Far Southeast Side Vacation Rentals

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Our top choices for Far Southeast Side vacation rentals

Chic Retreat, Chic Retreat "Your Urban Getaway"

Chic Retreat, Chic Retreat "Your Urban Getaway"
Roseland
6.0 out of 10, (4 reviews)
"The host was excellent and she responded to all my questions in an excellent manner. The home was beautiful as pictured. I wouldn’t mind staying there again on my next visit! I parked my car out in front and was no problems the 3 days we were there! "
United States
Keiona W.
$372 nightly
The price is $390
Feb 23 - Feb 24
Total with taxes and fees
Chic Retreat, Chic Retreat "Your Urban Getaway"

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,071 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
$135 nightly
The price is $158
Feb 11 - Feb 12
Total with taxes and fees
Sentral Michigan Avenue

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$159 nightly
The price is $176
Feb 11 - Feb 12
Total with taxes and fees
West Loop Living – Bright 1BR

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$147 nightly
The price is $163
Feb 16 - Feb 17
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (425 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
$185 nightly
The price is $218
Feb 11 - Feb 12
Total with taxes and fees
Level Chicago – Old Town

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$159 nightly
The price is $176
Feb 15 - Feb 16
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$168 nightly
The price is $186
Feb 17 - Feb 18
Total with taxes and fees
Sleek 1BR Apartment w/ In-unit Laundry

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (692 reviews)
"Perfect location and very clean! "
United States
Latoya
$188 nightly
The price is $220
Feb 11 - Feb 12
Total with taxes and fees
Kasa Magnificent Mile Chicago

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$159 nightly
The price is $176
Feb 16 - Feb 17
Total with taxes and fees
Sun-Drenched 1BR Apartment

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$159 nightly
The price is $176
Feb 16 - Feb 17
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 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.
$296 nightly
The price is $330
Feb 19 - Feb 20
Total with taxes and fees
River North Rooftop With In and Out Parking 3

Guild #2 | Gold Coast Mag Mile Best Location

Guild #2 | Gold Coast Mag Mile Best Location
Downtown Chicago
9.8 out of 10, Exceptional, (19 reviews)
"We loved our stay at this property. It’s in a fantastic location and is roomy and comfortable. We would definitely stay again!"
United States
laura s.
$289 nightly
The price is $354
Feb 23 - Feb 24
Total with taxes and fees
Guild #2 | Gold Coast Mag Mile Best Location

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
$132 nightly
The price is $155
Feb 11 - Feb 12
Total with taxes and fees
Wrigleyville Suites

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
$178 nightly
The price is $198
Mar 2 - Mar 3
Total with taxes and fees
Complete 1BR Home Sum

NEW Private West Loop 1br with Backyard near Green Line and CTA

NEW Private West Loop 1br with Backyard near Green Line and CTA
East Garfield Park
9.6 out of 10, Exceptional, (4 reviews)
"Very cozy stay. Host was great with communication and the place has everything needed. Would definitely book here again!"
United States
Eric H.
$195 nightly
The price is $241
Feb 17 - Feb 18
Total with taxes and fees
NEW Private West Loop 1br with Backyard near Green Line and CTA

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
$219 nightly
The price is $251
Feb 25 - Feb 26
Total with taxes and fees
At Home in Oak Park

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
$229 nightly
The price is $269
Feb 27 - Feb 28
Total with taxes and fees
Kasa River North Chicago

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
10.0 out of 10, Exceptional, (4 reviews)
"Comfortable beds, great location"
United States
Jason
$174 nightly
The price is $191
Feb 11 - Feb 12
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit
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

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 $106 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.