Title: Far Southeast Side Vacation Rentals from CA $118: 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)

![](https://images.trvl-media.com/place/829/b4cf8e95-0f92-4795-af28-19f97bbf7dad.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Far Southeast Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-04-17&endDate=2026-04-19&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/faeb35cc.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)

![Interior](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/f2dd2340.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)

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

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

Roseland

6.0/10

(4)

"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 $342

CA $533 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Business Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/c94fe51a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/9649f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ENVITAE Hotel 4 Bedroom Luxury Apartments

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

Near North Side

10/10

Exceptional

(8)

"We loved at our stay at this property. It was one of the best stays we have had on vacation."

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

Javeria

CA $439

CA $804 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/f0d78c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/6aab6223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/w1290h1735x0y538-1e6b1087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/26935b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Less is more! Pet friendly Tiny Home near Chicago! 

[](https://www.expedia.ca/Chicago-Hotels-Less-Is-More-Pet-Friendly-Tiny-Home-Near-Chicago.h103911623.Hotel-Information)

Burr Ridge

9.8/10

Exceptional

(35)

"We loved it!!! Perfect space for the 3 of us area is beautiful!! "

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

Aaliyah G.

CA $142

CA $286 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Less-Is-More-Pet-Friendly-Tiny-Home-Near-Chicago.h103911623.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.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)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.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

(1021)

"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "

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

Deidre

CA $162

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Front of property](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/44167e80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/w1320h783x0y1-af1e2329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Duplex, City View | Shared kitchen](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/14e4f60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/27e8c783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago luxury home suites

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(5)

"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Alex

CA $180

CA $212 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/fb27e879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/c8b54872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/4c1d4299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/34bf7592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek 1BR Apt w/ Laundry

[](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1)

"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."

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

Anonymous traveller

CA $86

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f72f6088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/0412ba3d.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/c64cc369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gold Coast Living: Modern Studio Unit

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

Downtown Chicago

10/10

Exceptional

(5)

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

Seynabou

CA $94

CA $226 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/c52efc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/664fb229.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/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.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

(4)

"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."

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

Jeffrey

CA $86

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/3cc0a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/f642030c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/89a0d93e.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/117000000/116800000/116793100/116793043/8c87c7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 1BR in West Loop

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

Downtown Chicago

10/10

Exceptional

(10)

"Great host comfortable bed close to restaurants and parks"

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

Alana C.

CA $86

CA $230 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/adbf623a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/2e28ea21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/fe11ac9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Modern Luxe Apt with In-Unit Laundry

[](https://www.expedia.ca/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1)

"Great experience for me and my wife I would definitely come back "

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

ShowtimeFam1

CA $86

CA $230 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

![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)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.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/117000000/116800000/116793000/116792936/003c4277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/6b9648de.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)

"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 $86

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cafe](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.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)

### Kasa River North Chicago

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

Downtown Chicago

9.6/10

Exceptional

(182)

"Awesome stay "

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

Sally

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/fd6dad17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/31d1cbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One: A 1BR Stay That Feels Like Home

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(5)

"Very nice condo in a quiet neighborhood"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Patrick

CA $86

CA $230 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

![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)

![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.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)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.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

(405)

"Great location, clean room and friendly staff!"

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

Scott

CA $200

CA $265 total

includes taxes & fees

Dec 28 - Dec 29

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/42661a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/fb9441f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/21564a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/aa9373a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### South Loop Rooftop With In and Out Parking 3

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712525.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(4)

"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Angela M.

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712525.Hotel-Information)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/fc67ec22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/05db8c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/0ba6c337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/ad43adba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern West Loop Gem-City Views & Prime Location 5

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-5.h122181192.Hotel-Information)

Downtown Chicago

8.0/10

Very good

(1)

"Great location, plenty of space and clean home. "

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

Brittany T.

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-5.h122181192.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712542/cc2d32b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712542/bffd365b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712542/cd1bfd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712542/w1036h994x0y0-0d2df3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Private Balcony With In and Out Parking

[](https://www.expedia.ca/Chicago-Hotels-River-North-Private-Balcony-With-InOut-Parking.h117712542.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(3)

"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "

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

Rae M.

[](https://www.expedia.ca/Chicago-Hotels-River-North-Private-Balcony-With-InOut-Parking.h117712542.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/fed5b353.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)

![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/112000000/111830000/111821600/111821529/938700c9.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

9.4/10

Exceptional

(18)

"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 $92

CA $141 total

includes taxes & fees

Dec 31 - Jan 1, 2026

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

![Interior](https://images.trvl-media.com/lodging/124000000/123180000/123174500/123174409/719517aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/124000000/123180000/123174500/123174409/cc4b09db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123180000/123174500/123174409/e55adbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/124000000/123180000/123174500/123174409/4ad9cf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown Chicago Stay with Free In & Out Parking 4

[](https://www.expedia.ca/Chicago-Hotels-Downtown-Chicago-Stay-With-Free-In-Out-Parking-4.h123174409.Hotel-Information)

Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Downtown-Chicago-Stay-With-Free-In-Out-Parking-4.h123174409.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/1310976f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/c0215d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/716fc9f5.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/117000000/116800000/116792800/116792754/a190b9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Complete 1BR Home Sum

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

Downtown Chicago

CA $86

CA $230 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09&regionId=553248635976475411&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Far Southeast Side Hotel Reviews

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"10 out of 10 will definitely be back! "

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

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Clean room...friendly staff"

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"What a great stay!!"

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"Clean room"

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"I prefer Embassy Suite over any hotel. ES does not fail in quality, comfort, cleanliness. We enjoyed Chicago very much. Embassy Suite was in walking distance. Staff were very friendly. "

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

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"."

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg)

### InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Nice place and staff!!"

[](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information)

![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"I loved the balcony the most. 10/10."

[](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Staff was incredibly welcoming upon arrival and was fantastic throughout the stay! Perfect location for walking as well as catching the train, can’t recommend enough"

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

## Explore a world of travel with Expedia

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- [Apartments in Far Southeast Side ](https://expedia.ca/Far-Southeast-Side-Apartments.d553248635976475411-aaApartments.Travel-Guide-Accommodation)
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- [B&B in Far Southeast Side ](https://expedia.ca/Far-Southeast-Side-Bed-And-Breakfast.d553248635976475411-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Far Southeast Side ](https://expedia.ca/Far-Southeast-Side-Guest-Houses.d553248635976475411-aaGuestHouses.Travel-Guide-Accommodation)
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