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Far Southeast Side Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (1,301 reviews)
"A great place"
United States
Lahiru
$175 nightly
The price is $205
Sep 7 - Sep 8
Total with taxes and fees
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (25 reviews)
"Great location and super clean!"
United States
Erica
$227 nightly
The price is $270
Sep 7 - Sep 8
Total with taxes and fees
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
$330 nightly
The price is $387
Sep 7 - Sep 8
Total with taxes and fees
Level Chicago – Old Town
A wooden deck with a railing, a staircase, and a window with a wreath.

4. 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, (34 reviews)
"I had a fun stay "
United States
Jusu K.
$184 nightly
The price is $206
Sep 7 - Sep 8
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

5. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
$189 nightly
The price is $223
Sep 7 - Sep 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

6. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
$208 nightly
The price is $246
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
A living room with a blue sectional sofa, a glass coffee table, and yellow curtains.

7. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.2 out of 10, Wonderful, (11 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
$244 nightly
The price is $261
Sep 29 - Sep 30
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

8. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
$306 nightly
The price is $343
Sep 7 - Sep 8
Total with taxes and fees
River North Private Balcony With In and Out Parking
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

9. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
$224 nightly
The price is $251
Sep 7 - Sep 8
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
A modern living room with a sofa, coffee table, and dining area. Large windows offer views of the cityscape.

10. Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.0 out of 10, Wonderful, (4 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
$566 nightly
The price is $628
Sep 20 - Sep 21
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 1
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (79 reviews)
"Excellent place to stay!"
United States
Alicia K.
$274 nightly
The price is $314
Sep 14 - Sep 15
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern kitchen with a central island, bar stools, and a dining table.

12. River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (14 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
$556 nightly
The price is $633
Sep 29 - Sep 30
Total with taxes and fees
River North Private Deck With In and Out Parking
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

13. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
$201 nightly
The price is $237
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago King Studio
A modern hotel room with a large bed, a small dining table, a bench, and a view of the city through a large window.

14. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
$176 nightly
The price is $208
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

15. Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Spacious, free parking, family friendly"
United States
Majid
$543 nightly
The price is $617
Sep 21 - Sep 22
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 1
A room with a large window, a round table with chairs, a television, and a lamp.

16. LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
$208 nightly
The price is $246
Sep 7 - Sep 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

17. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (32 reviews)
"Great stay. Clean place. Happy to come back."
United States
David F.
$103 nightly
The price is $115
Sep 7 - Sep 8
Total with taxes and fees
Beautiful Rustic Cabin for Two!
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

18. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.2 out of 10, Wonderful, (10 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
$189 nightly
The price is $223
Sep 7 - Sep 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Studio
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

19. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
$812 nightly
The price is $1,002
Sep 16 - Sep 17
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments
A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

20. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
$185 nightly
The price is $197
Sep 9 - Sep 10
Total with taxes and fees
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
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
"Absolutely amazing place to stay amazing. Customer service shout out to all the dudes at the front desk."
Jaden 2-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 $205 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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