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) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792981/a65d77aa.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) ### Portage Park 1BR Retreat [](https://www.expedia.co.uk/Chicago-Hotels-Portage-Park-1BR-Retreat.h116792981.Hotel-Information) Portage Park 8.8/10 Excellent (3 reviews) "Great stay. Very good instructions along with video for entry. Clean and comfortable! Enjoyed our stay. Great Colombian coffee shop right downstairs to the right of the entrance." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann F. £128 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/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) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793168/00100f40.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) ### Ideal & Spacious 1BR Apt [](https://www.expedia.co.uk/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. £128 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Ideal-Spacious-1BR-Apt.h116793168.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) ![Iron/ironing board, travel cot, 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) ![TV, offices](https://images.trvl-media.com/lodging/123000000/122730000/122720500/122720494/dedd19be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Clean and Serene Apartment [](https://www.expedia.co.uk/Chicago-Hotels-1BR-Clean-And-Serene-Apartment.h122720494.Hotel-Information) Belmont Cragin £128 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-03-07&endDate=2026-03-08®ionId=553248635976475367&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_SPRING_PROMO_553248635976475367) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APARTMENT) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=VILLA) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=CONDO) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=COTTAGE) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Northwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475367&latLong=41.942624%2C-87.765702&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FNorthwest-Side-Holiday-Rentals.d553248635976475367.Travel-Guide-HolidayRentals)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNorthwest-Side-Holiday-Rentals.d553248635976475367.Travel-Guide-HolidayRentals) ## Top Northwest Side Hotel Reviews ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Great location. Rooms were clean no comfortable beds. " [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "Everything was great" [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mart-Plaza.h5467.Hotel-Information) ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg) ### Fairmont Chicago at Millennium Park 10/10 Excellent "Everything was great. From check-in to the room. Will definitely stay here again. 10/10" [](https://expedia.co.uk/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Beautiful place" [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.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 "Clean room, friendly staff " [](https://expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Very good " [](https://expedia.co.uk/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.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 "Classic older and well maintained hotel. " [](https://expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.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 "Staff was pleasant, breakfast was good and was sooo covenient to not have to worry about. My room was very tidy, the location was great, i walked to all of the places i wanted to go, in under 15mins. I am looking forwards to seeing chicago in the summer months and i would stay here again. " [](https://expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![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 "The room was very nice and spacious! I traveled with my family, so it was 4 of us in which it was perfect, nice views as well! Great front desk." [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ## Find out more about Northwest Side **Everything you need to know about** **Northwest Side** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Northwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Northwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Northwest Side holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Northwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Northwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Northwest Side holiday rentals we have selected for you start as low as £103 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Northwest Side rentals** At Expedia, we put the best Northwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Northwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Northwest Side holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Northwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk - All accommodation types in Northwest Side ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold ](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District ](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals ](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - 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[House of Blues Chicago hotels](https://expedia.co.uk/House-Of-Blues-Chicago-Hotels.0-l6227753-0.Travel-Guide-Filter-Hotels) - [Moonlight Hotel](https://expedia.co.uk/Hersonissos-Hotels-Moonlight-Hotel.h19477661.Hotel-Information) - [United Center hotels](https://expedia.co.uk/United-Center-Hotels.0-l6064077-0.Travel-Guide-Filter-Hotels) - [Navy Pier hotels](https://expedia.co.uk/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels) - [Michigan Avenue hotels](https://expedia.co.uk/Michigan-Avenue-Hotels.0-l6156167-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Pearl-Qatar](https://expedia.co.uk/5Star-The-Pearl-Qatar-Hotels.s50-0-d6361053.Travel-Guide-Filter-Hotels) - [Milton Keynes Accommodation](https://expedia.co.uk/Milton-Keynes-Hotels.d8370.Travel-Guide-Hotels) - [McCormick Place hotels](https://expedia.co.uk/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels) - [Hotels in De Pijp](https://expedia.co.uk/De-Pijp-Amsterdam-Hotels.0-n6052212-0.Travel-Guide-Filter-Hotels) - [All-Inclusive Hotels in Colombia](https://expedia.co.uk/Destinations-In-Colombia-All-Inclusive-Hotel.0-0-d38-tAllInclusiveHotel.Hotel-Filter-Destinations) Flights - [GLA to TYO flights](https://expedia.co.uk/lp/flights/gla/tyo/glasgow-to-tokyo) - [Flights to TRN](https://expedia.co.uk/Cheap-Flights-To-Turin-Intl.d5132884.Travel-Guide-Flights) Cars - [Car rental in Lake Meadows Park](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) Activities - [Things to do in Central Chicago](https://expedia.co.uk/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities) - [Things to do in Vancouver](https://expedia.co.uk/Things-To-Do-In-Vancouver.d178315.Travel-Guide-Activities) Packages - [Kingston Holidays](https://expedia.co.uk/Kingston.d180034.Holidays-City-Breaks) - [Chicago Theatre](https://expedia.co.uk/Chicago-Theatre-Downtown-Chicago.d6064049.Attraction) - [Grant Park](https://expedia.co.uk/Grant-Park-Downtown-Chicago.d507389.Attraction) - [Rother Valley Country Park](https://expedia.co.uk/Rother-Valley-Country-Park-Sheffield.d553248621532493026.Attraction) - [875 North Michigan Avenue](https://expedia.co.uk/875-North-Michigan-Avenue-Downtown-Chicago.d6065131.Attraction) - [Willis Tower](https://expedia.co.uk/Willis-Tower-Downtown-Chicago.d6064069.Attraction) - [Lincoln Park Zoo](https://expedia.co.uk/Lincoln-Park-Zoo-Lincoln-Park.d6065147.Attraction) - [Wrigley Field](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction) - [Art Institute of Chicago](https://expedia.co.uk/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Attraction) - [Millennium Park](https://expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction) - [Montrose Beach](https://expedia.co.uk/Montrose-Beach-Uptown.d6277595.Attraction) - [Navy Pier](https://expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction) - [Lincoln Park Conservatory](https://expedia.co.uk/Lincoln-Park-Conservatory-Lincoln-Park.d6065145.Attraction) General - [Visit Torremolinos](https://expedia.co.uk/Torremolinos.dx10205) - [Visit Laguna Beach](https://expedia.co.uk/Laguna-Beach.dx8384) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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