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Compare 226 Vacation Homes in Roosevelt Station with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (88)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

858 Orleans

3.0 star property
858 Orleans

811 N. Sedgwick

3.5 star property
811 N. Sedgwick

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (41)
"Beautiful property, wonderful location, ideal for a family weekend in Chicago with close proximity to the lake, Loop, Lincoln Park and Old Town. Mo is a terrific host. Highly recommend!"
Luxury House in the heart of Old Town with Parking

Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom

10.0 out of 10, Exceptional, (1)
Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom

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

9.4 out of 10, Exceptional, (83)
"This property worked well for our group of 14. The need to go outside to get between the upper and lower levels had been made very clear. It was a bit tricky at first with 5 young children, but we all adjusted pretty quickly. The lower level is more basic than upstairs but still worked very well for 5 of the group. The neighborhood was perfect for the location of the wedding we were attending, and having garage parking was fantastic. Definitely recommend."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (52)
"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

Prime location Historic Chicago Townhouse

9.2 out of 10, Wonderful, (65)
"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

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (18)
"I am an FCA advisor at a small rural school in Mid-Mo. We volunteer every year at the Operation Christmas Child facilities. I brought 6 high school students with me. The OCC facility is about 40 minutes from Chicago but we all wanted to experience the big city since we come from such a small rural area. The apartment was just as shown. We struggled with finding a parking spot as we drove a 10 passenger van but Dan does state that on the rental info there is no designated parking. We found...
Beautiful, Remodeled Penthouse Unit in Old Town!

Cabin 308 by 747 Lofts

9.4 out of 10, Exceptional, (14)
"Nice place, interesting neighborhood. Very convenient location!"
Cabin 308 by 747 Lofts

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

10.0 out of 10, Exceptional, (20)
"The property was beautiful and the best location in Chicago."
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, (81)
"easy communication, great place, great location. no notes! "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

50th Floor MagMile forever VIEWS, Balcony, Pool

10.0 out of 10, Exceptional, (21)
"We enjoyed everything about our stay. The amenities, cleanliness, comfort, and location were hard to beat. "
50th Floor MagMile forever VIEWS, Balcony, Pool

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

10.0 out of 10, Exceptional, (4)
"This is a very nice property in an up and coming neighborhood. The house is multilevel with three spacious bedrooms (two with ensuite bathrooms). As a bonus, the house has a garage opening onto an alleyway. Everything was very clean, bright and well appointed. The property is located in an up and coming neighborhood very convenient to good el lines and only a couple of blocks from a wonderful coffee place we used every day during our stay. Everything with the property went well and we would stay...
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

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

10.0 out of 10, Exceptional, (55)
"Excellent property, excellent location, excellent host!"
Spacious 4-Level/4-Bedroom Townhouse in West Loop

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (13)
"Everything was great. Proximity to train "L", Restuarant's near the property. "
Luxury SOHO Styled Two-Level Townhouse - Old Town

Stunning Condo #2 - Downtown River North!

9.4 out of 10, Exceptional, (16)
"This place was awesome and a great value. We had 3 coworkers stating here for a conference. Everything was great. Only semi-negative thing I could say about the place was that anything longer than a minivan will not fit in the garage."
Stunning Condo #2 - Downtown River North!

Suite + Connecting Room at a 4.5⭐️ Hotel

Suite + Connecting Room at a 4.5⭐️ Hotel

Cabin 105 by 747 Lofts

7.2 out of 10, Good, (5)
"Such a great stay ! Bed was smaller than we thought ,but had a couch that turned into a pull out bed . Close to a lot of coffee shops ,food , a couple bars . The Blue line train was also near by an easy hop on to down town . Would recommend this stay."
Cabin 105 by 747 Lofts

Cabin 202 by 747 Lofts

7.6 out of 10, Good, (5)
"OK for an overnight stay"
Cabin 202 by 747 Lofts
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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Other property types in Roosevelt Station

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (645)
"I really liked the unit and loved the amount of space the unit had"
The price is AED 403
AED 581 total
includes taxes & fees
7 Jan - 8 Jan
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (347)
"The property was very clean, it had everything we needed, the communication was excellent prior and during our stay. I will be recommending to others. "
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
8.8 out of 10, Excellent, (410)
"Beautiful Hotel with lots of amenities and entertainment in a walking distance "
The price is AED 382
AED 448 total
includes taxes & fees
30 Jan - 31 Jan
Sonder South Wabash
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.