Title: Chicago Vacation Home Rentals from CA $272: Search Top Private Vacation Homes for Rent | Expedia.ca

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![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chicago vacation homes

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-5a95ad03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-bd552f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-7ee1aa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-2c40f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Shore

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information)

CA $57

CA $643 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information)

![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)

![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/47ba5585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122740000/122732000/122731919/7e3db215.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/c88a9d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Humboldt Park

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

CA $172

CA $669 total

includes taxes & fees

Jan 19 - Jan 20

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

![Dining](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d658c7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/3081c65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/a541fdcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/3eea93c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information)

CA $199

CA $339 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/b289aa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/069d828a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/bb6345e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/f7cf3b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gages Lake

[](https://www.expedia.ca/Chicago-Hotels-Newly-Remodeled-Near-Lake-4BR-W-Hot-Tub-Games.h122068878.Hotel-Information)

10/10

Exceptional

(1 review)

"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "

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

Danielle S.

CA $153

CA $746 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Newly-Remodeled-Near-Lake-4BR-W-Hot-Tub-Games.h122068878.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w905h683x59y0-1e5c290a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w756h683x134y0-73459ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w507h683x258y0-bb141c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w903h683x61y0-6bb2c68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in La Grange Highlands

[](https://www.expedia.ca/Chicago-Hotels-Guesthouse-Gem-2BR.h117975506.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."

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

Arnie B.

CA $125

CA $361 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Guesthouse-Gem-2BR.h117975506.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/7966b3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/5445a025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/2718fcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/3e0125af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mundelein

[](https://www.expedia.ca/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information)

9.8/10

Exceptional

(68 reviews)

"Super cozy!! The neighborhood is so so so lovely! "

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

Andrea M.

CA $187

CA $461 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w903h683x60y0-f205b528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w908h683x58y0-0a2075c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w905h683x59y0-f1a47515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w905h683x60y0-d3c62524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westmont

[](https://www.expedia.ca/Chicago-Hotels-Back-Unit-Patio.h120544690.Hotel-Information)

CA $149

CA $389 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Back-Unit-Patio.h120544690.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/125000000/124570000/124564900/124564816/225ce55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/125000000/124570000/124564900/124564816/1115f2a0.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/125000000/124570000/124564900/124564816/d7f2ce9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/125000000/124570000/124564900/124564816/4426cd44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Willow Springs

[](https://www.expedia.ca/Chicago-Hotels-Cozy-2-Bedroom-Estate-In-Charming-Willow-Springs.h124564816.Hotel-Information)

10/10

Exceptional

(1 review)

"Host was great at communicating throughout the process. House was perfect. Great yard for the dogs and looks to be recently updated and very clean. Wasn’t a fan of being forced into the insurance or they take a big deposit when you book but don’t know if that is this listing or a VRBO thing. Still besides that it was perfect. Would definitely stay again. "

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

Raymond H.

CA $205

CA $439 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Cozy-2-Bedroom-Estate-In-Charming-Willow-Springs.h124564816.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/acc33991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/feda95b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/fba7b9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/337409c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Portage Park

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.Hotel-Information)

CA $206

CA $1,207 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/411ffb8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/704b617f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/07286fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/c519faca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Austin

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-7BR-Gym-Game-Room-Theater.h122811950.Hotel-Information)

CA $194

CA $1,236 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-7BR-Gym-Game-Room-Theater.h122811950.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/139d9ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, dishwasher, coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/d880898a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/bb724005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122670000/122663000/122662962/928e7842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Wrigley-Field-Townhouse-W-Pool-Table.h122662962.Hotel-Information)

CA $171

CA $842 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Wrigley-Field-Townhouse-W-Pool-Table.h122662962.Hotel-Information)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/7199850c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/03c44db0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/d2a4fb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/cbb8c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Chicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-Upgrade-Near-Navel-Base-Sauna.h118074409.Hotel-Information)

9.8/10

Exceptional

(18 reviews)

"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "

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

Thomas D.

CA $174

CA $721 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Modern-Upgrade-Near-Navel-Base-Sauna.h118074409.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/079e5c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/ca60baaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Riverwoods

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

9.8/10

Exceptional

(76 reviews)

"Amazing area, loved the feel of it all and very quiet neighborhood."

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

Joshua K.

CA $136

CA $272 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.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)

![Interior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/524cef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/340d0fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/839ff6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Elmhurst

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

10/10

Exceptional

(15 reviews)

"Clean rooms, very helpful and friendly host, the house had everything we needed"

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

Kaitlyn M.

CA $328

CA $728 total

includes taxes & fees

Jan 19 - Jan 20

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

![Paper towels, dining tables](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496906/w905h683x60y0-969d6891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496906/w904h683x60y0-75e223bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496906/w904h683x60y0-65480874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496906/w905h683x60y0-9f601b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in wheaton

[](https://www.expedia.ca/Chicago-Hotels-Spacious-Quaint-Home-Game-Room-LOTS-Of-Beds.h104496906.Hotel-Information)

10/10

Exceptional

(1 review)

"Perfect house for our family trip. Plenty of space for everyone. "

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

Kristine T.

CA $233

CA $608 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Spacious-Quaint-Home-Game-Room-LOTS-Of-Beds.h104496906.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/w4000h2707x0y0-0d2f41b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/32f3ec4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/w4000h2785x0y0-d24b5b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/fe27c4de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waukegan

[](https://www.expedia.ca/Chicago-Hotels-Value-Stay-Unfurnished-Home-Bring-Own-Sleeping-Beds-Or-Ask-For-Airbed-Wifi.h121605980.Hotel-Information)

8.8/10

Excellent

(3 reviews)

"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "

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

You Tha Truth B.

CA $174

CA $377 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Chicago-Hotels-Value-Stay-Unfurnished-Home-Bring-Own-Sleeping-Beds-Or-Ask-For-Airbed-Wifi.h121605980.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/91000000/90010000/90005100/90005028/2d2b4785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/91000000/90010000/90005100/90005028/3e23ebb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90010000/90005100/90005028/b8014c8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90010000/90005100/90005028/51c8b5b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Carol Stream

[](https://www.expedia.ca/Chicago-Hotels-Beautiful-House-Near-Downtown-Chicago.h90005028.Hotel-Information)

9.6/10

Exceptional

(4 reviews)

"The property was nice. Perfect for our guys trip. "

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

Jay S.

CA $152

CA $686 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Beautiful-House-Near-Downtown-Chicago.h90005028.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)

![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)

![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)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w903h683x60y0-a4b1b07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westchester

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

9.8/10

Exceptional

(19 reviews)

"Great place Great location "

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

Josh W.

CA $232

CA $597 total

includes taxes & fees

Jan 20 - Jan 21

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

![Dining](https://images.trvl-media.com/lodging/110000000/109210000/109209300/109209297/f6d60f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109210000/109209300/109209297/bcceac0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109210000/109209300/109209297/4435da80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109210000/109209300/109209297/4a5fa6a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Evanston

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Private-Spacious-6-Bedroom-Duplex-With-Parking-In-Charming-Evanston.h109209297.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"Good place to hang out with friends."

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

Brendan W.

CA $796

CA $1,482 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Private-Spacious-6-Bedroom-Duplex-With-Parking-In-Charming-Evanston.h109209297.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/108000000/107130000/107129900/107129829/2bf253d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107130000/107129900/107129829/72078c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/108000000/107130000/107129900/107129829/ce5ea295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/108000000/107130000/107129900/107129829/f0ba7894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Burbank

[](https://www.expedia.ca/Chicago-Hotels-Cozy-House-In-The-City.h107129829.Hotel-Information)

9.6/10

Exceptional

(10 reviews)

"The entire process was effortless. The property exceeded my expectations."

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

Toneal

CA $296

CA $616 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Cozy-House-In-The-City.h107129829.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=2026-01-29&endDate=2026-01-30&regionId=178248&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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Cabins

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Private vacation homes

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Condos

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Villas

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Cottages

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Residences

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## Top Chicago Hotel Reviews

![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

"Very nice, check-in and check out fast and efficient. Staff very helpful and welcoming "

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

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Clean accommodations and friendly staff."

[](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.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

"The room was clean. The staff was friendly. The breakfast was not great, but not bad. "

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

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Our stay was A+, the staff was courteous and helpful and always went above and beyond in service. The location was great across from the Riverwalk and central to many other Chicago attractions. We will be back!!"

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg)

### Hilton Chicago O'Hare Airport

10/10 Excellent

"Stayed prior to flight, clean, quiet room!"

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information)

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

### Hilton Chicago

10/10 Excellent

"Nice size rooms, accommodating check in help, and great location "

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

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg)

### DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"Very good "

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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

"Great location. Hotel was clean and comfortable. Staff were very friendly and welcoming. Only problem is that I paid for parking ($92) with my reservation thru Hotels.com and now I see on my credit card that the hotel also charged me for parking. Now I have to fix that problem. "

[](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

"Girls trip / business meeting "

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

## Find out more about Chicago

## Chicago Vacation Homes information

| Number of reviews | 210                |
| ----------------- | ------------------ |
| Accommodation     | 822 Vacation Homes |
| Lowest Price      | CA $272            |
| Highest Price     | CA $1,482          |

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- [Hotels with Bar in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Bar.0-n800024-0-tHotelswithBar.Travel-Guide-Filter-Hotels)
- [Hotels with Free Airport Shuttle in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Airport-Shuttle.0-n800024-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Breakfast.0-n800024-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Hotels with Free Parking in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Parking.0-n800024-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels)
- [Hotels with Hot Tubs in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Hot-Tubs.0-n800024-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Hotels with an Indoor Pool in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n800024-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
- [Hotels with Tennis Courts in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n800024-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels)
- [Kimpton Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Kimpton-Hotels.0-n800024-0--bKimptonHotels.Travel-Guide-Filter-Hotels)
- [Lake Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Lake-Hotels.0-n800024-0-tLakeHotels.Travel-Guide-Filter-Hotels)
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- [Marriott Hotels & Resorts in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Oceanfront-Hotels.0-n800024-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Pet-Friendly-Hotel.0-n800024-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Romantic-Hotel.0-n800024-0-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [Shopping Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Shopping-Hotel.0-n800024-0-tShoppingHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Spa-Hotel.0-n800024-0-tSpaHotel.Travel-Guide-Filter-Hotels)
- [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Theatre District ](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Cheap-Hotels.0-n651190586167894016-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Theatre District ](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Luxury-Hotel.0-n651190586167894016-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Theatre District Hotels ](https://www.expedia.ca/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels)
- [Houseboats in Washington-Wells Station ](https://www.expedia.ca/Washington-Wells-Station-Houseboats.d6210331-aaHouseboats.Travel-Guide-Accommodation)

- [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

- [Cibc Theatre ](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction)
- [Visit Downtown Chicago ](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699)
- [Visit The Loop ](https://www.expedia.ca/Chicago-The-Loop.dx800024)
- [Millennium Park ](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Richard J. Daley Center ](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction)
- [The Loop Vacations ](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides)

- [Alamo Rent A Car Rental Cars in The Loop ](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c6.Car-Rental-Guide-Suppliers)
- [Avis Rental Cars in The Loop ](https://www.expedia.ca/Avis-Car-Rentals-In-The-Loop.d800024-c41.Car-Rental-Guide-Suppliers)
- [Car rentals near Richard J. Daley Center ](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide)
- [Car rentals near The Loop ](https://www.expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide)
- [Dollar Rent A Car Rental Cars in The Loop ](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c43.Car-Rental-Guide-Suppliers)
- [Enterprise Rental Cars in The Loop ](https://www.expedia.ca/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers)
- [Fox Rental Cars Rental Cars in The Loop ](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-The-Loop.d800024-c19.Car-Rental-Guide-Suppliers)
- [Oryx Rent A Car Rental Cars in The Loop ](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c1059.Car-Rental-Guide-Suppliers)
- [Payless Rental Cars in The Loop ](https://www.expedia.ca/Payless-Car-Rentals-In-The-Loop.d800024-c38.Car-Rental-Guide-Suppliers)
- [Rent A Wreck Rental Cars in The Loop ](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-The-Loop.d800024-c33.Car-Rental-Guide-Suppliers)
- [Routes Rental Cars in The Loop ](https://www.expedia.ca/Routes-Car-Rentals-In-The-Loop.d800024-c1101.Car-Rental-Guide-Suppliers)
- [Sixt Rental Cars in The Loop ](https://www.expedia.ca/Sixt-Car-Rentals-In-The-Loop.d800024-c35.Car-Rental-Guide-Suppliers)
- [Thrifty Car Rental Rental Cars in The Loop ](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-The-Loop.d800024-c45.Car-Rental-Guide-Suppliers)

- [Book Vacation Homes in Chicago on Expedia.com ](https://www.expedia.com/Chicago-Private-Vacation-Homes.d178248-aaPrivateVacationHomes.Travel-Guide-Accommodation)