Holiday Rentals in Far Southeast Side

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Our top choices for Far Southeast Side holiday 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.
The price is €355
includes taxes & fees
11 May - 12 May
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, (1,128 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is €160
includes taxes & fees
12 Apr - 13 Apr
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (458 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is €248
includes taxes & fees
12 Apr - 13 Apr
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
The price is €275
includes taxes & fees
3 May - 4 May
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.
The price is €549
includes taxes & fees
19 Apr - 20 Apr
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
The price is €176
includes taxes & fees
27 Apr - 28 Apr
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.
The price is €103
includes taxes & fees
13 Apr - 14 Apr
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.
The price is €202
includes taxes & fees
12 Apr - 13 Apr
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.
The price is €387
includes taxes & fees
15 Apr - 16 Apr
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
The price is €294
includes taxes & fees
15 Apr - 16 Apr
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.
The price is €157
includes taxes & fees
13 Apr - 14 Apr
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.
The price is €202
includes taxes & fees
12 Apr - 13 Apr
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.
The price is €141
includes taxes & fees
12 Apr - 13 Apr
LIVN West Loop Chicago Queen Superior Studio

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (32 reviews)
"Great location and space ! Will use again "
United States
Vanessa
The price is €149
includes taxes & fees
12 Apr - 13 Apr
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
The price is €184
includes taxes & fees
29 Apr - 30 Apr
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.
The price is €154
includes taxes & fees
12 Apr - 13 Apr
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.
The price is €584
includes taxes & fees
12 Apr - 13 Apr
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
The price is €173
includes taxes & fees
28 Apr - 29 Apr
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.
The price is €257
includes taxes & fees
13 Apr - 14 Apr
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.
The price is €258
includes taxes & fees
14 Apr - 15 Apr
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Far Southeast Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Far Southeast Side holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Far Southeast Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Far Southeast Side holiday rentals we have selected for you start as low as €149 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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.