Title: Chicago 55th-56th-57th Street Station Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Chicago 55th-56th-57th Street Station Hotels](https://expedia.ca/Chicago-55th-56th-57th-Street-Station-Hotels.d6212797.Travel-Guide-Hotels)[Hyde Park Car Rentals](https://expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide)[Hyde Park Vacation Packages](https://expedia.ca/Hyde-Park.d117842.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chicago 55th-56th-57th 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 Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6212797&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6212797&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6212797&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6212797&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chicago 55th-56th-57th Street Station Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w905h683x60y0-9699e2f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w905h683x60y0-4afddd3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w904h683x60y0-a3902806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w904h683x60y0-c5e62d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 4 bedroom smart home w/ indoor fireplace Washington Park 7.8/10 Good (18) "The check in process was great and the house was very clean. It was easy to communicate with the property manager. Helped make our trip to chicago great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luke T. [](https://www.expedia.ca/Chicago-Hotels-Cheerful-4-Bedroom-Smart-Home-W-Indoor-Fireplace.h83093121.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/3b40be43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/3d83c5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/06ae3dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/ecd5dba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous historic mansion on UChicago campus. Renovation with original detail. Hyde Park 10/10 Exceptional (14) "The check-in process was effortless and the kitchen was well appointed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theophlius K. [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-Historic-Mansion-On-UChicago-Campus-Renovation-With-Original-Detail.h102659809.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/5cbec169.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) ### Lux Home in Chicago 7mins Downtown Bronzeville 9.8/10 Exceptional (27) "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) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75880000/75872400/75872313/d9384fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75880000/75872400/75872313/d3bd773d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75880000/75872400/75872313/52f65179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75880000/75872400/75872313/96e74c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodlawn Oasis...10 Minutes to Dining & Downtown Woodlawn 9.4/10 Exceptional (13) "Host was very responsive to questions and check-in/check-out instructions. Parking was easy on the street which was great. Careful on GPS directions - for some reason Google is a little off. Great for our groups C2E2 weekend. Needs a little upkeep due to what appears to have been a water leak from a drain on the 2nd floor and basement walls are showing signs of water infiltration. There is also a beeping noise we could not figure out what it was from. Suggest picking up additional flatware... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon S. [](https://www.expedia.ca/Chicago-Hotels-Woodlawn-Oasis10-Minutes-To-Dining-Downtown.h75872313.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102860000/102851700/102851653/b6066d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102860000/102851700/102851653/15851775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo, offices](https://images.trvl-media.com/lodging/103000000/102860000/102851700/102851653/9b7e7350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102851700/102851653/d6b02847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Historic Greystone - Near Lake - Free Prkg Bronzeville 7.2/10 Good (7) "House was a bit dusty didn’t match the pictures central air was not working I tried contacting host no response host was not easy to contact !!! I wouldn’t recommend this house I booked for me and my bridesmaids to stay together one day before my wedding and the house was so hot we couldn’t even get ready there " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jakira L. [](https://www.expedia.ca/Chicago-Hotels-Modern-Historic-Greystone-Near-Lake-Free-Prkg.h102851653.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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109450000/109442700/109442637/56f4d12e.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) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109450000/109442700/109442637/ac986a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins Bronzeville 9.2/10 Wonderful (10) "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) ![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) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/4738efdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop. 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) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111940000/111932600/111932512/66a6a477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111940000/111932600/111932512/92d2ae37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111940000/111932600/111932512/ef67fdaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111940000/111932600/111932512/1e66e6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Bronzeville Oasis Bronzeville [](https://www.expedia.ca/Chicago-Hotels-Charming-Bronzeville-Oasis.h111932512.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120490000/120488900/120488846/bfe664ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120490000/120488900/120488846/f57c6d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120490000/120488900/120488846/f5d03428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120490000/120488900/120488846/2f392634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-bedroom townhome in superb Chicago Kenwood [](https://www.expedia.ca/Chicago-Hotels-4-Bedroom-Townhome-In-Superb-Chicago.h120488846.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120060000/120053900/120053819/374dc9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120060000/120053900/120053819/8f94dbf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120060000/120053900/120053819/69fdd73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/121000000/120060000/120053900/120053819/29fd3bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras Woodlawn [](https://www.expedia.ca/Chicago-Hotels-Scott-House-Of-Woodlawn-Charming-3-Bedroom-House-In-Amazing-Chicago-With-AC.h120053819.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112680000/112676000/112675916/5b84201f.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/113000000/112680000/112676000/112675916/30930035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/113000000/112680000/112676000/112675916/cf104660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112680000/112676000/112675916/2c8c06e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood South Shore [](https://www.expedia.ca/Chicago-Hotels-Remote-Worker-Special-2-Bedroom-Townhome-In-Jackson-Park-Highlands-Neighborhood.h112675916.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=2025-11-17&endDate=2025-11-18®ionId=6212797&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FChicago-55th-56th-57th-Street-Station-Private-Vacation-Homes.d6212797-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChicago-55th-56th-57th-Street-Station-Private-Vacation-Homes.d6212797-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chicago 55th-56th-57th Street Station Hotel Reviews ![Best Western Grant Park Hotel](//images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg) ### Best Western Grant Park Hotel 10/10 Excellent "Very comfortable and clean rooms, centrally located, and an excellent bakery!" [](https://expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](//images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "Clean, nice appointments, friendly staff" [](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Kasa South Loop Chicago](//images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/603af13d_y.jpg) ### Kasa South Loop Chicago 10/10 Excellent "This property was so amazing! Very clean, great communication from the host and an amazing and safe neighborhood. My partner and I walked to most of our tourist attractions and felt very safe! There are so many restaurants and cafe around to visit. Would highly recommend 10/10" [](https://expedia.ca/Chicago-Hotels-Kasa-South-Loop-Chicago.h29433443.Hotel-Information) ![HI Chicago Hostel](//images.trvl-media.com/lodging/4000000/3970000/3965000/3964916/9bea5a17_y.jpg) ### HI Chicago Hostel 10/10 Excellent "Central location , clean rooms , comfortable " [](https://expedia.ca/Chicago-Hotels-HI-Chicago.h3964916.Hotel-Information) ![Congress Plaza Hotel](//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) ![Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/21200/21142/886bf093_y.jpg) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel 10/10 Excellent "Overall the rooms are quiet and the checkin is easy." [](https://expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![Hilton Garden Inn Chicago Downtown South Loop](//images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773_y.jpg) ### Hilton Garden Inn Chicago Downtown South Loop 10/10 Excellent "Very friendly staff. Hotel was kept well. Lots of things to do in the area." [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![Travelodge by Wyndham Downtown Chicago](//images.trvl-media.com/lodging/1000000/200000/197000/196959/b675990c_y.jpg) ### Travelodge by Wyndham Downtown Chicago 10/10 Excellent "Very spacious room" [](https://expedia.ca/Chicago-Hotels-Travelodge-By-Wyndham-Downtown-Chicago.h196959.Hotel-Information) ![The Buckingham Hotel](//images.trvl-media.com/lodging/2000000/1120000/1112300/1112252/fbb6f786_y.jpg) ### The Buckingham Hotel 10/10 Excellent "Safe , clean & very secure. " [](https://expedia.ca/Chicago-Hotels-The-Buckingham-Hotel.h1112252.Hotel-Information) ## Find out more about Chicago 55th-56th-57th Street Station #### What types of Vacation Homes can I find in Chicago 55th-56th-57th Street Station? When you’re looking for Chicago 55th-56th-57th Street Station Vacation Homes in 2025, 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 55th-56th-57th 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 55th-56th-57th Street Station. #### How much do Vacation Homes cost in Chicago 55th-56th-57th Street Station? Prices for Chicago 55th-56th-57th Street Station Vacation Homes can start from as little as \* in 2025. 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 55th-56th-57th Street Station, as well as how high the demand for accommodation is near Chicago 55th-56th-57th 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 55th-56th-57th 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 55th-56th-57th Street Station Vacation Homes? Expedia’s search function can help you find a great deal on Chicago 55th-56th-57th Street Station Vacation Homes. Changing the sort order of your search results can help you to find cheap Vacation Homes in Chicago 55th-56th-57th 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 55th-56th-57th Street Station Vacation Homes? One of the many benefits of booking Chicago 55th-56th-57th 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 55th-56th-57th 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 55th-56th-57th Street Station Vacation Homes? It’s often possible to change or cancel bookings at Chicago 55th-56th-57th 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 55th-56th-57th 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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