Title: Far Southeast Side Vacation Rentals from CA $132: Short-Term Rentals for 2026 | Expedia.ca

[Far Southeast Side Travel Guide](https://expedia.ca/Far-Southeast-Side.dx553248635976475411)[Hotels in Far Southeast Side](https://expedia.ca/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[Flights to Far Southeast Side](https://expedia.ca/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[Far Southeast Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southeast-Side.d553248635976475411.Car-Rental-Guide)[Far Southeast Side Vacation Packages](https://expedia.ca/Far-Southeast-Side.d553248635976475411.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Far Southeast Side vacation rentals

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/c9bd722f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/11170f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/d31527c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/eedcca40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Retreat, Chic Retreat "Your Urban Getaway"

[](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat.h111903171.Hotel-Information)

Roseland

6.0/10

(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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Keiona W.

CA $381

CA $590 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat.h111903171.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/f6d9d5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,115 reviews)

"Clean spacious my go to vacation spot all year around "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

xavier

CA $164

CA $233 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/d03e88da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(453 reviews)

"Staff was really nice"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anita

CA $226

CA $299 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b56ca762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/4fcb7f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

[](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(8 reviews)

"Great communication and hosts. Location and unit was perfect."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Greg C.

CA $122

CA $276 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/afe63d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/143f3ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/e3efb27d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/19144195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Comfort: 1BR Unit w/ Laundry

[](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(16 reviews)

"Great host comfortable bed close to restaurants and parks"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alana C.

CA $122

CA $279 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782332/afffc063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782332/26c34829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782332/f1680a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782332/c0506826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 2BR Retreat Near Old Town & Lincoln Park

[](https://www.expedia.ca/Chicago-Hotels-2BR-City-Escape-Bright.h117782332.Hotel-Information)

Near North Side

10/10

Exceptional

(12 reviews)

"Great stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aimee B.

CA $189

CA $519 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Chicago-Hotels-2BR-City-Escape-Bright.h117782332.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/7d7ccc69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c6bb5c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a5975d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

[](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

Downtown Chicago

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler B.

CA $122

CA $276 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d8e9b0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/57a172f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/a410264a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/6c271db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 3

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

Downtown Chicago

9.6/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer M.

CA $222

CA $639 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/74a78a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Studio, 1 King Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | In-room dining](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/7934883a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gym](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/43496058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/24b549c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa South Loop Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-South-Loop-Chicago.h29433443.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(421 reviews)

"Shops nearby, clean apartment, good heat/AC, extremely soft beds and great views! A great place to stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Theresa

[](https://www.expedia.ca/Chicago-Hotels-Kasa-South-Loop-Chicago.h29433443.Hotel-Information)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/7a65e5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f0a938f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/df8744f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1c0ee66d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Studio in the Heart of the Gold Coast

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5 reviews)

"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brianna K.

CA $149

CA $295 total

includes taxes & fees

Apr 27 - Apr 28

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/e8f7392e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/8bacadce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/32a236ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/cf7a7d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern West Loop Gem-City Views & Prime Location 6

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-6.h122181232.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(17 reviews)

"Great place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel L.

CA $280

CA $872 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-6.h122181232.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/01933d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/ee53c125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/ded3c13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/4eee2579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Rustic Cabin for Two!

[](https://www.expedia.ca/Griffith-Hotels-Beautiful-Rustic-Cabin-For-Two.h111821529.Hotel-Information)

Griffith

9.0/10

Wonderful

(21 reviews)

"Nice and cozy place to stay. We enjoyed our secluded area during our time here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Allison A.

CA $115

CA $160 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Griffith-Hotels-Beautiful-Rustic-Cabin-For-Two.h111821529.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/ce588c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/92c646c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/13dc1926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/9f7e92a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4BR Central Apartment w/ Skyline Views

[](https://www.expedia.ca/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.Hotel-Information)

Near North Side

10/10

Exceptional

(12 reviews)

"Great location, comfortable room, welcoming host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Treseanne A.

CA $204

CA $638 total

includes taxes & fees

Apr 26 - Apr 27

[](https://www.expedia.ca/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/074854f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/715ba83d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/b2e3ba0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/d6df8cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy, Comfortable and Convenient apartment. Close to everything!

[](https://www.expedia.ca/Chicago-Hotels-Cozy.h45886096.Hotel-Information)

Oak Park

9.8/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan G.

CA $150

CA $412 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-Cozy.h45886096.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/5893f531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/c185e671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/65038522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/2caa1de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN West Loop Chicago Queen Superior Studio

[](https://www.expedia.ca/Chicago-Hotels-LIVN-West-Loop-Chicago-Queen-Superior-Studio.h126868503.Hotel-Information)

Downtown Chicago

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle R.

CA $188

CA $255 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-LIVN-West-Loop-Chicago-Queen-Superior-Studio.h126868503.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/45434900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft)](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/023c5e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft)](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/dfb80f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/167883c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak Park Loft

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Good location, nice neighborhood, restaurants close"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda

CA $167

CA $345 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

![Iron/ironing board, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/bfe9ce5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/bd243cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/017a65ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/w1017h1536x0y0-87b71443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Uptown Studio Gem Sum

[](https://www.expedia.ca/Chicago-Hotels-Uptown-Studio-Gem-Sum.h116793093.Hotel-Information)

Uptown

7.4/10

Good

(6 reviews)

"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Darryl C.

CA $130

CA $272 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-Uptown-Studio-Gem-Sum.h116793093.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e3fd1233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/da25d2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

[](https://www.expedia.ca/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

Robertsdale

9.6/10

Exceptional

(23 reviews)

"I had a fun stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jusu K.

CA $173

CA $248 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/88e54d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Apartment, 1 King Bed with Sofa bed, Pool Access (Self Check-in with Virtual Front Desk) | Living area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/2969f0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.6/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daysha

CA $184

CA $330 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/1897ede8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/43d43840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/83c9368f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/fca43c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish and Roomy 2BR in Chicago

[](https://www.expedia.ca/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.Hotel-Information)

Edgewater

9.0/10

Wonderful

(14 reviews)

"Clean room, easy, check-in, great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

brent w.

CA $121

CA $298 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.Hotel-Information)

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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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cabins

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Cottages

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Condos

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Private vacation homes

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## Top Far Southeast Side Hotel Reviews

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg)

### Congress Plaza Hotel

8/10 Good

"Small rooms"

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

8/10 Good

"We stayed 5 days our room was cleaned each day! We had a great stay!"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg)

### The Wade

10/10 Excellent

"No water view"

[](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

8/10 Good

"The staff was very friendly and helpful. "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a_y.jpg)

### Aloft Chicago Mag Mile

10/10 Excellent

"Amazing hotel and rooms smelled so clean. Breakfast was good quality! Definitely will be staying here again"

[](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Christian was a wonderful help. "

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/fa2dd97c_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Love it here! We stay here often when we come home to Chicago. Great location, fairly large rooms, clean and accessible. "

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Clean room, gray lobby and nice bar with excellent bartender, breakfast was very good ! "

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b_y.jpg)

### Swissotel - Chicago

4/10 Poor

"Some issues with the room and internet, had to switch rooms. The second room had a malfunctioning toilet fill valve, it would shut off due to friction, requiring me to pull the lid and jiggle it to fill. Some outlet's didn't work. Low hanging fruit that can be attended to can go a long way. Staff was friendly and professional at all times. Would definitely stay here again, but urge attention to detail. Also, have a daily Urban Experience Fee on the final bill that I have asked to get back. Not sure what an Urban Experience Fee means, no Urban Experience was offered outside of doing my thing, being a native Chicagoan. "

[](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

## Find out more about Far Southeast Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Far Southeast Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Apartments in Far Southeast Side ](https://expedia.ca/Far-Southeast-Side-Apartments.d553248635976475411-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Far Southeast Side ](https://expedia.ca/Far-Southeast-Side-Private-Vacation-Homes.d553248635976475411-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Motels in Far Southeast Side ](https://expedia.ca/Far-Southeast-Side-Motels.d553248635976475411-aaMotels.Travel-Guide-Accommodation)
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- [Dollar Rent A Car Car Rentals In Central Chicago](https://expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Central-Chicago.d553248635976475413-c43.Car-Rental-Guide-Suppliers)

Packages

- [Art Institute of Chicago](https://expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
- [United Center](https://expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
- [Navy Pier](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)
- [Lincoln Park Zoo](https://expedia.ca/Lincoln-Park-Zoo-Lincoln-Park.d6065147.Vacation-Attraction)
- [Chicago Riverwalk](https://expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction)
- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Water Tower Place](https://expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)
- [Millennium Park](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Wrigley Field](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

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