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Far Southeast Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Far Southeast Side vacation 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, (1,374 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is CA $203
CA $239 total
includes taxes & fees
Nov 9 - Nov 10
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)
"Great stay. Clean place. Happy to come back."
United States
David F.
The price is CA $118
CA $164 total
includes taxes & fees
Oct 17 - Oct 18
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 CA $75
CA $411 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $89
CA $198 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $137
CA $337 total
includes taxes & fees
Oct 26 - Oct 27
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, (35 reviews)
"Highly recommend this property. It’s located on a quiet clean nice residential street. And the home itself is wonderful: good furnishings, comfortable, three good bedrooms, clean well appointed bathroom, great backyard. I’d stay here anytime I’m in the area."
United States
Ruth Ann G.
The price is CA $203
CA $296 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $157
CA $428 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $114
CA $143 total
includes taxes & fees
Oct 17 - Oct 18
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 CA $142
CA $357 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $144
CA $298 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $122
CA $155 total
includes taxes & fees
Oct 17 - Oct 18
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 CA $263
CA $753 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $156
CA $361 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $150
CA $512 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $105
CA $572 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $207
CA $530 total
includes taxes & fees
Oct 21 - Oct 22
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, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is CA $254
CA $373 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $198
CA $443 total
includes taxes & fees
Oct 21 - Oct 22
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A bedroom with a bed, a potted plant, a wall hanging, and a mirror.

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 CA $179
CA $619 total
includes taxes & fees
Nov 2 - Nov 3
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future stays."
Kanae 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Far Southeast Side

Everything you need to know about Far Southeast Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Far Southeast Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Far Southeast Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Far Southeast Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Far Southeast Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Far Southeast Side vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Far Southeast Side vacation rentals we have selected for you start as low as CA $239 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Far Southeast Side rentals

At Expedia, we put the best Far Southeast Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Far Southeast Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Far Southeast Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Far Southeast Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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