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Vacation Homes in Roosevelt Station

Our top choices for Roosevelt Station vacation homes

Historic luxury townhouse on Chicago's Gold Coast

9.4 out of 10, Exceptional, (74)
"Large houseClean and well furnishedMix-up on checkin but manager on site fixed quickly.I highly recommend and would stay here again"
Historic luxury townhouse on Chicago's Gold Coast

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (90)
"Awesome location, plenty of space, timely communication, clean. We loved it!"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.2 out of 10, Wonderful, (17)
"Very quiet and close to CTA , Old Town easy access to the city"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

10.0 out of 10, Exceptional, (22)
"Great place! "
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.8 out of 10, Exceptional, (100)
"Loved being able to walk to Second City, Jeni’s, and grocery store. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (58)
"Plenty of space for our large group, great location and timely communication from host. We were able to walk to nearby restaurants and bars. Would stay again. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.8 out of 10, Exceptional, (15)
"This place was great! In a really nice area of Chicago too. "
$581 nightly
The price is $687
Sep 16 - Sep 17
Total with taxes and fees
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (50)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (98)
"Good for our get together."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

10.0 out of 10, Exceptional, (2)
"We had a great stay! Inna provided us all the info we needed to check in smoothly when we arrived and the garage spot made it easy for us to park and unload luggage straight into the house. Everything was super clean! The house is big enough that even with so many guests everyone felt spread out and had their own space. We were able to take a 5ish min walk to the beach which was such a bonus! "
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

9.8 out of 10, Exceptional, (23)
"Loved everything. A great place to gather family."
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (16)
"Very convenient to the EL and the zoo. Large clean space. Perfect for a family trip"
Luxury SOHO Styled Two-Level Townhouse - Old Town

Spacious 4-Level/4-Bedroom Townhouse in West Loop

10.0 out of 10, Exceptional, (58)
"We really loved staying at this property. I would definitely book this again. Very clean and comfortable."
Spacious 4-Level/4-Bedroom Townhouse in West Loop

Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests

10.0 out of 10, Exceptional, (2)
"Stayed in Chicago for a trade show. Great location and well kept property "
Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests

Stunning Condo #2 - Downtown River North!

9.6 out of 10, Exceptional, (18)
"We loved the proximity to the City and access to the CTA!! "
Stunning Condo #2 - Downtown River North!

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

10.0 out of 10, Exceptional, (3)
"We enjoyed our stay great host "
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views

10.0 out of 10, Exceptional, (3)
"Clean, spacious, and well equipped for renters. Our group enjoyed this home immensely and its easy walk to all Fulton Market attractions. Owner is thoughtful and very responsive. I hope to stay again next time I'm in the area!"
Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views

Centrally Located Chicago Townhome

Centrally Located Chicago Townhome

NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage

NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage

The Hide-Away | South Loop Apartment

The Hide-Away | South Loop Apartment
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 Roosevelt Station Hotel Reviews

Find out more about Roosevelt Station

Find out more about Roosevelt Station

What types of Vacation Homes can I find in Roosevelt Station?

At Expedia, you’ll find great Roosevelt 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” Roosevelt 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 Roosevelt Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Roosevelt Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Roosevelt Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Roosevelt Station?

The price per night for Roosevelt 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 Roosevelt Station, to name just three. When there’s a high demand for rooms in Roosevelt 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 Roosevelt Station, so you can sleep easy without going over your budget.

How to find the best deals on Roosevelt Station Vacation Homes?

Expedia’s search function can help you find some of the best deals on Roosevelt 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 Roosevelt 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 Roosevelt Station Vacation Homes?

Booking with Expedia allows you to browse a wide selection of places to stay in Roosevelt 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 Roosevelt Station Vacation Homes?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Roosevelt 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 Roosevelt 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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