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Our top choices for Far Southwest Side vacation rentals
1. Sentral Michigan Avenue
Sentral Michigan Avenue4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,415 reviews)
9.0/10
Wonderful
(1,415 reviews)
"Great for extended stays."
"Great for extended stays."
Jeff
The price is NT$6,284
NT$6,284
NT$7,377 total
includes taxes & fees
Dec 6 - Dec 7
2. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (90 reviews)
8.8/10
Excellent
(90 reviews)
"The bathroom was really clean. The beds were really comfortable"
"The bathroom was really clean. The beds were really comfortable"Jair
The price is NT$4,995
NT$4,995
NT$7,582 total
includes taxes & fees
Nov 26 - Nov 27
3. Level Chicago – Old Town
Level Chicago – Old Town4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (562 reviews)
9.2/10
Wonderful
(562 reviews)
"Super clean and friendly staff! Would definitely stay here again"
"Super clean and friendly staff! Would definitely stay here again"Robert Edward
The price is NT$5,619
NT$5,619
NT$7,407 total
includes taxes & fees
Nov 22 - Nov 23
4. At Home in Oak Park
At Home in Oak Park3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
9.6/10
Exceptional
(14 reviews)
"Great location with parking included"
"Great location with parking included"Melissa
5. Wrigleyville Suites
Wrigleyville Suites2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
9.6/10
Exceptional
(51 reviews)
"The area was nice! Many restaurants and stores are at walking distance
Room was very nice and clean"
"The area was nice! Many restaurants and stores are at walking distance
Room was very nice and clean"Francisco
The price is NT$3,905
NT$3,905
NT$4,584 total
includes taxes & fees
Nov 30 - Dec 1
6. Historic Oak Park Home
Historic Oak Park Home2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
8.8/10
Excellent
(6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."Janette
The price is NT$7,039
NT$7,039
NT$11,707 total
includes taxes & fees
Nov 19 - Nov 20
7. Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue Line3.0 star property
Forest Park
The price is NT$7,953
NT$7,953
NT$15,604 total
includes taxes & fees
Nov 17 - Nov 18
8. Historic Oak Park Residence
Historic Oak Park Residence2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
9.6/10
Exceptional
(12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"Ann-Marie
9. The Oak Park Loft
The Oak Park Loft2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
9.4/10
Exceptional
(8 reviews)
"Good location, nice neighborhood, restaurants close"
"Good location, nice neighborhood, restaurants close"Linda
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.
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.
Find vacation rentals that suit your style
Top Far Southwest Side Hotel Reviews
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago
10/10 Excellent
Beautiful views and great staff to accommodate any needs
Beautiful views and great staff to accommodate any needs
Griffin
SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago LombardHighland Hills
10/10 Excellent
No complaints
No complaints
Margaret
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoDowntown Chicago
10/10 Excellent
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
Jennifer
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopDowntown Chicago
10/10 Excellent
Nice hotel, fair warning they take a $225 security deposit on top of the total for the room. This was not mentioned anywhere on the properties page and Expedia needs to add this detail.
Nice hotel, fair warning they take a $225 security deposit on top of the total for the room. This was not mentioned anywhere on the properties page and Expedia needs to add this detail.
Jason
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South LoopDowntown Chicago
10/10 Excellent
Perfect location, walked to Soldier Field for a concert, walked to museums. Hopped on the train around the corner to go North. All hotel employees were so friendly and helpful, would definitely stay again!
Perfect location, walked to Soldier Field for a concert, walked to museums. Hopped on the train around the corner to go North. All hotel employees were so friendly and helpful, would definitely stay again!
Abra
Le Méridien Essex Chicago
Le Méridien Essex ChicagoDowntown Chicago
10/10 Excellent
Extremely easy check in, attentive and friendly staff, the attached restaurant and staff where great, we where given a credit to use at the restaurant upon check in at the hotel. The rooms are a bit small, but will do if your single or a couple, we feel the like shower design could be better as it causes water to get on the floor, the downside is parking, but it’s the cost of being in a prime location, I would stay again
Extremely easy check in, attentive and friendly staff, the attached restaurant and staff where great, we where given a credit to use at the restaurant upon check in at the hotel. The rooms are a bit small, but will do if your single or a couple, we feel the like shower design could be better as it causes water to get on the floor, the downside is parking, but it’s the cost of being in a prime location, I would stay again
Shamara
ACME Hotel Chicago, Outset Collection by Hilton
ACME Hotel Chicago, Outset Collection by HiltonDowntown Chicago
10/10 Excellent
Three day trip to Chicago. The hotel was a great central location in downtown and a 10 to 15 minute walk to most sites, Navy Pier, River walk, Michigan Avenue, all the great pizza places. The hotel was smaller compared to most which we loved. Room was updated, bathroom very nice and king sized bed very comfortable. We used the blue line to get to and from O’Hare via Clark station (a 12 minute walk from hotel.). We used the red line via Chicago station (10 min walk from hotel) to go see a Cubs...
Three day trip to Chicago. The hotel was a great central location in downtown and a 10 to 15 minute walk to most sites, Navy Pier, River walk, Michigan Avenue, all the great pizza places. The hotel was smaller compared to most which we loved. Room was updated, bathroom very nice and king sized bed very comfortable. We used the blue line to get to and from O’Hare via Clark station (a 12 minute walk from hotel.). We used the red line via Chicago station (10 min walk from hotel) to go see a Cubs...
Claudia
Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton MarketDowntown Chicago
10/10 Excellent
The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...
The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...
Valia
Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent MileDowntown Chicago
10/10 Excellent
Clean room, friendly and hospitable staff, great location!
Clean room, friendly and hospitable staff, great location!
Katie
Best Western Grant Park Hotel
Best Western Grant Park HotelDowntown Chicago
10/10 Excellent
Great location. Easy check in and check out process. Room was clean and comfty. Awesome eating and transportation options nearby.
Great location. Easy check in and check out process. Room was clean and comfty. Awesome eating and transportation options nearby.
brian
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesDowntown Chicago
10/10 Excellent
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two...
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two...
Joanna
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileDowntown Chicago
10/10 Excellent
The hotel was great. I was placed in a room. Where constructoon was going on outside. I had planned to sleep in, but at 715 the sound of a jack hanmer woke me up.
The hotel was great. I was placed in a room. Where constructoon was going on outside. I had planned to sleep in, but at 715 the sound of a jack hanmer woke me up.
Rudy
Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by HiltonDowntown Chicago
10/10 Excellent
This lovely hotel is nestled in a neighborhood that is quiet and very upscale. There are several restaurants in the area as well as a bar and restaurant (serving limited light fare) in the hotel lobby. For our purposes, it was located and very walkable.
Our room was spacious and very well appointed. We stayed in a deluxe king room that offered a sitting area as well as a sleeping area. The decor was understated but elegant and comfortable. the bathroom featured a walk in shower which we prefer...
This lovely hotel is nestled in a neighborhood that is quiet and very upscale. There are several restaurants in the area as well as a bar and restaurant (serving limited light fare) in the hotel lobby. For our purposes, it was located and very walkable.
Our room was spacious and very well appointed. We stayed in a deluxe king room that offered a sitting area as well as a sleeping area. The decor was understated but elegant and comfortable. the bathroom featured a walk in shower which we prefer...
jolynn
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago DowntownDowntown Chicago
10/10 Excellent
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
Shatani
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
10/10 Excellent
Great location
Great location
blerina
L7 CHICAGO by LOTTE HOTELS
L7 CHICAGO by LOTTE HOTELSDowntown Chicago
10/10 Excellent
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
Erin
citizenM Chicago Downtown
citizenM Chicago DowntownDowntown Chicago
10/10 Excellent
Great location, clean room and friendly staff!
Great location, clean room and friendly staff!
Diani
LIVN - West Loop Chicago
LIVN - West Loop ChicagoDowntown Chicago
10/10 Excellent
NA
NA
Santhi
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent MileDowntown Chicago
10/10 Excellent
Everything was perfect and the customer service was awesome
Everything was perfect and the customer service was awesome
Elsie
Hotel 505 River North
Hotel 505 River NorthDowntown Chicago
10/10 Excellent
Across from Nordstroms! Staff helpfu!
Across from Nordstroms! Staff helpfu!
shanea
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Vacation Apartments in Far Southwest Side
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