Photo by Marc Jacobs

Far Southeast Side Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

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

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

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

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Far Southeast Side

A Home Away From Home!

9.6 out of 10, Exceptional, (11)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (944)
"Near everything great amenities "
$220 nightly
The price is $258
Oct 5 - Oct 6
Total with taxes and fees
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (539)
"Very great place to stay!"
$200 nightly
The price is $235
Oct 6 - Oct 7
Total with taxes and fees
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (360)
"Great place to stay. Loved it!"
$278 nightly
The price is $327
Oct 19 - Oct 20
Total with taxes and fees
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (372)
"Great stay!"
$129 nightly
The price is $151
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (235)
"Great location and lovely amenities. "
$159 nightly
The price is $187
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (355)
"nice area, shops nearby"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (670)
"great room, clean good space and close to places "
$139 nightly
The price is $163
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (206)
"This place was perfect "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (52)
"Place was in a great location close to good restaurants "
$139 nightly
The price is $163
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
$291 nightly
The price is $342
Oct 5 - Oct 6
Total with taxes and fees
Kasa River North Chicago

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
$131 nightly
The price is $145
Oct 2 - Oct 3
Total with taxes and fees
Wrigleyville Suites

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (180)
"Great location!!!"
$186 nightly
The price is $219
Oct 22 - Oct 23
Total with taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (62)
"Good "
$79 nightly
The price is $89
Oct 5 - Oct 6
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Stylish Apartment near Chicago Downtown

2.0 star property
$214 nightly
The price is $252
Oct 2 - Oct 3
Total with taxes and fees
Stylish Apartment near Chicago Downtown

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.6 out of 10, Good, (139)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (25)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
$169 nightly
The price is $187
Oct 2 - Oct 3
Total with taxes and fees
Clean & Equipped 1BR Apt

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (19)
"This place was great! Loved my stay!"
$193 nightly
The price is $213
Oct 2 - Oct 3
Total with taxes and fees
Charming 2BR in Vibrant Lakeview

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
$192 nightly
The price is $214
Oct 15 - Oct 16
Total with taxes and fees
Stylish 1BR in West Loop
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Far Southeast Side Hotel Reviews

Find out more about Far Southeast Side

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 $89 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.