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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (86)
"Location of house is great, communication with owner is great. The house "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Exterior

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

9.6 out of 10, Exceptional, (8)
"The house is located in a neighborhood that is easily walkable and has anything you need within walking distance. Metro is located within a few blocks of the house and makes getting around easy."
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Luxury House in the heart of Old Town with Parking
Smart TV, fireplace, video games, foosball

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (44)
"Fantastic house…whole family enjoyed our stay. Thank you!"
Luxury House in the heart of Old Town with Parking
Cabin 308 by 747 Lofts
Exterior

Cabin 308 by 747 Lofts

9.4 out of 10, Exceptional, (14)
"Nice place, interesting neighborhood. Very convenient location!"
The price is AED 208
AED 528 total
includes taxes & fees
9 Mar - 10 Mar
Cabin 308 by 747 Lofts
Stunning Condo #2 - Downtown River North!
Fridge, microwave, oven, stovetop

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!
Top 1 Rated 4BR Lincoln Park House - King Bed
Interior

Top 1 Rated 4BR Lincoln Park House - King Bed

2.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was as it was described. Very nice "
The price is AED 309
AED 2,039 total
includes taxes & fees
5 Mar - 6 Mar
Top 1 Rated 4BR Lincoln Park House - King Bed
ART Downtn RoofDeck-Private Grg-3 bdrm HOME-EVTesla -Sleeps 10-Pets
Miscellaneous

ART Downtn RoofDeck-Private Grg-3 bdrm HOME-EVTesla -Sleeps 10-Pets

10.0 out of 10, Exceptional, (1)
"My family and I had a wonderful weekend in Chicago, all thanks to your beautiful home. We comfortably slept four people and enjoyed the ample space. The house is filled with stunning natural light during the day, thanks to the full windows on the second floor and a skylight in the stairwell leading to the third floor. One of the features we loved the most was the parking and the use of the garage. The kitchen was easy to navigate, and we appreciated the selection of coffee available."
ART Downtn RoofDeck-Private Grg-3 bdrm HOME-EVTesla -Sleeps 10-Pets
Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom
Private kitchen

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
Beautiful, Remodeled Penthouse Unit in Old Town!
Fridge, microwave, oven, stovetop

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (19)
"Fantastic location, large apartment and communication was excellent. Perfect for a large group! "
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Terrace/patio

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

10.0 out of 10, Exceptional, (20)
"We celebrated Christmas in this stunning home with our adult children and spouses. We had 10 adults and this house was perfect! So big and comfortable and we used every inch. The bedrooms are all large and comfortable with bathrooms which gave everyone privacy and very convenient when we were all getting ready at the same time. The house was well stocked with everything you could imagine. Check in was a breeze and the manager was just a text away if we had any questions. Our best...
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Prime location Historic Chicago Townhouse
TV, fireplace, books, offices

Prime location Historic Chicago Townhouse

9.4 out of 10, Exceptional, (66)
"Beautiful old Gold Coast Townhouse within walking distance of everything we needed. Spacious accommodations with a lovely large dining area and comfortable TV lounging area at back of house. Close to plenty of dining options and Lake Michigan. Fully stocked kitchen, comfortable beds and bedding. Plenty of towels, coffee and tea. Comfy robes in every bedroom. Overall a wonderful experience."
Prime location Historic Chicago Townhouse
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Fridge, microwave, oven, stovetop

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
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Full-size fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (83)
"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
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Terrace/patio

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
50th Floor MagMile forever VIEWS, Balcony, Pool
Pool

50th Floor MagMile forever VIEWS, Balcony, Pool

10.0 out of 10, Exceptional, (21)
"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
Spacious 4-Level/4-Bedroom Townhouse in West Loop
Point of interest

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
Terrace/patio

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (13)
"Awesome location for restaurants, bars, and comedy shows. Close proximity to everything. Spent a long weekend here and had no problem getting to and from ORD, Soldier Field, and Wrigleyville. Property was exactly as expected. Comfy beds. Clean and easy to check in. "
Luxury SOHO Styled Two-Level Townhouse - Old Town
2 Connecting Suites at a 4⭐️ Hotel
Beach

2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 4⭐️ Hotel
Best Location/ Designer themed/ Patio/ Queen beds/ Parking
Fridge, microwave, oven, stovetop

Best Location/ Designer themed/ Patio/ Queen beds/ Parking

2.0 star property
10.0 out of 10, Exceptional, (2)
"The accommodations was 5 star. Just as described and accommodated my family for the shortb stay. The owner met us and was gracious"
Best Location/ Designer themed/ Patio/ Queen beds/ Parking
Level River North - Junior 2 Bedroom Suite
Pool

Level River North - Junior 2 Bedroom Suite

Level River North - Junior 2 Bedroom Suite
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (690)
"it was alright, $77 extra for parking, no breakfast included but it was like a little apartment. no fan for guests either. no phone for communication but u can text their number yet they take forever to respond. "
The price is AED 465
AED 654 total
includes taxes & fees
9 Mar - 10 Mar
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (442)
"Loved the app and process for checking-in and out. The property itself could use some TLC, there were lots of scuff marks and scratches in the walls due to prior tenants. Our unit could have used a painting. There also wasn't a space to get extra toiletries per the app, would take this out if it's not really an option. "
The price is AED 336
AED 394 total
includes taxes & fees
27 Mar - 28 Mar
Sonder South Wabash
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AED 493
AED 578 total
includes taxes & fees
5 Mar - 6 Mar
Found Chicago powered by Sonder
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.