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Vacation Homes in Chicago 55th-56th-57th Street Station

Cheerful 4 bedroom smart home w/ indoor fireplace
7.8 out of 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
Luke T.
Cheerful 4 bedroom smart home w/ indoor fireplace
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
10.0 out of 10, Exceptional, (14)
"The check-in process was effortless and the kitchen was well appointed."
United States
Theophlius K.
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Lux Home in Chicago 7mins Downtown
9.8 out of 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
Kyle B.
Lux Home in Chicago 7mins Downtown
Woodlawn Oasis...10 Minutes to Dining & Downtown
9.4 out of 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
Jon S.
Woodlawn Oasis...10 Minutes to Dining & Downtown
Modern Historic Greystone - Near Lake - Free Prkg
7.2 out of 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
Jakira L.
Modern Historic Greystone - Near Lake - Free Prkg
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
9.2 out of 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
Marquita S.
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.
6.0 out of 10, (2)
"Great property"
United States
Anonymous traveler
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.
Charming Bronzeville Oasis
Charming Bronzeville Oasis
4-bedroom townhome in superb Chicago
4-bedroom townhome in superb Chicago
Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras
Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
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.
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Top Chicago 55th-56th-57th Street Station Hotel Reviews

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?

At Expedia, you’ll find great Chicago 55th-56th-57th Street Station Vacation Homes for your family vacation, business trip, romantic weekend break, and more. If you’re planning a vacation with kids, try using the traveler experience filter to select “Family-friendly” Chicago 55th-56th-57th Street Station Vacation Homes. Or, if you’re traveling for work, you can check the “Business-friendly” box to find business-oriented places to stay in Chicago 55th-56th-57th Street Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Chicago 55th-56th-57th Street Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Chicago 55th-56th-57th Street Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Chicago 55th-56th-57th Street Station?

The price per night for Chicago 55th-56th-57th Street Station Vacation Homes in 2025 can start from as low as *. The cost of Vacation Homes varies depending on a number of factors: the dates of your stay, the exact location of the accommodation, and whether there are any special events taking place near Chicago 55th-56th-57th Street Station, to name just three. When there’s a high demand for rooms in Chicago 55th-56th-57th Street Station, this can cause prices to increase, whereas traveling during a quieter time of the year can mean lower prices. Booking through Expedia can help you find some of the best deals for cheap Vacation Homes in Chicago 55th-56th-57th Street Station, so you can sleep easy without going over your budget.

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Expedia’s search function can help you find some of the best deals on Chicago 55th-56th-57th Street Station Vacation Homes. You can select a minimum and maximum price per night according to your budget, and filter by guest ratings and star ratings to ensure you find the right Vacation Homes for your needs. Changing the sort order according to price can also help you to view cheap Vacation Homes in Chicago 55th-56th-57th Street Station at a glance, and you can combine this with our own picks to highlight some of the best available offers. Don’t forget, if you’re an Expedia Rewards member, you can use the “Member Prices” filter to make extra savings on your booking.

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Booking with Expedia allows you to browse a wide selection of places to stay in Chicago 55th-56th-57th Street Station, complete with search filters that make it easy to locate Vacation Homes that best meet your specific requirements. Our clear and easy-to-use search function makes it effortless to compare amenities, prices, property types, neighborhoods, and much more. At Expedia, you can also find flights, car rental, and activities, and you can combine your bookings for greater savings. Plus, Expedia Rewards members accrue points on all eligible purchases. Build your points total to gain discounts on subsequent bookings in the future. Membership is free, so go ahead and join.

What is the cancellation policy on booking Chicago 55th-56th-57th Street Station Vacation Homes?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Chicago 55th-56th-57th Street Station Vacation Homes with a full refund, depending on the rules and restrictions. For example, some Vacation Homes may not give refunds if you cancel your booking within 24 or 48 hours of your arrival date, and some bookings are non-refundable. Be sure to view the policies provided by the Chicago 55th-56th-57th Street Station Vacation Homes, and confirm the exact cancellation window on your selected location’s details page. If free cancellation is important to you, you can filter for the “Fully refundable” payment type when you search for your Vacation Homes.

*Prices and availability are subject to change. Additional terms may apply 

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