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.
$401 nightly
The price is $420
Apr 16 - Apr 17
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, (1,127 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
$159 nightly
The price is $187
Apr 12 - Apr 13
Total with taxes and fees
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (456 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
$247 nightly
The price is $290
Apr 12 - Apr 13
Total with taxes and fees
Level Chicago – Old Town

MTM Premier Funky Jungle sleeps 4 in a charming log cabin with serene lakefront views. Rustic yet comfortable, ideal for small families or groups, with access to campground amenities and seasonal activities.

MTM Premier Funky Jungle sleeps 4 in a charming log cabin with serene lakefront views. Rustic yet comfortable, ideal for small families or groups, with access to campground amenities and seasonal activities.
Portage
10.0 out of 10, Exceptional, (2 reviews)
"We liked the location and all of the amenities. "
United States
Cindy
$271 nightly
The price is $304
May 3 - May 4
Total with taxes and fees
MTM Premier Funky Jungle sleeps 4 in a charming log cabin with serene lakefront views. Rustic yet comfortable, ideal for small families or groups, with access to campground amenities and seasonal activities.

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (18 reviews)
"Great place"
United States
Daniel L.
$582 nightly
The price is $648
Apr 19 - Apr 20
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
$180 nightly
The price is $211
Apr 30 - May 1
Total with taxes and fees
Kasa River North Chicago

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
9.0 out of 10, Wonderful, (22 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
$103 nightly
The price is $115
Apr 12 - Apr 13
Total with taxes and fees
Beautiful Rustic Cabin for Two!

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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.
$207 nightly
The price is $232
Apr 12 - Apr 13
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space

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.
$408 nightly
The price is $457
Apr 14 - Apr 15
Total with taxes and fees
River North Rooftop With In and Out Parking 3

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Plymouth Collection: 2BD with Lobby, Gym, Rooftop
Downtown Chicago
$300 nightly
The price is $331
Apr 12 - Apr 13
Total with taxes and fees
Plymouth Collection: 2BD with Lobby, Gym, Rooftop

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
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
$160 nightly
The price is $179
Apr 13 - Apr 14
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$207 nightly
The price is $232
Apr 13 - Apr 14
Total with taxes and fees
West Loop Living – Bright 1BR

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
$135 nightly
The price is $160
Apr 12 - Apr 13
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (31 reviews)
"Great location and space ! Will use again "
United States
Vanessa
$112 nightly
The price is $132
Apr 14 - Apr 15
Total with taxes and fees
Wrigleyville Suites

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
$187 nightly
The price is $210
Apr 26 - Apr 27
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
$159 nightly
The price is $176
Apr 12 - Apr 13
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry

Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (18 reviews)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
$596 nightly
The price is $682
Apr 12 - Apr 13
Total with taxes and fees
Chic 3bed 2bath Home with free parking close to United Center

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (32 reviews)
"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "
United States
Lisa
$178 nightly
The price is $198
Apr 13 - Apr 14
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
$250 nightly
The price is $286
Apr 13 - Apr 14
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (66 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
$247 nightly
The price is $305
Apr 12 - Apr 13
Total with taxes and fees
2-bedroom apartment just 2 minutes drive to Wrigley Field
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 $132 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.