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

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

Our top choices for Chicago 55th-56th-57th Street Station vacation homes

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.6 out of 10, Exceptional, (7)
"Nice place. Looks freshly updated. If you have a hard time with stairs this probably isnt for you as there is 2 flights to climb. Other than that great place"
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very Good, (16)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Modern Historic Greystone - Near Lake - Free Prkg

7.0 out of 10, Good, (6)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Modern Historic Greystone - Near Lake - Free Prkg

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (23)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (12)
"This was a beautiful well appointed home with much unique artwork and well appointed furnishings. It was very welcoming. The area was very walkable to everything we needed and the outside area was very pleasant. The extra bedrooms and bathrooms made it very comfortable for our Sister group of six. "
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (12)
"I would book the house again"
Woodlawn Oasis...10 Minutes to Dining & Downtown

Walk to Chicago's Shops & Eats: Bronzeville Duplex

Walk to Chicago's Shops & Eats: Bronzeville Duplex

Beautiful newly renovated townhome, very quite, safe, centralized location.

Beautiful newly renovated townhome, very quite, safe, centralized location.

Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.

6.0 out of 10, (2)
"Great property"
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.

Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood

Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood

Charming Bronzeville Oasis

Charming Bronzeville Oasis
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

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.

How to find the best deals on Chicago 55th-56th-57th Street Station Vacation Homes?

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.

Why should I choose Expedia to book Chicago 55th-56th-57th Street Station Vacation Homes?

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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