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Far Southeast Side Vacation Rentals

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Our top choices for Far Southeast Side vacation rentals

1. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is CA $108
CA $234 total
includes taxes & fees
Nov 23 - Nov 24
Hyde Park Trendy Studio Apartment in Good Spot

2. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (53 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is CA $166
CA $195 total
includes taxes & fees
Nov 16 - Nov 17
Wrigleyville Suites

3. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.6 out of 10, Exceptional, (14 reviews)
"Excellent communication from The Host on a beautiful property located close to everything you could want to do in Chicago. The check-in process was smooth and the host kept in constant communication to ensure that everything was Flawless from check in to check out"
United States
AJ B.
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

4. 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 CA $86
CA $274 total
includes taxes & fees
Nov 16 - Nov 17
Great Area Logan Square Apt Games Pets - Sleeps 5

5. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is CA $107
CA $372 total
includes taxes & fees
Nov 17 - Nov 18
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

6. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 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 CA $103
CA $187 total
includes taxes & fees
Dec 10 - Dec 11
Cozy studio in Andersonville Chicago

7. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (29 reviews)
"Great location! "
United States
Andrea B.
The price is CA $109
CA $244 total
includes taxes & fees
Dec 9 - Dec 10
Flexhome East Village • Modern 2BR • Quiet Street

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is CA $105
CA $279 total
includes taxes & fees
Nov 17 - Nov 18
Chic Suite/Mins to L Train /Laundry/Free Parking

9. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
The price is CA $109
CA $244 total
includes taxes & fees
Nov 24 - Nov 25
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is CA $145
CA $619 total
includes taxes & fees
Nov 30 - Dec 1
Chic Urban Retreat Near Wrigley Field w/Parking

11. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"READ THE FULL LISTING BEFORE YOU BOOK!! I've never had to jump through so many hoops to book a room before! Then they reached out multiple times via Vrbo messaging, texting and now a phone call requesting a 5 star review. What a pain just for a room to sleep in after a concert at Wrigley!With that said, the space was great! Clean, comfy and looked to have all of the essentials should you need to use the apartment more than we did."
United States
Heather B.
The price is CA $107
CA $372 total
includes taxes & fees
Nov 17 - Nov 18
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

12. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is CA $130
CA $463 total
includes taxes & fees
Nov 21 - Nov 22
Private Workspace • Sleeps 4 • Modern and Stylish

13. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (94 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is CA $217
CA $343 total
includes taxes & fees
Nov 22 - Nov 23
Kasa Lake Shore Chicago

14. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (36 reviews)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
The price is CA $118
CA $152 total
includes taxes & fees
Dec 6 - Dec 7
Beautiful Rustic Cabin for Two!

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 CA $88
CA $524 total
includes taxes & fees
Nov 16 - Nov 17
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

16. 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, (25 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 CA $150
CA $348 total
includes taxes & fees
Nov 18 - Nov 19
3BR Complete and Spacious Apartment in Ideal Spot

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

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 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 CA $102
CA $250 total
includes taxes & fees
Nov 17 - Nov 18
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

18. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (14 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is CA $90
CA $226 total
includes taxes & fees
Nov 17 - Nov 18
1BR/1BA City Comfort

19. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is CA $118
CA $447 total
includes taxes & fees
Nov 16 - Nov 17
Sleeps 7 • Huge Projector • Designated Workspace

20. 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, (37 reviews)
"Quiet neighborhood, comfy beds, attentive hosts. Would stay again."
United States
Scott n Holly K.
The price is CA $204
CA $280 total
includes taxes & fees
Nov 16 - Nov 17
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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

Find out more about Far Southeast Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Far Southeast Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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