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Far Southeast Side Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Far Southeast Side vacation rentals

Lake

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
$298 nightly
The price is $355
Aug 9 - Aug 10
Total with taxes and fees
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,208 reviews)
$208 nightly
The price is $244
Aug 9 - Aug 10
Total with taxes and fees
Sentral Michigan Avenue
Living area

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
$110 nightly
The price is $126
Jul 22 - Jul 23
Total with taxes and fees
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
$239 nightly
The price is $282
Jul 12 - Jul 13
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
TV, offices

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.
$286 nightly
The price is $338
Jul 16 - Jul 17
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"My group and I traveled to town this weekend for a music festival and had the opportunity to stay at this place and had a great time. Communication with the host was very prompt when we had any questions which I appreciate a lot. Also, the place was clean and spacious for our group and easy to come in and out. Would recommend this place to others looking for a place to stay in town."
United States
Marcos B.
$321 nightly
The price is $396
Jul 16 - Jul 17
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (500 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$371 nightly
The price is $436
Aug 9 - Aug 10
Total with taxes and fees
Level Chicago – Old Town
Terrace/patio

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, (57 reviews)
"So hospitable "
United States
Adrian
$375 nightly
The price is $451
Jul 16 - Jul 17
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
1 bedroom, desk, iron/ironing board, WiFi

Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (84 reviews)
"Wonderful hosts…very kind and communicative. Awesome area… highly recommended!"
United States
Andrew C.
$154 nightly
The price is $189
Jul 27 - Jul 28
Total with taxes and fees
Cozy studio in Andersonville Chicago
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (816 reviews)
"Great place to stay."
United States
Benedictine
$307 nightly
The price is $360
Jul 19 - Jul 20
Total with taxes and fees
Kasa Magnificent Mile Chicago
Interior

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, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
Premium Urban 4BR - Perfect Mix of Comfort & Location
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$525 nightly
The price is $601
Jul 19 - Jul 20
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Interior

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$228 nightly
The price is $270
Jul 13 - Jul 14
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
Interior

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (30 reviews)
"Easy to find little cabin in Griffith"
United States
Allison R.
$110 nightly
The price is $123
Jul 22 - Jul 23
Total with taxes and fees
Beautiful Rustic Cabin for Two!
Smart TV, video games

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.
$242 nightly
The price is $271
Aug 5 - Aug 6
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (85 reviews)
"Great place to stay. Within walking distance to breweries and restaurants. "
United States
Carrie K.
$296 nightly
The price is $365
Jul 13 - Jul 14
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$276 nightly
The price is $316
Jul 13 - Jul 14
Total with taxes and fees
The Oak Park Loft
Smart TV, books

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, (65 reviews)
"This was a very cute apartment in a really nice neighborhood! We got a little confused about check-in because the parking space and the lockbox are not clearly marked. A couple of big, comfy couches in the living room would have made it a little more comfortable for 2 adults and 2 tall teenagers. Otherwise it was perfect and we would definitely stay again."
United States
Erin
$237 nightly
The price is $271
Jul 28 - Jul 29
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
Smart TV

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.6 out of 10, Exceptional, (17 reviews)
"Great place to stay "
United States
Harquesha S.
$169 nightly
The price is $180
Jul 12 - Jul 13
Total with taxes and fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
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

Omni Chicago Hotel

Omni Chicago Hotel

10/10 Excellent
"This was our first Omni hotel stay and I kept thinking the entire time that I would now be Omni loyal moving forward. The staff really made it. We willingly ate dinner at our hotel each night because of how wonderful the staff was. Our room was a bit delayed at check in and they went above and beyond to apologize for the inconvenience. Everything was just truly amazing. Even the little details such as sparkling water in the gym."
Mackenzie 2-night trip
Posted less than an hour ago
Omni Chicago 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 $244 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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