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Compare 260 Vacation Homes in Roosevelt Station with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (90)
"We had a wonderful visit in Chicago and this VRBO was a great place to stay for our group. There are plenty of bedrooms and bathrooms and it is close to all the restaurants, bars, and an El stop. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

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

9.4 out of 10, Exceptional, (13)
"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

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (54)
"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

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

9.4 out of 10, Exceptional, (93)
"Spacious property. Plenty of room and great neighborhood. Wish the larger TV was upstairs. "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Beautiful, Remodeled Penthouse Unit in Old Town!

9.2 out of 10, Wonderful, (22)
"Super nice property, and the host was so helpful and kind. Super happy with the house overall, would recommend! "
Beautiful, Remodeled Penthouse Unit in Old Town!

Spectacular NEW Penthouse - Pool, Fireplace, Incredible Views, Top Location

10.0 out of 10, Exceptional, (6)
Spectacular NEW Penthouse - Pool, Fireplace, Incredible Views, Top Location

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (14)
"Very convenient to the EL and the zoo. Large clean space. Perfect for a family trip"
Luxury SOHO Styled Two-Level Townhouse - Old Town

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (45)
"Fantastic house…whole family enjoyed our stay. Thank you!"
Luxury House in the heart of Old Town with Parking

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Prime location Historic Chicago Townhouse

9.4 out of 10, Exceptional, (70)
"Always love coming here with family . Perfect location for playing in the city. Great space for togetherness and also time apart."
Prime location Historic Chicago Townhouse

51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

10.0 out of 10, Exceptional, (187)
"Outstanding location. Very spacious and top notch. I highly recommend the penthouses. "
51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

50th Floor MagMile forever VIEWS, Balcony, Pool

10.0 out of 10, Exceptional, (24)
"We had a terrific stay at this property. Great location, amazing views. Grocery store next door was a nice bonus. Glad we found you!"
50th Floor MagMile forever VIEWS, Balcony, Pool

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

10.0 out of 10, Exceptional, (20)
"Great place! "
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Downtown Goose Island with access to patio - 1

9.2 out of 10, Wonderful, (5)
"This property is perfect for those on a budget but still want a great location in the city of Chicago, the photo description of the property was slightly off, we were told there would be a bunk bed and pull out couch (per the photos and description) but neither were present at the property. The property was clean especially the kitchen and bathroom but there we saw ants on the floor and a few other bugs that grossed us out, If you are expecting some luxury stay this is not the place for you, it...
Downtown Goose Island with access to patio - 1

2 Connecting Suites at a 4⭐️ Hotel

The price is AED 2,036
AED 2,714 total
includes taxes & fees
22 Jun - 23 Jun
2 Connecting Suites at a 4⭐️ Hotel

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

10.0 out of 10, Exceptional, (20)
"My coworkers and I had a wonderful time at this perfectly located property. The property had plenty of privacy, charming At CB textural character, and was perfectly located for shopping and dining. Would definitely stay here again!"
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

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

10.0 out of 10, Exceptional, (57)
"Excellent property, excellent location, excellent host!"
Spacious 4-Level/4-Bedroom Townhouse in West Loop

Stunning Condo #2 - Downtown River North!

9.6 out of 10, Exceptional, (18)
"Beautiful condo on the River North end of the loop. We loved our stay!"
Stunning Condo #2 - Downtown River North!

Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

10.0 out of 10, Exceptional, (29)
"Located in a nice part of town. Right next to the highway but you can barely hear any street noise from inside. Comfy beds, easy communication with owner. Located near a couple nice bars and restaurants that are walkable and the blue line is also really close. Plan on staying here again in the future!"
Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

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

10.0 out of 10, Exceptional, (90)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
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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