Title: Book The Best Hotels in Southwest Side for 2026 from CA $89 - Fully Refundable Options - Expedia.ca

[Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[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)

![](https://images.trvl-media.com/place/5719117/853282cb-4f6d-493a-819e-c77bd49895a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

![](https://images.trvl-media.com/place/5719117/853282cb-4f6d-493a-819e-c77bd49895a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Go beyond your typical stay in Southwest Side

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&travelerType=family_friendly)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&amenities=POOL)

Apart hotel

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&lodging=APART_HOTEL)

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&amenities=SPA_ON_SITE)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&amenities=PETS)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&lodging=APARTMENT)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-19&d2=2026-04-19&lodging=CONDO)

## Check prices for these dates

Tonight

[Apr 3 - Apr 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-04-03&endDate=2026-04-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Apr 4 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-04-04&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Side hotels

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3835h2161x6y0-831944db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/b932f6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/450ed27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Chicago – Midway Airport S by IHG

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

West Lawn

8.2/10

Very good

(1,002 reviews)

"Great staff , enjoyed our stay , very close to where we needed to be "

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

Wafa

CA $147

CA $186 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

![Traditional Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/26ad2ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/acd4cf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Carlton Inn Midway

[](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information)

Archer Heights

6.2/10

(1,000 reviews)

"It is a good place to stay."

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

Paul Adrian

CA $134

CA $158 total

includes taxes & fees

Apr 4 - Apr 5

[](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/84aefbd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/953521af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/a2a4ef31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mini-refrigerator](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Skylark Motel

[](https://www.expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information)

Garfield Ridge

4.8/10

(122 reviews)

"This place should shut down. It is the worst accommodation I have ever stayed at. "

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

Roop

CA $115

CA $135 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information)

![Room, 1 Queen Bed, Jetted Tub](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/2a2055fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/905f8d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/dfae7ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free toiletries, towels](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/62a8a4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rainbow Motel

[](https://www.expedia.ca/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information)

Garfield Ridge

5.6/10

(19 reviews)

"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "

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

Conner

CA $119

CA $140 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a68260d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Downtown Chicago

9.4/10

Exceptional

(2,434 reviews)

"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "

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

Christopher

CA $258

CA $350 total

includes taxes & fees

Apr 6 - Apr 7

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

![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w2990h1178x0y0-a3dcd2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w1201h1722x0y78-8f9c452e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

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

Downtown Chicago

9.4/10

Exceptional

(3,713 reviews)

"Great hotel "

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

Marina

CA $178

CA $249 total

includes taxes & fees

Apr 7 - Apr 8

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

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

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

Downtown Chicago

8.6/10

Excellent

(3,157 reviews)

"Nice location and good hotel"

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

Taneshia

CA $166

CA $194 total

includes taxes & fees

Apr 6 - Apr 7

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

![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/5bee96cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown South Loop

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(1,940 reviews)

"Hotel was really nice"

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

LaCarr

CA $176

CA $206 total

includes taxes & fees

Apr 16 - Apr 17

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ice skating](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/e1a9657a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/3cfba32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silversmith Hotel Chicago Downtown

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

Downtown Chicago

9.2/10

Wonderful

(2,235 reviews)

"Great stay!"

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

Jessica

CA $149

CA $218 total

includes taxes & fees

Apr 12 - Apr 13

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

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/dfb99e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/d37889fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Hotel

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

Downtown Chicago

8.8/10

Excellent

(5,052 reviews)

"very beautiful hotel and great location "

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

Ciandra

CA $152

CA $178 total

includes taxes & fees

Apr 5 - Apr 6

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

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite, Multiple Beds | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/w3837h2559x3y0-81ee3aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago

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

Downtown Chicago

8.6/10

Excellent

(2,716 reviews)

"We love staying here "

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

Carrie

CA $277

CA $366 total

includes taxes & fees

Apr 10 - Apr 11

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

![Shared kitchen](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/1da577c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/12aa85c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/9ef15d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/91aea402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FOUND Hotel Chicago River North

[](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(526 reviews)

"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "

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

William

CA $114

CA $134 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/086ff612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, City View | City view](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/3e0e58e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Congress Plaza Hotel

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

Downtown Chicago

8.0/10

Very good

(10,012 reviews)

"The stay is well worth the affordable price."

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

Thomas

CA $151

CA $177 total

includes taxes & fees

Apr 5 - Apr 6

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

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f0cafd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/d35b9e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f4944277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chicago Hotel Collection Ambassador Gold Coast

[](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(1,344 reviews)

"Very beautiful place to stay"

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

angie

CA $155

CA $182 total

includes taxes & fees

Apr 27 - Apr 28

[](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/w5771h3835x0y5-963f61be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/6b5099c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Chicago - Magnificent Mile

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

Downtown Chicago

8.8/10

Excellent

(2,396 reviews)

"Loved this hotel!"

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

Ellen

CA $159

CA $186 total

includes taxes & fees

Apr 12 - Apr 13

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

![Interior entrance](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/eff99d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Millennium Suite King](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f5de83c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gym](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f052d496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/527277ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Millennium Hotel Knickerbocker Chicago

[](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(1,964 reviews)

"Very small shower, cleanish"

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

Riley

CA $129

CA $185 total

includes taxes & fees

Apr 19 - Apr 20

[](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch LCD TV with cable channels, iPod dock, streaming services](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/c580c0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/48e8b586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/b161c307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Staypineapple, An Iconic Hotel, The Loop

[](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(1,030 reviews)

"Lots of places to eat and shop nearby"

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

Analicia

CA $185

CA $258 total

includes taxes & fees

Apr 26 - Apr 27

[](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information)

![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/6f853099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/95d7089e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/d0c2944a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/0a805224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Central Loop Hotel

[](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(2,056 reviews)

"For the price, it was a very nice a room and location. "

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

Anna

CA $129

CA $151 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information)

![Lobby lounge](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/de4336b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/87314c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/81673aca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Le Méridien Essex Chicago

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(1,001 reviews)

"Great views close to museums and great restaurants "

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

Blanca L

CA $184

CA $240 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.Hotel-Information)

![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/4bc08adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/64fc97f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Single Room](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/b8603e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/5e323fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Godfrey Hotel Chicago

[](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(2,128 reviews)

"Nice place to stay. "

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

Akanksha

CA $139

CA $196 total

includes taxes & fees

Apr 27 - Apr 28

[](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.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=2026-04-17&endDate=2026-04-18&regionId=553248635976475403&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## Stay near popular Great Lakes attractions

### Marquette Park

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=507385)

### S.S. Peter and Paul Church

After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6247219)

### Union Stock Yard Gate

You can find out about the history of Chicago with a trip to Union Stock Yard Gate. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=866963271656538112)

### Ephraim Bajar Cultural Center

Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=1001622631923163136)

### Balzekas Museum of Lithuanian Culture

You can spend time exploring the galleries in Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the riverfront in this vibrant area, or check out its top-notch restaurants. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621555594769)

## Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

[See all hotels in Southwest Side](https://www.expedia.ca/Hotel-Search?startDate=2026-04-17&endDate=2026-04-18&adults=2&regionId=553248635976475403)

![](https://images.trvl-media.com/place/5719117/853282cb-4f6d-493a-819e-c77bd49895a5.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high)

Photo by by Midway Intl Airport

## Top Southwest Side Hotel Reviews

## Recent Reviews in Southwest Side

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg)

### River Hotel

8/10 Good

"The staff was great and very helpful. Both people I talked to were helpful with the check in process and how to figure out parking. I had a couple issues with the room itself. The sink was hard to shut off. If you weren’t paying attention, the sink would be left running just a tiny bit. You had to wiggle the handle around a bunch to get it to finally turn off. The bed wasn’t great for two people. It was pushed right up against the window so the person on the inside could only get in by crawling in at the foot of the bed. I didn’t have that issue when I stayed there a few years ago. Other than those two things I had a very nice stay. The location is perfect and within walking distance to a lot of things. "

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

"Yes"

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

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

### Congress Plaza Hotel

10/10 Excellent

"Stayed here several times. This is the only place I stay in Chicago and always a five star experience!"

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

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

### Embassy Suites by Hilton Chicago Downtown River North

8/10 Good

"It was a very nice, clean property. Room was spotless and stayover service did an awesome job - making the beds and even setting up my children's pillows/"stuffies" nicely on the bed. I would rate it a 5 for service and based on what they have. I rated it an overall 4 because the indoor pool was quite small for the size of the property (about 300 rooms) and the demographic it serves (suites for families - though, I'm sure they get a lot of business travelers). The gym was pretty nice, but, again, it was on the smaller side considering the size of the property. This criticism is more for the basic build of the property which may have been out of the control of the ownership based on design and restrictions they faced with financial backing or the brand itself. I would stay again. It was a great location and an overall nice operation."

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

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg)

### Hotel Felix River North/Magnificent Mile

8/10 Good

"It is in a good location not far from public transit and the magnificent. The coffee in the morning is very good."

[](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

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

### Hilton Chicago

10/10 Excellent

"Emaculate"

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

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

### Eurostars Magnificent Mile

10/10 Excellent

"Nice staff "

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

![The Chicago Hotel Collection Ambassador Gold Coast](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475_y.jpg)

### The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Great amount of space for a downtown hotel, however the room was showing its age with stained furniture, frayed couch covers, and cracks in the wall. Location was great and the bar and lobby are always beautiful. Overall we’d probably stay again but may start looking for other options if updates aren’t made."

[](https://expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

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

### The Wade

8/10 Good

"Clean room, great view, close to lake! Loved! "

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

## More cheap stays in Southwest Side

![Red Roof Inn PLUS+ Chicago - Willowbrook](https://images.trvl-media.com/lodging/1000000/10000/4100/4013/2539e456_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $79

CA $89 total

Apr 10 - Apr 11

includes taxes & fees

6.4/10 (1,084 reviews)

[](https://expedia.ca/Chicago-Hotels-Red-Roof-Inn-PLUS-Chicago-Willowbrook.h4013.Hotel-Information)

![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/6e52464b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $112

CA $125 total

Apr 5 - Apr 6

includes taxes & fees

9/10 Wonderful! (2,666 reviews)

[](https://expedia.ca/Chicago-Hotels-SureStay-Plus-Hotel-By-Best-Western-Chicago-Lombard.h10641.Hotel-Information)

![Sonesta Simply Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/330000/328600/328524/536eba50_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Sonesta Simply Suites Chicago O'Hare Airport

4021 North Mannheim Rd Schiller Park IL

CA $141

CA $162 total

Apr 27 - Apr 28

includes taxes & fees

8.2/10 Very Good! (2,466 reviews)

[](https://expedia.ca/Chicago-Hotels-Sonesta-Simply-Suites-Chicago-OHare.h328524.Hotel-Information)

![Hampton Inn Chicago-O'Hare International Airport](https://images.trvl-media.com/lodging/1000000/20000/14600/14509/5425f524_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $145

CA $166 total

Apr 5 - Apr 6

includes taxes & fees

9.2/10 Wonderful! (2,254 reviews)

[](https://expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-OHare.h14509.Hotel-Information)

![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

CA $157

CA $184 total

Apr 16 - Apr 17

includes taxes & fees

8.2/10 Very Good! (2,673 reviews)

[](https://expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information)

![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

CA $147

CA $186 total

Apr 5 - Apr 6

includes taxes & fees

8.2/10 Very Good! (1,002 reviews)

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

## Hotels in Southwest Side with star rating

![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg)

5 Star Hotels

10 properties

[](https://expedia.ca/5Star-Southwest-Side-Hotels.s50-0-d553248635976475403.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

137 properties

[](https://expedia.ca/4Star-Southwest-Side-Hotels.s40-0-d553248635976475403.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

227 properties

[](https://expedia.ca/3Star-Southwest-Side-Hotels.s30-0-d553248635976475403.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

211 properties

[](https://expedia.ca/2Star-Southwest-Side-Hotels.s20-0-d553248635976475403.Travel-Guide-Filter-Hotels)

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