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Far Southeast Side Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Far Southeast Side holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,377 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,124
HK$1,319 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

2. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
The price is HK$651
HK$905 total
includes taxes & fees
25 Oct - 26 Oct
Beautiful Rustic Cabin for Two!
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

3. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
The price is HK$380
HK$2,221 total
includes taxes & fees
2 Nov - 3 Nov
Private Workspace • Sleeps4 • Modern Stylish Stay
A modern bedroom with a bed, a sofa, and a hanging plant.

4. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (104 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is HK$494
HK$1,094 total
includes taxes & fees
2 Nov - 3 Nov
Cozy studio in Andersonville Chicago
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

5. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is HK$720
HK$1,822 total
includes taxes & fees
2 Nov - 3 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A wooden deck with a railing, a staircase, and a window with a wreath.

6. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (36 reviews)
"I had a fun stay "
United States
Jusu K.
The price is HK$1,123
HK$1,636 total
includes taxes & fees
21 Oct - 22 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

7. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is HK$848
HK$2,327 total
includes taxes & fees
26 Oct - 27 Oct
Cozy, Comfortable and Convenient apartment. Close to everything!
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

8. King Bed | Non-Smoking

King Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (68 reviews)
"The place is not clean and it smells really bad. It did not look anything like the pictures."
United States
Luis
The price is HK$631
HK$796 total
includes taxes & fees
20 Oct - 21 Oct
King Bed | Non-Smoking
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

9. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is HK$824
HK$2,021 total
includes taxes & fees
20 Oct - 21 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
United States
Bridget
The price is HK$805
HK$1,656 total
includes taxes & fees
3 Nov - 4 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

11. Premium King Bed|Portage

Premium King Bed|Portage
Portage
10.0 out of 10, Exceptional, (65 reviews)
"Sketchy property location, not clearly marked on the street (kind of hard to find), unnecessary poor communication regarding check-in procedures, (just like a regular front desk experience but they make it complicated) The room was ok, bed was fine, staff was very helpful, property condition was just ok."
United States
Dave
The price is HK$679
HK$859 total
includes taxes & fees
20 Oct - 21 Oct
Premium King Bed|Portage
Private kitchen

12. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (5 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveller
The price is HK$1,452
HK$4,126 total
includes taxes & fees
20 Oct - 21 Oct
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

13. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is HK$1,075
HK$2,276 total
includes taxes & fees
26 Oct - 27 Oct
2BR Apt with 2 Baths & Laundry
A modern living room with a white coffee table, a vase with flowers, a bottle of wine, and a cheese board with snacks.

14. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
9.4 out of 10, Exceptional, (8 reviews)
"Great property in a central location. Neighborhood was quiet and safe with good parks nearby. Apartment had good amenities and perfect for our stay. Communication with host was excellent"
United States
Carey M.
The price is HK$670
HK$2,611 total
includes taxes & fees
28 Oct - 29 Oct
2BR Fitness Pad • Private Gym • Sleeps 7
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

15. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is HK$553
HK$3,103 total
includes taxes & fees
20 Oct - 21 Oct
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A rooftop terrace with a brick wall, large windows, and a metal railing.

16. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is HK$565
HK$2,117 total
includes taxes & fees
21 Oct - 22 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Lake

17. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (72 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is HK$1,405
HK$2,063 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A hotel room with a bed, a view of a cityscape, and a window with curtains.

18. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is HK$1,168
HK$2,517 total
includes taxes & fees
22 Oct - 23 Oct
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A playground with a climbing structure and a fenced area, a parked car, and trees.

19. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (4 reviews)
"I had an amazing stay at Tracee's place. It was quiet, clean, plenty of parking and served all of my needs. Tracee was responsive and very accommodating of my stay."
United States
Denise R.
The price is HK$932
HK$3,339 total
includes taxes & fees
26 Oct - 27 Oct
Zen City Escape | Patio + Free Parking
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 Far Southeast Side Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"The room size was big enough for me. I had a good view of the river and downtown. The staff was helpful. There was no restaurant in the building, but it was one on each side of the hotel."
Isaac Lee 3-night trip
Posted less than an hour ago
River Hotel

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