Photo by Marc Jacobs

Far Southeast Side Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Far Southeast Side

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is S$210
includes taxes & fees
25 Nov - 26 Nov
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is S$89
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is S$191
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (332)
"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is S$300
includes taxes & fees
25 Nov - 26 Nov
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is S$183
includes taxes & fees
24 Dec - 25 Dec
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"The room is really cute and has all the amenities (including washing machine and dishwasher). Staying for business though I could hear quite a lot of noise from other rooms which made sleeping difficult at night "
The price is S$220
includes taxes & fees
23 Dec - 24 Dec
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is S$215
includes taxes & fees
23 Dec - 24 Dec
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is S$137
includes taxes & fees
8 Dec - 9 Dec
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is S$177
includes taxes & fees
23 Dec - 24 Dec
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is S$201
includes taxes & fees
23 Dec - 24 Dec
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (33)
"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...
The price is S$250
includes taxes & fees
17 Dec - 18 Dec
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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.
Don't see what you're looking for?
See all available properties in Far Southeast Side
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Far Southeast Side you may be interested in

Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8193)
"Ice machines! This was an issue here all summer long. I pointed it out to management over the summer but the issue has gone from bad to worse. Supposedly, there are ice machines on even floors. This visit, housekeeping directed me to the machine on the 4th floor as the only working ice machine. I suggest that as a minimum, correct the signs on all floors that do not have operable ice machines. "
The price is S$204
includes taxes & fees
4 Dec - 5 Dec
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3567)
"Highly recommend ."
The price is S$158
includes taxes & fees
23 Dec - 24 Dec
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Premium bedding, in-room safe, desk, laptop workspace

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3291)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."
The price is S$152
includes taxes & fees
23 Dec - 24 Dec
Club Quarters Hotel, Central Loop, Chicago
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals