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Far Southeast Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Far Southeast Side vacation rentals

A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

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 $102
CA $225 total
includes taxes & fees
Nov 16 - Nov 17
Hyde Park Trendy Studio Apartment in Good Spot
A modern living room with a sofa, coffee table, and TV. There are windows with blinds, a radiator, and a plant.

2. Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Great place, great location!"
United States
Lisa T.
The price is CA $121
CA $283 total
includes taxes & fees
Nov 11 - Nov 12
Sleek & Functional 2-Bedroom Apt
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,413 reviews)
"Great for extended stays."
United States
Jeff
The price is CA $263
CA $309 total
includes taxes & fees
Nov 12 - Nov 13
Sentral Michigan Avenue
A rooftop terrace with a brick wall, large windows, and a metal railing.

4. 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 $175
CA $437 total
includes taxes & fees
Nov 14 - Nov 15
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.

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 $106
CA $367 total
includes taxes & fees
Nov 11 - Nov 12
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

6. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (88 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is CA $215
CA $339 total
includes taxes & fees
Nov 22 - Nov 23
Kasa Lake Shore Chicago
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, (83 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is CA $152
CA $398 total
includes taxes & fees
Nov 11 - Nov 12
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.

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 $122
CA $298 total
includes taxes & fees
Nov 17 - Nov 18
Chic Suite/Mins to L Train /Laundry/Free Parking
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

9. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
The price is CA $71
CA $383 total
includes taxes & fees
Nov 17 - Nov 18
Studio Near Wrigley • Sleeps 4 • Games • Fireplace
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

10. 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 $101
CA $247 total
includes taxes & fees
Nov 16 - Nov 17
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A modern living room with a sofa, a TV, and a dining area with stools.

11. 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 $102
CA $281 total
includes taxes & fees
Nov 11 - Nov 12
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

12. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (49 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 11 - Nov 12
Wrigleyville Suites
A modern bedroom with a bed, a sofa, and a hanging plant.

13. 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 $102
CA $185 total
includes taxes & fees
Dec 10 - Dec 11
Cozy studio in Andersonville Chicago
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

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 $117
CA $150 total
includes taxes & fees
Dec 6 - Dec 7
Beautiful Rustic Cabin for Two!
Private kitchen

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

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (6 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveller
The price is CA $261
CA $819 total
includes taxes & fees
Nov 15 - Nov 16
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

16. 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 $608 total
includes taxes & fees
Nov 11 - Nov 12
Chic Urban Retreat Near Wrigley Field w/Parking
A living room with a flat-screen TV on a wooden cabinet, a dark sofa, a coffee table, a floor lamp, and a potted plant.

17. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (13 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is CA $89
CA $224 total
includes taxes & fees
Nov 16 - Nov 17
1BR/1BA City Comfort
A wooden deck with a railing, a staircase, and a window with a wreath.

18. 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 $202
CA $277 total
includes taxes & fees
Nov 12 - Nov 13
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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 CA $87
CA $515 total
includes taxes & fees
Nov 11 - Nov 12
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A modern building with a brick facade, large windows, and a central entrance area.

20. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is CA $126
CA $311 total
includes taxes & fees
Nov 17 - Nov 18
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Love the location and the nostalgic look"
Valerie 3-night trip
Posted less than an hour ago
Congress Plaza Hotel

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 $195 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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