Title: Hotels by Destination Hotels in Southwest Side from CA $238 | Expedia.ca

[Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides)

![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

# Find Hotels by Destination Hotels in Southwest Side from CA $238

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## Check prices for these dates

Tonight

[Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Side Destination Hotels

![2 restaurants, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/d313af43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/56ac30bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/4c4241f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/392edec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Athletic Association, a Hyatt Hotel

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Athletic-Association.h1118328.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(1002)

"It’s amazing historical property "

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

Joel

CA $161

CA $238 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Athletic-Association.h1118328.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Top Southwest Side Hotel Reviews

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"Everyone was nice and helpful. Room was clean and the hotel location is great"

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

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"The room was amazing, views were amazing, staff is very friendly and helpful, I’m definitely coming back here for sure ."

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Staff was so amazing nice and helpfuk"

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

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

### Hilton Chicago

10/10 Excellent

"Amazing experience! The rooms were spotless, comfortable, and thoughtfully maintained. All hotel amenities were clean, well-organized, and ready to use. The breakfast was excellent, with a great variety of options to choose from. What truly made this stay extraordinary was the outstanding service. Brad, Vicente, Cruz, Eric, Ruby, and the entire team went above and beyond to ensure a memorable experience. Their professionalism, kindness, and attention to detail were exceptional. Without a doubt, this was a unique and unforgettable stay — truly a hotel that exceeds five-star expectations. ❤️"

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

"The staff went above and beyond for us. We got in real late after midnight and they were extremely accommodating. Since we were flying all day on my fiancé birthday i had asked for them to leave a little happy birthday note in the room when we arrived. They left a birtday card and a box of whoppers for her. That was amazing. The whole staff was top notch. "

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

"The room was clean, but basic. The restaurant and food was great. The staff were very helpful and most were friendly. The location was excellent, a safe neighborhood with many restaurants and nice stores including Whole Foods in short walking distance. I'd stay here again. Try eating at Meli and Nancy's Pizza."

[](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

"Yes room was clean ans staff great"

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

"From beginning to end it was awesome.....Except for parking it was horrible I got lost for about 30 mins trying to find my rental....BUT the 🏨 employees were all very helpful and we found it in no time after that ❤️.....The 🏨 was awesome, views ❤️ and the vibe was on point everything was at a walking distance 🥰.... Beautiful city day or 🌃 please preserve it as much as you can. I'm from California and greatly appreciate the hospitality ❤️ 🙏"

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

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

### Eurostars Magnificent Mile

10/10 Excellent

"Loved this hotel. The only thing I disliked was not having a microwave in my room. I ate out daily but sometimes did not finish my food and would have to throw it out due to not having anything to reheat it. The fridge was so stocked with their items that there was barely room to put your own stuff in there. "

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

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