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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 modern kitchen with a stainless steel stove, double sink, and white cabinetry.

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
$148 nightly
The price is $164
Nov 23 - Nov 24
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

2. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (52 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
$119 nightly
The price is $139
Nov 16 - Nov 17
Total with taxes and fees
Wrigleyville Suites
Game room

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
A row of residential houses with a wooden fence in the foreground.

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.
$173 nightly
The price is $193
Nov 16 - Nov 17
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A beach with a sandy shore and calm sea.

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.
$217 nightly
The price is $261
Nov 17 - Nov 18
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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.
$106 nightly
The price is $131
Dec 10 - Dec 11
Total with taxes and fees
Cozy studio in Andersonville Chicago
A two-story brick building with a white door open to a wooden interior.

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.
$139 nightly
The price is $171
Dec 9 - Dec 10
Total with taxes and fees
Flexhome East Village • Modern 2BR • Quiet Street
A dining table set with plates, glasses, and a vase of flowers.

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
$168 nightly
The price is $192
Nov 17 - Nov 18
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

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.
$139 nightly
The price is $171
Nov 15 - Nov 16
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A building with a brick facade and a large glass window. There is a staircase with a black railing leading to the entrance.

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
$418 nightly
The price is $430
Nov 29 - Nov 30
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A beach with a sandy shore and calm sea.

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.
$217 nightly
The price is $261
Nov 17 - Nov 18
Total with taxes and fees
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

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.
$275 nightly
The price is $324
Nov 21 - Nov 22
Total with taxes and fees
Private Workspace • Sleeps 4 • Modern and Stylish
A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

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
$202 nightly
The price is $240
Nov 22 - Nov 23
Total with taxes and fees
Kasa Lake Shore 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.
$95 nightly
The price is $106
Dec 6 - Dec 7
Total with taxes and fees
Beautiful Rustic Cabin for Two!
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
$294 nightly
The price is $363
Nov 15 - Nov 16
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A modern kitchen with white cabinets, stainless steel appliances, and a bar area with stools.

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
$222 nightly
The price is $244
Nov 18 - Nov 19
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
A living room with a brick fireplace, leather sofa, and a ceiling fan.

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.
$165 nightly
The price is $176
Nov 17 - Nov 18
Total with taxes and fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A wooden console table with a black metal frame, a clock, two bottles, and a decorative sphere on the shelf.

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.
$145 nightly
The price is $159
Nov 17 - Nov 18
Total with taxes and fees
1BR/1BA City Comfort
A hotel room with a large bed, a window with blinds, a projector screen displaying a castle, and a neatly made bed with towels.

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.
$264 nightly
The price is $312
Nov 16 - Nov 17
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
A wooden deck with a railing, a staircase, and a window with a wreath.

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.
$176 nightly
The price is $197
Nov 16 - Nov 17
Total with taxes and fees
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

River Hotel

River Hotel

10/10 Excellent
"We had a wonderful experience at the River Hotel in Chicago, but what impressed me most was the exceptional customer service and flexibility we received when our travel plans unexpectedly changed. Due to circumstances entirely outside the hotel’s control, we needed to make adjustments to our reservation. The staff were incredibly understanding, accommodating, and reasonable in helping us navigate the situation. What stood out most was that they went above and beyond to assist us, even though they were under no obligation to do so. It’s easy to provide good hospitality when everything goes according to plan, but I believe the true measure of customer service is how a business responds when things don’t. The River Hotel demonstrated genuine consideration for its guests rather than simply relying on policies and technicalities. We sincerely appreciated their kindness and professionalism. This experience has certainly earned our loyalty, and we would happily stay here again on future visits to Chicago. Highly recommended!"
Benjamin 4-night trip
Posted 1 hour ago
River 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Far Southeast Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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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