Title: Chicago 59th Street Station Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Chicago 59th Street Station Hotels](https://expedia.ca/Chicago-59th-Street-Station-Hotels.d6212800.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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chicago 59th 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 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6212800&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6212800&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6212800&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 four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6212800&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chicago 59th Street Station vacation homes ![Interior](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/f359b69d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/d4093f56.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) ![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 [](https://www.expedia.ca/Chicago-Hotels-Lux-Home-In-Chicago-7mins-Downtown.h90679258.Hotel-Information) 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) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/a83a4221.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) ![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) ![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) ### Cheerful 4 bedroom smart home w/ indoor fireplace [](https://www.expedia.ca/Chicago-Hotels-Cheerful-4-Bedroom-Smart-Home-W-Indoor-Fireplace.h83093121.Hotel-Information) Washington Park 8.0/10 Very good (19) "Conveniently located just south of downtown. The space was cavernous! Plenty of room and stylishly decorated. Good communication from the host throughout our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](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/103000000/102660000/102659900/102659809/60e9c2e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/0c2f909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/7d5626af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/587528e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous historic mansion on UChicago campus. Renovation with original detail. [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-Historic-Mansion-On-UChicago-Campus-Renovation-With-Original-Detail.h102659809.Hotel-Information) Hyde Park 10/10 Exceptional (15) "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) ![Interior](https://images.trvl-media.com/lodging/76000000/75880000/75872400/75872313/544455c5.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) ![Interior](https://images.trvl-media.com/lodging/76000000/75880000/75872400/75872313/292fc8d3.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) ### Woodlawn Oasis...10 Minutes to Dining & Downtown [](https://www.expedia.ca/Chicago-Hotels-Woodlawn-Oasis10-Minutes-To-Dining-Downtown.h75872313.Hotel-Information) Woodlawn 9.2/10 Wonderful (14) "I would book the house again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilyn W. [](https://www.expedia.ca/Chicago-Hotels-Woodlawn-Oasis10-Minutes-To-Dining-Downtown.h75872313.Hotel-Information) ![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) ![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/110000000/109450000/109442700/109442637/2dcd2570.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 [](https://www.expedia.ca/LuxHome-Up-To-8-Guests-In-Chicago-WiFi.h109442637.Hotel-Information) 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) ![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) ![Dining](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/15c20ef7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/1f7a0006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92070000/92064400/92064395/009337c0.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. [](https://www.expedia.ca/Chicago-Hotels-Ahh-Mazing-Home.h92064395.Hotel-Information) 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) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120060000/120053900/120053819/6bb7460e.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120060000/120053900/120053819/69fdd73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras [](https://www.expedia.ca/Chicago-Hotels-Scott-House-Of-Woodlawn-Charming-3-Bedroom-House-In-Amazing-Chicago-With-AC.h120053819.Hotel-Information) Woodlawn [](https://www.expedia.ca/Chicago-Hotels-Scott-House-Of-Woodlawn-Charming-3-Bedroom-House-In-Amazing-Chicago-With-AC.h120053819.Hotel-Information) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120490000/120488900/120488846/45b9ae4a.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 [](https://www.expedia.ca/Chicago-Hotels-4-Bedroom-Townhome-In-Superb-Chicago.h120488846.Hotel-Information) Kenwood [](https://www.expedia.ca/Chicago-Hotels-4-Bedroom-Townhome-In-Superb-Chicago.h120488846.Hotel-Information) ![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) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111940000/111932600/111932512/66a6a477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111940000/111932600/111932512/b01dd36f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Bronzeville Oasis [](https://www.expedia.ca/Chicago-Hotels-Charming-Bronzeville-Oasis.h111932512.Hotel-Information) Bronzeville [](https://www.expedia.ca/Chicago-Hotels-Charming-Bronzeville-Oasis.h111932512.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/113000000/112680000/112676000/112675916/1829ef9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112680000/112676000/112675916/5b84201f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/113000000/112680000/112676000/112675916/a6dfee7f.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) ### Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood [](https://www.expedia.ca/Chicago-Hotels-Remote-Worker-Special-2-Bedroom-Townhome-In-Jackson-Park-Highlands-Neighborhood.h112675916.Hotel-Information) 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=2025-12-27&endDate=2025-12-28®ionId=6212800&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-59th-Street-Station-Private-Vacation-Homes.d6212800-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChicago-59th-Street-Station-Private-Vacation-Homes.d6212800-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chicago 59th Street Station Hotel Reviews ![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/de4336b3_y.jpg) ### Le Méridien Essex Chicago 10/10 Excellent "Great front desk staff" [](https://expedia.ca/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.Hotel-Information) ![Hilton Garden Inn Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773_y.jpg) ### Hilton Garden Inn Chicago Downtown South Loop 10/10 Excellent "Great space " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Everything is good " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Homewood Suites by Hilton Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2d5c8626_y.jpg) ### Homewood Suites by Hilton Chicago Downtown South Loop 10/10 Excellent "Nice new hotel, everything updated. Comfortable. Convenient location. " [](https://expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information) ![Kasa South Loop Chicago](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/603af13d_y.jpg) ### Kasa South Loop Chicago 10/10 Excellent "Great apartment, great view, close to good amenities, very safe." [](https://expedia.ca/Chicago-Hotels-Kasa-South-Loop-Chicago.h29433443.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "From the moment we checked in, this was one of my best hotel experiences ever. I'm a Chicago native leaving abroad, and my partner and I would definitely stay here again. Love the neighborhood and this hotel is a great addition." [](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Home2 Suites by Hilton Chicago McCormick Place](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114548/39f1f0c8_y.jpg) ### Home2 Suites by Hilton Chicago McCormick Place 10/10 Excellent "Location, very spacious rooms, great breakfast!!! Excellent customer service!!! Will be staying there again. " [](https://expedia.ca/Chicago-Hotels-Home2-Suites-By-Hilton-Chicago-McCormick-Place.h20114548.Hotel-Information) ![Hampton Inn Chicago McCormick Place](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251274/5c2508de_y.jpg) ### Hampton Inn Chicago McCormick Place 10/10 Excellent "Very nice hotel " [](https://expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-McCormick-Place.h23251274.Hotel-Information) ![Sentral Michigan Avenue](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a_y.jpg) ### Sentral Michigan Avenue 10/10 Excellent "Beautiful view, and a very nice condo. " [](https://expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information) ## Find out more about Chicago 59th Street Station #### What types of Vacation Homes can I find in Chicago 59th Street Station? When you’re looking for Chicago 59th 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 59th 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 59th Street Station. #### How much do Vacation Homes cost in Chicago 59th Street Station? Prices for Chicago 59th 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 59th Street Station, as well as how high the demand for accommodation is near Chicago 59th 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 59th 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 59th Street Station Vacation Homes? Expedia’s search function can help you find a great deal on Chicago 59th Street Station Vacation Homes. Changing the sort order of your search results can help you to find cheap Vacation Homes in Chicago 59th 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 59th Street Station Vacation Homes? One of the many benefits of booking Chicago 59th 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 59th 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 59th Street Station Vacation Homes? It’s often possible to change or cancel bookings at Chicago 59th 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 59th 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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