Title: Top 10 Hotels in Southwest Side from $52 - Competitive Prices | Expedia.com

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

![Chicago, IL which includes landscape views and an airport](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

Pet-friendly

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&amenities=PETS)

Pool

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&amenities=POOL)

Apart hotel

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&lodging=APART_HOTEL)

Great for families

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&travelerType=family_friendly)

Spa

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&amenities=SPA_ON_SITE)

Hot tub

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&lodging=APARTMENT)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&lodging=COTTAGE)

Condo

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-04&d1=2026-03-04&endDate=2026-03-06&d2=2026-03-06&lodging=CONDO)

## Check prices for these dates

Tonight

[Feb 17 - Feb 18](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-02-17&endDate=2026-02-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 18 - Feb 19](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-02-18&endDate=2026-02-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Side hotels

![Traditional Room, 2 Queen Beds, Non Smoking | Premium bedding, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a.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)

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

### Carlton Inn Midway

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

Archer Heights

6.4/10

(1,005 reviews)

"It is a good place to stay."

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

Paul Adrian

$88 nightly

$104 total

Feb 19 - Feb 20

Total with taxes and fees

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403.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)

![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 | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/b932f6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

West Lawn

8.4/10

Very Good

(1,000 reviews)

"Staff very friendly "

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

Kali

$98 nightly

$113 total

Mar 17 - Mar 18

Total with taxes and fees

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

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/38fe6f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/6c3662e6.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.com/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information)

Garfield Ridge

4.6/10

(119 reviews)

"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."

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

Stephen

$85 nightly

$100 total

Feb 24 - Feb 25

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.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)

![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.com/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(2,377 reviews)

"Great stay"

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

Blake

$161 nightly

$189 total

Feb 24 - Feb 25

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/32b602ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freehand Chicago

[](https://www.expedia.com/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

Downtown Chicago

8.0/10

Very Good

(2,764 reviews)

"I enjoyed my stay"

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

Emily

$69 nightly

$82 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Freehand-Chicago.h9418281.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)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/68145d79.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)

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

### FOUND Hotel Chicago River North

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

Downtown Chicago

8.4/10

Very Good

(461 reviews)

"Amazing staff and very clean, modern rooms!"

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

genevieve

$61 nightly

$71 total

Feb 23 - Feb 24

Total with taxes and fees

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

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/11ef5a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fec06d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/d9163f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitehall Hotel, BW Premier Collection

[](https://www.expedia.com/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

Downtown Chicago

8.4/10

Very Good

(3,960 reviews)

"Great location, the room was nice and the breakfast was good. Overall great value for this property"

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

Jorge

$69 nightly

$81 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Whitehall-Hotel.h17903.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)

![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)

![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/33cb1dae.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.com/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(3,365 reviews)

"Amazing place, breakfast is great , location is great - honestly great hotel! "

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

Brisa

$123 nightly

$144 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/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)

![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.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)

### Aloft Chicago Mag Mile

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

Downtown Chicago

8.6/10

Excellent

(3,106 reviews)

"Great location and friendly staff. "

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

Pablo

$99 nightly

$116 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Indoor wedding](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/32068350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/aa950453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Swissotel - Chicago

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

Downtown Chicago

9.0/10

Wonderful

(3,201 reviews)

"Place is always top notch..stay here anytime we stay in Chicago."

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

Jon

$152 nightly

$178 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/c33b753e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/b5ce1c29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/79f898c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Grant Park Hotel

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

Downtown Chicago

8.2/10

Very Good

(2,673 reviews)

"Clean room and the staff are great. "

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

Doug

$67 nightly

$79 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Presidential Suite, 1 King Bed | Bathroom | Separate tub and shower, designer toiletries, hair dryer, bathrobes](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6bab11c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite, 1 Bedroom, 1 King Bed, 1 Sofabed | Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/b60fd014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/2f29850e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6b3ccd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sofitel Chicago Magnificent Mile

[](https://www.expedia.com/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(2,323 reviews)

"Staff was friendly and helpful! Great stay!"

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

Kristin

$211 nightly

$248 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.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)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.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)

![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.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

Downtown Chicago

8.0/10

Very Good

(9,906 reviews)

"Great location, beautiful historic hotel with clean, updated rooms. "

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

Jennifer

$87 nightly

$102 total

Feb 23 - Feb 24

Total with taxes and fees

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

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Lake View | Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h1497x0y3-3b277bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Chicago

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

Downtown Chicago

9.4/10

Exceptional

(3,479 reviews)

"Clean room, great staff, great location "

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

Tiffany

$190 nightly

$223 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/b675990c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, laptop workspace, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/1daf4199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business center](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/8fb5e606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/c26befab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Downtown Chicago

[](https://www.expedia.com/Chicago-Hotels-Travelodge-By-Wyndham-Downtown-Chicago.h196959.Hotel-Information)

Downtown Chicago

7.4/10

Good

(2,515 reviews)

"Always a good stay"

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

Domenic

$71 nightly

$84 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Travelodge-By-Wyndham-Downtown-Chicago.h196959.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)

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

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/54e0cfd7.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)

### The Chicago Hotel Collection Ambassador Gold Coast

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

Downtown Chicago

8.2/10

Very Good

(1,282 reviews)

"Great hotel with great location. Would definitely stay here again. "

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

Sheila

$95 nightly

$112 total

Feb 25 - Feb 26

Total with taxes and fees

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

![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar, cocktail bar](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/e039fcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite, 1 King Bed, Accessible | Living room | 55-inch LED TV with premium channels, TV, first-run movies](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/72c3363f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LondonHouse Chicago, Curio Collection by Hilton

[](https://www.expedia.com/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(3,588 reviews)

"Staff was friendly and loved the decor at this hotel…will definitely be staying again"

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

Osama

$183 nightly

$215 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

![Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/bc30a848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/160ef77b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom | In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/c17a5069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/ab59d7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sports Illustrated Resorts Chicago

[](https://www.expedia.com/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,399 reviews)

"Staff was super friendly and rooms were clean. Definitely will come back "

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

Daisy

$185 nightly

$217 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/60032ea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b59ebdf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/95d420ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pendry Chicago

[](https://www.expedia.com/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(1,150 reviews)

"Excellent hotel and location."

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

Marcelo

$225 nightly

$264 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Pendry-Chicago.h982552.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)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/b161c307.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)

### Staypineapple, An Iconic Hotel, The Loop

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

Downtown Chicago

9.4/10

Exceptional

(1,009 reviews)

"Location was great, staff was very friendly, and the rooms were clean. "

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

Lori

$155 nightly

$182 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Staypineapple.h284792.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.com/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05&regionId=553248635976475403&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=HTG_SPRING_PROMO_553248635976475403)

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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.com/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 acclaimed theater scene. 

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

### 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.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621555594769)

### 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.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=866963271656538112)

## Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side.

[See all hotels in Southwest Side](https://www.expedia.com/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05&adults=2&regionId=553248635976475403)

![Chicago, IL which includes landscape views and an airport](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

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Clean room, breakfast room staff friendly and efficient, check in and checkout fast. They accommodated my room location preferences and it was a quiet sleep. I like hard floors instead of carpet but the same vinyl flooring was used throughout which made the whole place feel like a hospital vs nice hotel."

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

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

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"The room was super clean with an amazing view and super conveniently located near the elevators. The staff was very friendly and got everything done that I needed! The amenities were also very nice, just with the pool was open. "

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

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

### Eurostars Magnificent Mile

10/10 Excellent

"Everything was very well put together! "

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

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg)

### theWit Chicago, a Hilton Hotel

10/10 Excellent

"Staff was really courteous and very helpful. The room was great, very clean and spacious with an awesome view. Overall really great hotel!!"

[](https://expedia.com/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information)

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg)

### Aloft Chicago Mag Mile

10/10 Excellent

"Every time we go to Chicago we stay here. Always a great stay "

[](https://expedia.com/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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

"."

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

"Yr"

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

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg)

### Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent

"Great hotel near all main attractions,friendly staff, great room at an affordable price. Will stay again."

[](https://expedia.com/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

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

### River Hotel

10/10 Excellent

"I really loved the location of this hotel. It was right in the city is walking distance to every hotspot in the downtown Chicago area ie. The Bean, Riverwalk, Skydeck etc. The room I had was basic with a kitchenette. There’s another hotel right next door if you want drinks/food for the evening. I would stay here again."

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

## More cheap stays in Southwest Side

![Motel 6 Naperville, IL](https://images.trvl-media.com/lodging/1000000/10000/9300/9225/4ecd9a2e_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

$47 nightly

$52 total

Feb 24 - Feb 25

Total with taxes and fees

7.8/10 Good! (1,239 reviews)

[](https://expedia.com/Chicago-Hotels-Motel-6-Naperville.h9225.Hotel-Information)

![Motel 6 Schiller Park, IL - Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/990000/983700/983642/4802495f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

$47 nightly

$53 total

Feb 22 - Feb 23

Total with taxes and fees

6.6/10 (1,987 reviews)

[](https://expedia.com/Chicago-Hotels-Motel-6-Schiller-Park.h983642.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

$67 nightly

$79 total

Mar 2 - Mar 3

Total with taxes and fees

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

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

![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/w3838h2556x2y3-00664b38_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$72 nightly

$80 total

Feb 19 - Feb 20

Total with taxes and fees

9/10 Wonderful! (2,566 reviews)

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

![Quality Inn O'Hare Airport](https://images.trvl-media.com/lodging/1000000/20000/12700/12621/8f09eb11_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

$71 nightly

$81 total

Mar 3 - Mar 4

Total with taxes and fees

7.6/10 Good! (1,957 reviews)

[](https://expedia.com/Chicago-Hotels-Quality-Inn-OHare-Airport.h12621.Hotel-Information)

![Sonesta Simply Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/330000/328600/328524/c5f12fbd_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Sonesta Simply Suites Chicago O'Hare Airport

4021 North Mannheim Rd Schiller Park IL

$76 nightly

$87 total

Feb 22 - Feb 23

Total with taxes and fees

8.2/10 Very Good! (2,375 reviews)

[](https://expedia.com/Chicago-Hotels-Sonesta-Simply-Suites-Chicago-OHare.h328524.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.com/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

151 properties

[](https://expedia.com/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

268 properties

[](https://expedia.com/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

381 properties

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

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- [3 Star Hotels in West Englewood ](https://www.expedia.com/3Star-West-Englewood-Chicago-Hotels.s30-n6132412-0.Travel-Guide-Filter-Hotels)
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- [Visit Gage Park ](https://www.expedia.com/Chicago-Gage-Park.dx6132375)
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- [Bridgeport Art Center ](https://www.expedia.com/Bridgeport-Art-Center-Bridgeport.d553248621533116324.Vacation-Attraction)
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- [Visit South Englewood ](https://www.expedia.com/Chicago-South-Englewood.dx6132433)
- [South Englewood Vacations ](https://www.expedia.com/South-Englewood.d6132433.Destination-Travel-Guides)

- [Car rentals near Chicago ](https://www.expedia.com/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)
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- [Enterprise Rental Cars in Midway Intl. ](https://www.expedia.com/Enterprise-Car-Rentals-In-Midway-Intl.d5719117-c15.Car-Rental-Guide-Suppliers)
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