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Far Southeast Side Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Far Southeast Side holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,216 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is HK$1,185
HK$1,622 total
includes taxes & fees
17 Aug - 18 Aug
Sentral Michigan Avenue
Property grounds

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
9.8 out of 10, Exceptional, (27 reviews)
"I had a fun stay "
United States
Jusu K.
The price is HK$1,247
HK$1,704 total
includes taxes & fees
17 Aug - 18 Aug
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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.
The price is HK$745
HK$1,972 total
includes taxes & fees
11 Aug - 12 Aug
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$2,658
HK$3,556 total
includes taxes & fees
23 Jul - 24 Jul
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (13 reviews)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
The price is HK$1,294
HK$1,722 total
includes taxes & fees
19 Jul - 20 Jul
LIVN West Loop Chicago Queen Superior Studio
Smart TV

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
The price is HK$706
HK$1,948 total
includes taxes & fees
26 Jul - 27 Jul
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
TV

BF - Bright and Cozy 1BR Apartment in Logan Square!

BF - Bright and Cozy 1BR Apartment in Logan Square!
Logan Square
10.0 out of 10, Exceptional, (53 reviews)
"Perfect location for a peaceful stay in Chicago! Great place, great decoration, amenities, and Joan is a fantastic host. Highly recommended! "
United Kingdom
Fernando J.
The price is HK$627
HK$1,487 total
includes taxes & fees
19 Jul - 20 Jul
BF - Bright and Cozy 1BR Apartment in Logan Square!
Games room

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is HK$886
HK$2,384 total
includes taxes & fees
10 Aug - 11 Aug
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Dining

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
8.8 out of 10, Excellent, (3 reviews)
"I called the host about the thermostat not working and he said he would get in touch with somebody, never heard back from him and the problem was never solved. There were two window air conditioning units that I cleaned the filters myself as they were not very efficient."
United States
Raymond
The price is HK$487
HK$2,867 total
includes taxes & fees
19 Jul - 20 Jul
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Iron/ironing board, travel cot, free WiFi, bed sheets

Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (3 reviews)
"We had a great time at this property! After our previous rental cancelled at the last minute, we found this gem and couldn’t have been happier. Communication was clear, check-in was easy, and the property was clean and comfortable. Thanks for a great stay!"
United States
Emily G.
The price is HK$367
HK$2,085 total
includes taxes & fees
27 Jul - 28 Jul
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
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.
The price is HK$651
HK$904 total
includes taxes & fees
22 Jul - 23 Jul
Beautiful Rustic Cabin for Two!
Private kitchen

Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
9.0 out of 10, Wonderful, (2 reviews)
"The host was very friendly and helpful. There was a massive storm before and the host accommodated us with everything we needed"
United States
Bailey H.
The price is HK$1,080
HK$1,323 total
includes taxes & fees
22 Jul - 23 Jul
Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Coffee/tea maker, fridge, microwave, oven

Stylish friendly 3BR Suite near McCormick

Stylish friendly 3BR Suite near McCormick
Near South Side
Stylish friendly 3BR Suite near McCormick
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (502 reviews)
"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."
United States
Serigne abdou
The price is HK$2,194
HK$2,769 total
includes taxes & fees
17 Aug - 18 Aug
Level Chicago – Old Town
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, (87 reviews)
"Wonderful hosts…very kind and communicative. Awesome area… highly recommended!"
United States
Andrew C.
The price is HK$847
HK$1,528 total
includes taxes & fees
27 Jul - 28 Jul
Cozy studio in Andersonville Chicago
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, (67 reviews)
"Very nice stay. Close to everything. Host very helpful. "
United States
Tamela S.
The price is HK$917
HK$2,046 total
includes taxes & fees
17 Aug - 18 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (12 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is HK$5,927
HK$11,117 total
includes taxes & fees
13 Aug - 14 Aug
Modern West Loop Gem-City Views & Prime Location 4
Coffee/tea maker, fridge, microwave, oven

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is HK$1,098
HK$2,639 total
includes taxes & fees
17 Aug - 18 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!
1 bedroom, iron/ironing board, travel cot, 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)
The price is HK$1,223
HK$1,629 total
includes taxes & fees
19 Jul - 20 Jul
LIVN West Loop Chicago Classic Queen Studio
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.
The price is HK$720
HK$2,529 total
includes taxes & fees
6 Aug - 7 Aug
Sleeps 7 • Huge Projector • Designated Workspace
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Our room on the 26th floor was outstanding!!! We went to breakfast early because the first morning was a zoo with children running around and absent parents. Scrambled eggs are always tricky when made for 100 people but the hot sauce made them edible. Traffic pattern at breakfast was a bit congested with people going in all directions at once."
Norman 3-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

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