Title: Chicago 27th Street Station Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Bronzeville Travel Guide](https://expedia.ca/Chicago-Bronzeville.dx6132245)[Chicago 27th Street Station Hotels](https://expedia.ca/Chicago-27th-Street-Station-Hotels.d6212781.Travel-Guide-Hotels)[Bronzeville Car Rentals](https://expedia.ca/Car-Rentals-In-Bronzeville.d6132245.Car-Rental-Guide)[Bronzeville Vacation Packages](https://expedia.ca/Bronzeville.d6132245.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chicago 27th Street Station Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6212781&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6212781&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6212781&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 four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6212781&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chicago 27th Street Station Vacation Homes ![Smart TV](https://images.trvl-media.com/lodging/119000000/118680000/118678600/118678522/797f1389.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118680000/118678600/118678522/6914fdd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118680000/118678600/118678522/c7e10092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118680000/118678600/118678522/429344f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side 8.8/10 Excellent (3) "Communication from host. Amenities. Work out center" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue R. [](https://www.expedia.ca/Chicago-Hotels-Spacious-2BR-Group-Stay-Near-McCormick-Wintrust.h118678522.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/61384769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/2dbb2fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/e98f11dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/f359b69d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 9.8/10 Exceptional (28) "Larry was super responsive, the property was spotless, the location perfect. Our group of friends loved it. We will be back! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle B. [](https://www.expedia.ca/Chicago-Hotels-Lux-Home-In-Chicago-7mins-Downtown.h90679258.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/cd4b36ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/9ba595c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/1d8cadd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library, stereo](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/w5782h4000x218y0-e659d3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 10/10 Exceptional (1) "The property was clean. The house was nice and neat. I enjoyed my stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lamyha S. [](https://www.expedia.ca/Chicago-Hotels-Bronzeville-Jazz-Room-Beautiful.h121703532.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66900000/66900000/66899944/a1309287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/67000000/66900000/66900000/66899944/9e847387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66900000/66900000/66899944/57657e01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/67000000/66900000/66900000/66899944/c202d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chinatown 9.8/10 Exceptional (10) "Not one of these fancy, interior-design-focused places by any means, but the beds and pillows were very comfortable, great water pressure, high quality keurig and appliances, and an incredible incredible location. Highly recommended." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle T. [](https://www.expedia.ca/Chicago-Hotels-1-23-4-Bedroom-Condo-McCormick-Place.h66899944.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/108000000/107440000/107431400/107431367/22b2ed92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107440000/107431400/107431367/f652ebf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107440000/107431400/107431367/1384d1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107440000/107431400/107431367/ca4f71a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side [](https://www.expedia.ca/Chicago-Hotels-Family-Friendly-South-Loop-Escape-By-RedAwning.h107431367.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/7486dedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/40a5fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/w2686h2011x2y3-3f3595f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/w1320h1248x0y1-c2adfd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bridgeport 9.4/10 Exceptional (21) "The owners were SUPER helpful and their communication was SUPERB!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juan B. [](https://www.expedia.ca/Chicago-Hotels-Elegant-Mayors-Manor-In-Central-Chicago-9-Beds.h94721307.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87670000/87663200/87663133/w507h683x258y0-cae720ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87670000/87663200/87663133/w377h683x324y0-e0317d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/88000000/87670000/87663200/87663133/w904h683x60y0-05d3c7b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87670000/87663200/87663133/w507h639x258y44-48406d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 9.8/10 Exceptional (8) "Overall great stay, great host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyrese M. [](https://www.expedia.ca/Chicago-Hotels-Lakefront-Property.h87663133.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95032600/95032535/df4d21cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/96000000/95040000/95032600/95032535/b27b1e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95040000/95032600/95032535/066a885d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95032600/95032535/b3566013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 9.2/10 Wonderful (20) "The house was beautiful and check-in was easy. It was a great place for my family to gather and spend time together. There was plenty of room for everyone and the kitchen was a delight to work in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda P. [](https://www.expedia.ca/Chicago-Hotels-Renovated-6-Bedroom-5-Bathroom-Home-10-Minutes-From-Downtown-Chicago.h95032535.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101870000/101862400/101862365/de00b0b5_edited_99ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101870000/101862400/101862365/03d666f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101870000/101862400/101862365/a752bb74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/102000000/101870000/101862400/101862365/25339a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 9.4/10 Exceptional (3) "Good stay close to a lot of bus stops very convenient for what we did on our trip. The host was very accommodating and left great instructions on how to access the home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen M. [](https://www.expedia.ca/Chicago-Hotels-Hamaline-Luxury-Home-Guest-House.h101862365.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68870000/68865600/68865544/w905h683x60y0-c4009c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/69000000/68870000/68865600/68865544/81e07e27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/69000000/68870000/68865600/68865544/52536f24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/69000000/68870000/68865600/68865544/ff9fc64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chinatown 9.8/10 Exceptional (9) "Just off the red line. Plenty of great food near by" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve C. [](https://www.expedia.ca/Chicago-Hotels-1-31-4-Bedroom-Condo-McCormick-Place.h68865544.Hotel-Information) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66910000/66900500/66900441/w905h683x60y0-829f4e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66910000/66900500/66900441/w905h683x60y0-70d84962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66910000/66900500/66900441/w1024h594x0y47-9211483e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/67000000/66910000/66900500/66900441/w905h683x60y0-3673eb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Armour Square 9.2/10 Wonderful (13) "Enjoyed the neighborhood " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole P. [](https://www.expedia.ca/Chicago-Hotels-4-2N-4-Bedroom-4-Bath-Condo-McCormick-Place.h66900441.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118310000/118306400/118306309/944a161b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118310000/118306400/118306309/71d8798a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118310000/118306400/118306309/8b1d4a7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/119000000/118310000/118306400/118306309/032ea855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side 9.4/10 Exceptional (3) "We enjoyed our weekend in Chicago. Location was easy to get to from the airports, building was secure and the host was great to work with. Great place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg F. [](https://www.expedia.ca/Chicago-Hotels-Spacious-2BR-Unit-Skyline-View-Walk-To-McCormick.h118306309.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/116000000/115460000/115457900/115457865/4ed8bac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115460000/115457900/115457865/fe607de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/116000000/115460000/115457900/115457865/f21c6e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115460000/115457900/115457865/27b9b4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 10/10 Exceptional (6) "We were preparing for our organizations annual fundraiser gala. This home was absolutely amazing. The space was appreciated. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy M. [](https://www.expedia.ca/Chicago-Hotels-Modern-4-Bed.h115457865.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118680000/118676800/118676738/02ce6a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118680000/118676800/118676738/be505a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118680000/118676800/118676738/d880f659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118680000/118676800/118676738/35e02660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side [](https://www.expedia.ca/Chicago-Hotels-McCormick-3B2Ba-Corner-Oasis-For-Up-To-10-Guests.h118676738.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109650000/109642800/109642796/e4e1127d.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/110000000/109650000/109642800/109642796/55e4cbc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109650000/109642800/109642796/e22a2373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109650000/109642800/109642796/6d0fc6a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 7.6/10 Good (4) "The place was nice!!!! Joseph( Host) Has great communication skills!!!! The place felt like a nice hideout getaway and nice neighborhood. I would love to come back. Thanks for the stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dante' M. [](https://www.expedia.ca/Chicago-Hotels-Breeze-Of-Bronzeville-Chicago-3-Bedroom-2-Bath-9-Mins-From-Downtown-Chicago.h109642796.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109450000/109442700/109442637/f592b2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109450000/109442700/109442637/50349115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109450000/109442700/109442637/94db069f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109450000/109442700/109442637/56f4d12e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Bronzeville 9.4/10 Exceptional (11) "Property matched the pictures perfectly! Loved the updates and appreciated the abundance of towels, dishes, etc! 3rd floor walkup if thats an issue for you. Also felt safe and secure. Great neighborhood too! Host provided detailed, easy to understand instructions for the property and was accessible via the VRBO app! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marquita S. [](https://www.expedia.ca/LuxHome-Up-To-8-Guests-In-Chicago-WiFi.h109442637.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/921c4956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/a81ea36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/0a273faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/c70535a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kenwood 6.0/10 (2) "Great property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Chicago-Hotels-Ahh-Mazing-Home.h92064395.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299236/2fcdf218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299236/a6e9bf47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299236/00768d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299236/6683edb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side [](https://www.expedia.ca/Chicago-Hotels-Modern-3BR-Near-McCormick-South-Loop.h122299236.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299245/1072f4ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299245/31aa9a97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299245/2d38e060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299245/086a5a2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side [](https://www.expedia.ca/Chicago-Hotels-Spacious-3BR-Urban-Getaway-W-Gym.h122299245.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299227/fc35c55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299227/1c7d8fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299227/5e15eb63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122300000/122299300/122299227/406b957f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Near South Side [](https://www.expedia.ca/Chicago-Hotels-Stylish-3BR-Gem-In-Prime-Location.h122299227.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=2025-12-19&endDate=2025-12-20®ionId=6212781&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chicago+27th+Street+Station%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6212781&latLong=41.844077%2C-87.613309&adults=2&startDate=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chicago+27th+Street+Station%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6212781&latLong=41.844077%2C-87.613309&adults=2&startDate=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chicago+27th+Street+Station%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6212781&latLong=41.844077%2C-87.613309&adults=2&startDate=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chicago+27th+Street+Station%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6212781&latLong=41.844077%2C-87.613309&adults=2&startDate=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=VILLA) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chicago+27th+Street+Station%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6212781&latLong=41.844077%2C-87.613309&adults=2&startDate=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chicago+27th+Street+Station%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6212781&latLong=41.844077%2C-87.613309&adults=2&startDate=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=VACATION_HOME) ![](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%2FChicago-27th-Street-Station-Private-Vacation-Homes.d6212781-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChicago-27th-Street-Station-Private-Vacation-Homes.d6212781-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chicago 27th Street Station Hotel Reviews ![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 "Beautiful hotel. Great bedroom/bathroom layout and decor. Comfortable bed! Great bathroom toiletries and amenities. Beautiful rooftop bar. Lobby bar live entertainment. Very nice and clear fitness facility! " [](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.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 "great stay" [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "The staff was wonderful, and my room was neat and clean. My stay was very good." [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.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 "Great" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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" [](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 "Todo maravilloso, las habitaciones con black out impecable, excelente atención y ubicación. El desayuno, no habrá mejor desayuno que encuentres en otro hotel. La atención de Milaidy en el restaurante fue otro nivel. Regresaría siempre. " [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg) ### Silversmith Hotel Chicago Downtown 10/10 Excellent "Very courteous, helpful staff. Nice rooms and layout. " [](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "We had a great stay and will be back again." [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "The room was very clean. " [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ## Find out more about Chicago 27th Street Station #### What types of Vacation Homes can I find in Chicago 27th Street Station? When you’re looking for Chicago 27th Street Station Vacation Homes in 2026, you can use Expedia’s filters to find accommodation that’s family-friendly or business-friendly, and narrow down your search results by amenities, price per night, and much more. For example, you can search for Vacation Homes that welcome pets, or one with accessibility features. You’ll find a range of places to stay to suit every budget, so if you're looking for cheap Vacation Homes in Chicago 27th Street Station, use our simple search function to help you secure a good deal. If the exact location of Vacation Homes is important to you, try our map facility to view available places in relation to each other and to Chicago 27th Street Station. #### How much do Vacation Homes cost in Chicago 27th Street Station? Prices for Chicago 27th Street Station Vacation Homes can start from as little as \* in 2026\. The cost per night varies depending on several factors, including the amenities on offer at Vacation Homes, the exact location of Vacation Homes and how far they are from Chicago 27th Street Station, as well as how high the demand for accommodation is near Chicago 27th Street Station on the dates of your booking. At Expedia, we cater for every budget, so if you’re looking for cheap Vacation Homes in Chicago 27th Street Station, you can sleep easy knowing that we’ll help you to secure some of the very best deals on offer. #### How to find the best deals on Chicago 27th Street Station Vacation Homes? Expedia’s search function can help you find a great deal on Chicago 27th Street Station Vacation Homes. Changing the sort order of your search results can help you to find cheap Vacation Homes in Chicago 27th Street Station at a glance. If you have a specific price range in mind, try selecting minimum and maximum prices per night to narrow your results. You can also filter by guest ratings and star ratings to find some of the best offers for Vacation Homes within your budget. Don’t forget, if you’re an Expedia Rewards member, you can use the ‘Member Prices’ filter to make instant savings on your booking. #### Why should I choose Expedia to book Chicago 27th Street Station Vacation Homes? One of the many benefits of booking Chicago 27th Street Station Vacation Homes with Expedia is the clear and simple search function. When you use the many filters on offer, you can easily compile a shortlist of fantastic places to stay, and make comparisons between the different Vacation Homes so that you can choose exactly what you need. At Expedia, it’s possible to create your own customized package and make great savings by booking flights, car hire, and more at the same time as Chicago 27th Street Station Vacation Homes. And don’t forget that with free membership to Expedia Rewards, you can earn points on all eligible purchases, and build your points total to use towards future travel. #### What is the cancellation policy on booking Chicago 27th Street Station Vacation Homes? It’s often possible to change or cancel bookings at Chicago 27th Street Station Vacation Homes without a fee, but it depends on the rules and restrictions of the various Vacation Homes. Many booking options offer a window of flexibility, for example a full refund if you cancel more than 24 or 48 hours before Chicago 27th Street Station arrival dates. It’s best to check the policies of the individual Vacation Homes before making a booking, if flexibility is important to you. You can filter for the ‘Fully refundable’ payment type when you search for Vacation Homes. You can also view the terms of the different Vacation Homes at any time by checking the details of your booking at Expedia. \*Prices and availability are subject to change. 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