A man standing on a rocky outcrop with a large concrete structure in the background.

Far Southeast Side Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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
9.2 out of 10, Wonderful, (1,273 reviews)
"Nice stay"
United States
Heather
$176 nightly
The price is $207
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
8.2 out of 10, Very Good, (17 reviews)
"Great location and super clean!"
United States
Erica
$217 nightly
The price is $258
Sep 9 - Sep 10
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
$289 nightly
The price is $339
Aug 31 - Sep 1
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, (31 reviews)
"I had a fun stay "
United States
Jusu K.
$178 nightly
The price is $199
Aug 24 - Aug 25
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

5. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$229 nightly
The price is $271
Aug 23 - Aug 24
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR

6. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
Cozy Studio Suite, Steps from River North & Shops
A kitchen with white cabinets, a microwave, a kettle, and a toaster.

7. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
$1,172 nightly
The price is $1,386
Aug 22 - Aug 23
Total with taxes and fees
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

8. 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
$214 nightly
The price is $253
Aug 23 - Aug 24
Total with taxes and fees
LIVN West Loop Chicago King Studio
A modern building with a glass facade, surrounded by a parking area and greenery.

9. Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (30 reviews)
"An incredible experience and wonderful place to stay. A perfect location, quiet, and my twin boys loved having their own spaces. Thank you so much!"
United States
Miriam B.
$372 nightly
The price is $459
Aug 31 - Sep 1
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views

10. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, and stylish!"
United States
Maurya K.
$472 nightly
The price is $582
Sep 2 - Sep 3
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
A modern kitchen with a central island, bar stools, and a dining table.

11. 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, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
$1,520 nightly
The price is $1,823
Sep 6 - Sep 7
Total with taxes and fees
River North Private Deck With In and Out Parking
A living room with a blue sectional sofa, a glass coffee table, and yellow curtains.

12. 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.
$238 nightly
The price is $255
Sep 8 - Sep 9
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

13. South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
$540 nightly
The price is $620
Sep 3 - Sep 4
Total with taxes and fees
South Loop Rooftop With In and Out Parking 2
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

14. 3BR | Complete & Well-Located Apt in Hyde Park

3BR | Complete & Well-Located Apt in Hyde Park
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Enjoyed our stay. Thank you"
United States
Nicolle C.
$214 nightly
The price is $235
Aug 24 - Aug 25
Total with taxes and fees
3BR | Complete & Well-Located Apt in Hyde Park
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

15. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (9 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
$442 nightly
The price is $499
Sep 8 - Sep 9
Total with taxes and fees
River North Rooftop With In and Out Parking 3
A modern living room with a blue sofa, a leather armchair, and a geometric coffee table.

16. LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (8 reviews)
"We loved the location."
United States
Nicoll M.
$500 nightly
The price is $591
Aug 26 - Aug 27
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 2 BR
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a gas stove.

17. Charming & Cozy Getaway - A Heroic Stay Awaits!

Charming & Cozy Getaway - A Heroic Stay Awaits!
Homewood
10.0 out of 10, Exceptional, (20 reviews)
"We had such a lovely stay. It was cute, quaint, and the perfect place to spend Mother’s Day with my mother. The space was cozy, clean, and had such a peaceful charm to it. We truly enjoyed our time here and would absolutely stay again!"
United States
Nikki B.
$370 nightly
The price is $411
Sep 8 - Sep 9
Total with taxes and fees
Charming & Cozy Getaway - A Heroic Stay Awaits!
A room with a large window, a round table with chairs, a television, and a lamp.

18. 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.
$188 nightly
The price is $222
Aug 23 - Aug 24
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
A modern living room with a sofa, coffee table, and dining area. Large windows offer views of the cityscape.

19. 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.
$587 nightly
The price is $654
Sep 1 - Sep 2
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.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (78 reviews)
"Excellent place to stay!"
United States
Alicia K.
$294 nightly
The price is $336
Aug 24 - Aug 25
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Far Southeast Side Hotel Reviews

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"It was our first time in Chicago and this hotel is at the best location. Walking distance to so many places and restaurants. The room was very spacious and clean. I would definitely stay here again"
Bobby 2-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

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 $151 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.

Explore a world of travel with Expedia