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Far Southeast Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Far Southeast Side vacation rentals

Private kitchen

1. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is ￥12,813
￥35,303 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern bedroom with a bed, a sofa, and a hanging plant.

2. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is ￥11,376
￥23,784 total
includes taxes & fees
Nov 2 - Nov 3
Cozy studio in Andersonville Chicago
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

3. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is ￥11,136
￥48,862 total
includes taxes & fees
Oct 26 - Oct 27
Sleeps 7 • Huge Projector • Designated Workspace
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

4. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"Great stay. Clean place. Happy to come back."
United States
David F.
The price is ￥13,129
￥18,248 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Rustic Cabin for Two!
A modern living room with a blue sofa, a patterned rug, and a television.

5. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is ￥11,073
￥34,444 total
includes taxes & fees
Oct 13 - Oct 14
Great Area Logan Square Apt Games Pets - Sleeps 5
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

6. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (33 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is ￥10,862
￥28,713 total
includes taxes & fees
Oct 14 - Oct 15
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A wooden deck with a railing, a staircase, and a window with a wreath.

7. 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, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥22,610
￥32,580 total
includes taxes & fees
Oct 21 - Oct 22
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

8. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is ￥19,587
￥37,491 total
includes taxes & fees
Oct 13 - Oct 14
Chic Urban Retreat Near Wrigley Field w/Parking
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

9. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Great place to stay "
United States
Harquesha S.
The price is ￥10,707
￥28,547 total
includes taxes & fees
Oct 12 - Oct 13
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

10. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is ￥12,104
￥31,226 total
includes taxes & fees
Oct 12 - Oct 13
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Private kitchen

11. 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 traveler
The price is ￥29,263
￥83,150 total
includes taxes & fees
Oct 13 - Oct 14
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (81 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is ￥18,770
￥48,801 total
includes taxes & fees
Oct 21 - Oct 22
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

13. 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, (71 reviews)
"Easy access to the Green Line."
United States
Michael
The price is ￥16,748
￥38,166 total
includes taxes & fees
Nov 4 - Nov 5
Chic Suite/Mins to L Train /Laundry/Free Parking
A modern building with the name 'SENIORAL' prominently displayed on the facade.

14. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,361 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥28,978
￥34,017 total
includes taxes & fees
Oct 26 - Oct 27
Sentral Michigan Avenue
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

15. 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 ￥16,274
￥38,159 total
includes taxes & fees
Nov 2 - Nov 3
2BR Apt with 2 Baths & Laundry
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

16. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is ￥23,252
￥49,301 total
includes taxes & fees
Oct 15 - Oct 16
3BR Complete and Spacious Apartment in Ideal Spot
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

17. 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 ￥12,743
￥16,068 total
includes taxes & fees
Oct 11 - Oct 12
King Bed | Non-Smoking
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

18. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥17,210
￥37,267 total
includes taxes & fees
Oct 28 - Oct 29
The Oak Park Loft
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.

19. 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 ￥21,993
￥77,127 total
includes taxes & fees
Oct 19 - Oct 20
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Lake

20. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (57 reviews)
"Location is perfect"
United States
Mary
The price is ￥28,314
￥43,064 total
includes taxes & fees
Nov 5 - Nov 6
Kasa Lake Shore Chicago
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Great stay, comfy beds :)"
Cindy 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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