Photo by Marc Jacobs

Far Southeast Side Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals in Far Southeast Side

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Dining

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (894)
"great food spots all around and beautiful sites to see "
The price is HK$1,119
HK$1,542 total
includes taxes & fees
3 Sept - 4 Sept
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (484)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (350)
"Great stay!"
The price is HK$1,005
HK$1,179 total
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (345)
"A lot of good food options walkable distance. "
The price is HK$1,596
HK$2,048 total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (193)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (633)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is HK$1,005
HK$1,179 total
includes taxes & fees
4 Sept - 5 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (208)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is HK$1,186
HK$1,392 total
includes taxes & fees
14 Sept - 15 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (332)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is HK$1,161
HK$1,363 total
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is HK$1,463
HK$2,107 total
includes taxes & fees
29 Aug - 30 Aug
Wrigleyville Suites
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is HK$1,239
HK$1,455 total
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
1 bedroom, desk, laptop workspace, blackout curtains

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (54)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is HK$659
HK$744 total
includes taxes & fees
29 Aug - 30 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (165)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (132)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is HK$1,185
HK$1,391 total
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel cot, WiFi

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (12)
The price is HK$732
HK$1,760 total
includes taxes & fees
3 Sept - 4 Sept
Charming 2BR in Vibrant Lakeview
Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

8.6 out of 10, Excellent, (16)
"Good experience. Would stay there again "
The price is HK$716
HK$1,576 total
includes taxes & fees
1 Sept - 2 Sept
Clean & Equipped 1BR Apt
Cozy, Fully Set-Up 1BR Space
Fridge, microwave, oven, stovetop

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (17)
"Great place! 15 min walk to Wrigley "
The price is HK$716
HK$1,605 total
includes taxes & fees
3 Sept - 4 Sept
Cozy, Fully Set-Up 1BR Space
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is HK$5,840
HK$9,659 total
includes taxes & fees
1 Sept - 2 Sept
Art Villa
Cozy Studio in Hyde Park-Walk to Lake & University
Microwave, oven, stovetop, coffee/tea maker

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is HK$716
HK$1,499 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Studio in Hyde Park-Walk to Lake & University
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Far Southeast Side Hotel Reviews

Find out more about Far Southeast Side

Find out more about Far Southeast Side

Search for holiday rentals in Far Southeast Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Far Southeast Side using one of the methods below:

  • View our selection of featured holiday rentals in Far Southeast Side
  • Use the map to find apartments and other holiday homes in the Far Southeast Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Far Southeast Side while they last

Look no further and take a look at our great range of rental properties in Far Southeast Side!