Title: Southwest Side Vacation Home Rentals from CA $407: Search Top Private Vacation Homes for Rent | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Southwest Side Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](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 [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southwest Side Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89290000/89289400/89289344/3704dbaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/90000000/89290000/89289400/89289344/b7a6661e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89290000/89289400/89289344/96b3585b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89290000/89289400/89289344/c97c92d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom. Glen Ellyn 10/10 Exceptional (25) "Great house, great neighborhood, host was amazing!" [](https://www.expedia.ca/Chicago-Hotels-4bd-House.h89289344.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/66000000/65360000/65358200/65358170/7fe3522c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65360000/65358200/65358170/346ee503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65360000/65358200/65358170/71a4db43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65360000/65358200/65358170/f9e8dfb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Belmont House, Classy & Chic/walk to Wrigley Field Lakeview 9.4/10 Exceptional (53) "Booked this place as we had a concert at Wrigley Field. The owner was phenomenal. 100% advertised. Great place to stay. 10 out of 10 would book again if in the area." [](https://www.expedia.ca/Chicago-Hotels-Belmont-House.h65358170.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68760000/68751700/68751679/w904h683x60y0-7856b4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68760000/68751700/68751679/2d76c5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/69000000/68760000/68751700/68751679/w1024h680x0y3-debcefb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68760000/68751700/68751679/w467h683x286y0-4b404cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony Downtown Chicago 9.2/10 Wonderful (53) "The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. " [](https://www.expedia.ca/Chicago-Hotels-HUGE-1700-Sqft-3bd-West-Loop-Penthouse-W-Balcony.h68751679.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/1e6ca815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/05653f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/aa5b7955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/ccf123af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LUXE 3 BR, 2 BA + Hot Tub Elmhurst 8.8/10 Excellent (33) "The house had a lot of gnats and we were bit up" CA $163 CA $407 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/f9f5b2d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, computer monitors](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/2e144bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/52c3cd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, computer monitors](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/721a7cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Theater • Game Room • Gym • Firepit • 4BR Home Belmont Cragin 7.6/10 Good (10) "Comfy beds and a great house for kids and adults." CA $94 CA $712 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-4BR-Retreat-W-Theater.h116740866.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/853ce9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/aa345e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/95fddc46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/e32db205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Home Away From Home! Calumet Heights 9.6/10 Exceptional (11) "Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. " [](https://www.expedia.ca/Chicago-Hotels-A-Home-Away-From-Home.h103943206.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109920000/109911900/109911889/83293a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109920000/109911900/109911889/d887735c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109920000/109911900/109911889/27e1aaa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109920000/109911900/109911889/71d53511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3-bedroom house in family-oriented Melrose Park. Melrose Park 10/10 Exceptional (23) "Excellent place to stay and host provided great communication. The house is very nice and we also enjoyed the fire pit and hot tub, too! We highly recommend staying at this house and we will be back soon!" [](https://www.expedia.ca/Chicago-Hotels-Cozy-3-Bedroom-House-In-Family-Oriented-Melrose-Park.h109911889.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/9d278ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/w1200h796x0y4-555fde87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/3c3ca737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/5b7a273e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3br home near Chicago, fenced yard for pets Richton Park 9.0/10 Wonderful (12) "Nice property easy check in. Experience was amazing. Thank you again " CA $316 CA $633 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Richton-Park-Hotels-Spacious-3br-Home-Near-Chicago.h108885786.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108050000/108049900/108049804/w1189h800x11y0-633ed398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/109000000/108050000/108049900/108049804/36baa0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108050000/108049900/108049804/7767f1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108050000/108049900/108049804/1243f53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG Oak Park 9.8/10 Exceptional (13) "We loved Retro House, a real treasure inside Chicago. Comfortable, quiet and safe." [](https://www.expedia.ca/Chicago-Hotels-Oak-Park-IL-Charming-Retro-2BR-CottageTrainLaundryFREE-PKG.h108049804.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/e70556b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/9904f827.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/118000000/117630000/117622400/117622336/d8d5e8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/7b164128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR Traveler\`s Favorite • Modern and Clean Belmont Cragin 10/10 Exceptional (2) "Clean, comfortable, and secure" CA $82 CA $495 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-2BR-Travelers-Favorite.h117622336.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78380000/78378300/78378272/c3de09aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78380000/78378300/78378272/0a719147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78380000/78378300/78378272/76f67267.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/79000000/78380000/78378300/78378272/5fc1bffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown Lower West Side 9.0/10 Wonderful (9) "Great" [](https://www.expedia.ca/Chicago-Hotels-Cozy-Tiny-House-1BR1BT-15-Mins-From-Chicago-Downtown.h78378272.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37150000/37146600/37146543/25a5ca04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/38000000/37150000/37146600/37146543/6db6f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37150000/37146600/37146543/86ac1098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/38000000/37150000/37146600/37146543/3a46ff3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field/Lakeview -Entire Home- Large Groups! Lakeview 10/10 Exceptional (83) "We had a fantastic experience staying here. The layout was spacious and worked perfectly for our group of 10 adults—plenty of room for everyone to relax and spread out. The home was clean, well-kept, and exactly as described. Check-in and check-out were a breeze, and the neighborhood was quiet and welcoming with easy access to public transportation, which made getting around simple. Overall, a 10/10 stay—we really enjoyed our time and would definitely book again!" [](https://www.expedia.ca/Chicago-Hotels-Wrigley-FieldLakeview-Entire-Home-Large-Groups.h37146543.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/19000000/19000000/18994300/18994215/fb7d1514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/19000000/19000000/18994300/18994215/cca1fdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/19000000/19000000/18994300/18994215/d23942d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18994300/18994215/de27a15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24 Lincoln Park 9.8/10 Exceptional (177) "Great place for our large group. Lots of room for the bridal girls to get ready for the wedding. " [](https://www.expedia.ca/Chicago-Hotels-Lincoln-Park-Single-Family-Home.h18994215.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/90a99332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/w3263h2176x1y0-9dc65f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/39dd5566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/w3264h2175x0y1-801cff6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your Next Vacation Home Des Plaines 9.6/10 Exceptional (54) "We enjoyed our stay" CA $209 CA $420 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Your-Next-Vacation-Home.h96685294.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/bf01096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/45b7296c.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/75000000/74250000/74243100/74243056/fd69f00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/5e34eeff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ✽ Charming Cottage ✽ close to College/Town/Station Wheaton 10/10 Exceptional (51) "We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!" CA $237 CA $430 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Charming-Cottage-Close-To-CollegeTownStation.h74243056.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/64000000/63940000/63935500/63935488/f4557ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/64000000/63940000/63935500/63935488/bb047552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63940000/63935500/63935488/8bd4ad5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63940000/63935500/63935488/a9cd5417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inspiring Stone Grotto Sleeps 10-20 & Free Parking Lakeview 9.8/10 Exceptional (28) "Great location that was walking distance to everything we needed. There was more than enough room for our group and it was a comfortable stay." [](https://www.expedia.ca/Chicago-Hotels-Inspiring-Stone-Grotto-Sleeps-10-20-Free-Parking.h63935488.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83280000/83277300/83277266/e87b7d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83280000/83277300/83277266/e7083f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83280000/83277300/83277266/0ef3b9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83280000/83277300/83277266/7914afce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy Chicago/suburbs 2BR townhouse fully equipped Austin 10/10 Exceptional (12) "I would recommend to anyone. " [](https://www.expedia.ca/Chicago-Hotels-Enjoy-Chicagosuburbs-2BR-Townhouse-Fully-Equipped.h83277266.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113670000/113665900/113665891/e4ceeaca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113670000/113665900/113665891/e10789cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113670000/113665900/113665891/6bf1e394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/114000000/113670000/113665900/113665891/c671a01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Home - Pool Table/Bar/Patio Skokie 10/10 Exceptional (4) "Perfect for what we needed!" CA $695 CA $1,219 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Luxury-Home-Pool-TableBarPatio.h113665891.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117480000/117470500/117470448/c81d304b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer](https://images.trvl-media.com/lodging/118000000/117480000/117470500/117470448/3a73d514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/118000000/117480000/117470500/117470448/94f53ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117480000/117470500/117470448/6f85f953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Tranquil Boho Getaway in Glen Ellyn Glen Ellyn 2.0/10 (1) "So we never stayed on this property. Or was suppose to be canceled but the host never canceled are reservation.Granted my credit card was flagged for fraud once I tried to book it, once it was cleared I tried to again, dates were not available so I told Farrah the host we needed to cancel & I will look for other places. Her response, no problem. But come to find out it wasn’t canceled, we did not stay here. Had another property in St Charles..lovely place with great communication from the host.... [](https://www.expedia.ca/Chicago-Hotels-Modern-Tranquil-Boho-Getaway-In-Glen-Ellyn.h117470448.Hotel-Information) ![8 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/4d75164f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/18072439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/f2bc5faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/dcc4c24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleeps 18 • 8BR • Game Room • Gym • Theater Portage Park 5.4/10 (3) "Great space for large groups. Park across the street is a great "feature"." CA $173 CA $1,210 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-8BR-Kids-Room.h117030296.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=2025-10-12&endDate=2025-10-13®ionId=553248635976475403&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Southwest Side Hotel Reviews ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Everything was great " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Clean room, free wine bottle and water bottles were provided daily. Great location! Everything within 15-20 minute walk. Omar, the bartender was excellent and super friendly! Had great suggestions on where to go to eat and entertainment and made great drinks! I would stay there again and great price too! " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "View was fantastic. All staff were friendly. Good location; walking distance Navy Pier." [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Great location to walk to everything " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Great hotel " [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Excellent location. The hotel was clean and the staff were friendly. The room was very small, but we knew that when we booked. " [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "The intercontinental made my trip to Chicago perfect! " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "It was a pleasurable stay" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ## Find out more about Southwest Side ## Southwest Side Vacation Homes information | Number of reviews | 572 | | --- | --- | | Accommodation | 347 Vacation Homes | | Lowest Price | CA $407 | | Highest Price | CA $1,219 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in South Englewood](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Romantic-Hotel.0-n6132347-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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