Title: Far Southeast Side Vacation Home Rentals from CA $234: Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in Far Southeast Side](https://expedia.ca/Far-Southeast-Side-Vacation-Rentals.d553248635976475411.Travel-Guide-VacationRentals)[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 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475411&startDate=2026-04-24&endDate=2026-04-26&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 homes

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/b1ada0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/eaaebb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/d8580e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/48a5d932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Home Away From Home in Sauk Village

[](https://www.expedia.ca/Sauk-Village-Hotels-Pleasant-3-Bedroom-House-In-Sauk-Village.h121815186.Hotel-Information)

Sauk Village

10/10

Exceptional

(1)

"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "

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

Aaron K.

CA $157

CA $234 total

includes taxes & fees

Jan 31 - Feb 1, 2026

[](https://www.expedia.ca/Sauk-Village-Hotels-Pleasant-3-Bedroom-House-In-Sauk-Village.h121815186.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/9d278ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/3c3ca737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/138bf941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/w1200h796x0y4-555fde87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3br home near Chicago, fenced yard for pets

[](https://www.expedia.ca/Richton-Park-Hotels-Spacious-3br-Home-Near-Chicago.h108885786.Hotel-Information)

Richton Park

9.0/10

Wonderful

(14)

"Really cute house! Very comfortable beds. Clean and well maintained. "

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

Samantha D.

CA $148

CA $426 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Richton-Park-Hotels-Spacious-3br-Home-Near-Chicago.h108885786.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h857x0y6-f6fedf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h848x0y11-b9dabcf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h850x0y1-740ec46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122921300/122921247/w1290h850x0y25-29256ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3BR w/Deck · Minutes from I-65\. Fenced Yard

[](https://www.expedia.ca/Merrillville-Hotels-Modern-3BR-WDeck-Minutes-From-I-65-Fenced-Yard.h122921247.Hotel-Information)

Merrilville

CA $203

CA $509 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Merrillville-Hotels-Modern-3BR-WDeck-Minutes-From-I-65-Fenced-Yard.h122921247.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.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)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/f18fcae4.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

9.8/10

Exceptional

(17)

"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."

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

Karen D.

CA $171

CA $245 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w506h639x259y44-83e61931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w508h683x259y0-938c1ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w505h683x260y0-7687ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w505h683x260y0-df8876b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Honeycomb Hideout w/ 2 bedrooms

[](https://www.expedia.ca/Gary-Hotels-Honeycomb-Hideout-W-2-Bedrooms.h88178891.Hotel-Information)

Gary

CA $179

CA $579 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Gary-Hotels-Honeycomb-Hideout-W-2-Bedrooms.h88178891.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/7374e6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/e0894c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/b86200c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/327a76af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dunes Escape - Minutes from Indiana Dunes National Park

[](https://www.expedia.ca/Gary-Hotels-Dunes-Escape-Minutes-From-Indiana-Dunes-National-Park.h83025813.Hotel-Information)

Miller Beach

9.8/10

Exceptional

(36)

"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"

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

Braden S.

CA $110

CA $413 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Gary-Hotels-Dunes-Escape-Minutes-From-Indiana-Dunes-National-Park.h83025813.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/a0f5c46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/49bef28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/1dc70e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/c1640248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*The Comfy King Ranch\*King Bed Suite\*Fast Wi-Fi

[](https://www.expedia.ca/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

Worth

9.6/10

Exceptional

(55)

"Perfect place for an 8 person golf trip! "

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

Griffin P.

CA $219

CA $462 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w867h654x78y17-d683a7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/9878af78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w506h683x260y0-79a3d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w904h683x60y0-33f7d28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coziest estate home 20 minutes to downtown

[](https://www.expedia.ca/Chicago-Hotels-Coziest-Estate-Home-20-Minutes-To-Downtown.h88494875.Hotel-Information)

Willow Springs

8.8/10

Excellent

(16)

"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"

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

Gabriela N.

CA $246

CA $545 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Coziest-Estate-Home-20-Minutes-To-Downtown.h88494875.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/3f6e4959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/c4f6c687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vintage Urban Retreat

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

Oak Park

10/10

Exceptional

(14)

"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."

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

Thomas P.

CA $222

CA $676 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/b80be72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x60y0-4a286511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w906h683x59y0-ad8ac03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x59y0-8cb3eda8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

[](https://www.expedia.ca/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information)

Westchester

9.8/10

Exceptional

(19)

"Great place Great location "

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

Josh W.

CA $221

CA $558 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/e376d974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/dc90b17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/08f64820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/b132ab29_edited_0386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

Maywood

8.0/10

Very good

(20)

"Very nice place "

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

Elliot H.

CA $203

CA $321 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/71fea1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/c86038f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/29e8ad65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/643f9b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enamored in Elmhurst

[](https://www.expedia.ca/Chicago-Hotels-Enamored-In-Elmhurst.h105783565.Hotel-Information)

Elmhurst

10/10

Exceptional

(14)

"Great stay"

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

Aaron B.

CA $291

CA $674 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-Enamored-In-Elmhurst.h105783565.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/010eed58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/b52cb489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/56333a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/7448b12a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

[](https://www.expedia.ca/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.Hotel-Information)

Gary

8.6/10

Excellent

(17)

"i had a good time here. the house was great. thank you"

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

Alvaro C.

CA $204

CA $595 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a03596e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/fcb2b3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/dd9a3475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a531c8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill 

[](https://www.expedia.ca/Gary-Hotels-COMFORTABLE-ALLUSION.h111668679.Hotel-Information)

Gary

10/10

Exceptional

(4)

"Very nice property. Kids loved staying here! "

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

Sydney D.

CA $282

CA $623 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Gary-Hotels-COMFORTABLE-ALLUSION.h111668679.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/1e6ca815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/5ff1a0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/05a2b931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/ccf123af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LUXE 3 BR, 2 BA + Hot Tub

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

Elmhurst

8.8/10

Excellent

(38)

"Great place to stay. Plenty of backyard space. "

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

Terrence M.

CA $197

CA $445 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/c88a9d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/e7e36576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/defb4ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/d590570a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gated Family Home w/ Chef’s Kitchen

[](https://www.expedia.ca/Chicago-Hotels-Gated-Family-Home-W-Chefs-Kitchen.h122731919.Hotel-Information)

Humboldt Park

CA $192

CA $685 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Chicago-Hotels-Gated-Family-Home-W-Chefs-Kitchen.h122731919.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/7407c2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/cb5bf3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/c8a15818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/0900c857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Victorian Vibes ❤️ | Character & Charm 

[](https://www.expedia.ca/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information)

Oak Park

10/10

Exceptional

(28)

"Great location and walkable to restaurants. "

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

Laura B.

CA $283

CA $754 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/w1179h800x21y0-c9fb8097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/d8187eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/45b3ad33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/24a188f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 4BR Retreat Near MDW | LCP Collection

[](https://www.expedia.ca/Chicago-Hotels-Modern-4BR-Retreat-Near-MDW-LCP-Collection.h99269654.Hotel-Information)

Burbank

9.4/10

Exceptional

(6)

"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "

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

Stephanie S.

CA $252

CA $627 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](https://www.expedia.ca/Chicago-Hotels-Modern-4BR-Retreat-Near-MDW-LCP-Collection.h99269654.Hotel-Information)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/de764151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/3337bff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/4b477630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107760000/107751500/107751486/b7079b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

[](https://www.expedia.ca/Gary-Hotels-Tarquatic-Dreamsicle.h107751486.Hotel-Information)

Gary

8.8/10

Excellent

(6)

"Enjoyed staying at this place. Definitely will stay again"

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

Devonta J.

CA $398

CA $884 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Gary-Hotels-Tarquatic-Dreamsicle.h107751486.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/443df914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/074afb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/6d5ce3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/230d1f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Stylish Comfort Near Casino and Hwy

[](https://www.expedia.ca/Chicago-Hotels-Modern-Stylish-Comfort-Near-Casino-And-Hwy.h122655441.Hotel-Information)

Homewood

CA $205

CA $562 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Modern-Stylish-Comfort-Near-Casino-And-Hwy.h122655441.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=2026-01-14&endDate=2026-01-15&regionId=553248635976475411&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cabins

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Villas

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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

![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

"Superb staff, immaculate room"

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

![Homewood Suites by Hilton Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2d5c8626_y.jpg)

### Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent

"Spotless, clean room, accommodating staff, beautiful pool and hot tub area, and competitive rates!"

[](https://expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.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

"Great room. Beautiful building. Very friendly staff."

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

![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg)

### Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent

"Great view of downtown Chicago, easy access to the Mart, and friendly/helpful staff "

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"."

[](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.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

"Staff was great, clean, nice bed"

[](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

"Wonderful breakfast. Friendly and professionally competent staff!"

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

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Good Service "

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

"Very nice views."

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

## Find out more about Far Southeast Side

## Far Southeast Side Vacation Homes information

| Number of reviews | 256                |
| ----------------- | ------------------ |
| Accommodation     | 325 Vacation Homes |
| Lowest Price      | CA $234            |
| Highest Price     | CA $884            |

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- [Visit West Pullman ](https://www.expedia.ca/Chicago-West-Pullman.dx6132214)
- [Irondale Vacations ](https://www.expedia.ca/Irondale.d6132291.Destination-Travel-Guides)

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