Hotels with Entertainment in Southwest Side, IL

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Explore 36 Hotels with Entertainment in Southwest Side from $88

Carlton Inn Midway
Carlton Inn Midway
Hotel
Chicago, IL, USA
2.1k from Southwest Side center

Accommodations, Motels, Parking, Pet-friendly, Lodgings, Places to stay, Accessible hotels

5.0

Review score

832 reviews

$99
Average price / night
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Sleep Inn Midway Airport Bedford Park
Sleep Inn Midway Airport Bedford Park
Hotel
6650 S Cicero Ave, Chicago, IL, 60638, United States
4.0k from Southwest Side center

AC, Airport Transportation, Breakfast Included, Business Services, Crib, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping

8.0

Good

1821 reviews

$118
Average price / night
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Hampton Inn Chicago-Midway Airport
Hampton Inn Chicago-Midway Airport
Hotel
Chicago, IL, USA
3.9k from Southwest Side center

Accommodations, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.0

Good

394 reviews

$1105
Average price / night
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Chicago Marriott Midway
Chicago Marriott Midway
Hotel
6520 South Cicero Avenue, Chicago, IL, 60638, United States
4.0k from Southwest Side center

AC, Airport Transportation, Bar, Breakfast Available, Business Services, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping

8.4

Very Good

936 reviews

$189
Average price / night
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Hilton Garden Inn Chicago/Midway Airport
Hilton Garden Inn Chicago/Midway Airport
Hotel
Chicago, IL, USA
3.9k from Southwest Side center

Accommodations, Pools, Parking, Hilton , Pet-friendly, 3-star, Lodgings, Places to stay, Family

7.8

Good

243 reviews

$172
Average price / night
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Courtyard by Marriott Chicago Midway Airport
Courtyard by Marriott Chicago Midway Airport
Hotel
6610 S Cicero Ave, Chicago, IL, 60638, United States
4.1k from Southwest Side center

AC, Airport Transportation, Bar, Breakfast Available, Business Services, Elevator, Fitness Equipment, Frontdesk 24 Hour, Grocery

8.2

Very Good

1003 reviews

$173
Average price / night
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Courtyard Chicago Midway Airport
Courtyard Chicago Midway Airport
Hotel
Bedford Park, IL, USA
4.1k from Southwest Side center

Accommodations, Pools, Parking, Marriott , Pet-friendly, 3-star, Lodgings, Places to stay, Family

7.6

Good

233 reviews

$158
Average price / night
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Budget-Friendly King Room Perfect for a Relaxing Getaway near Soldier Field
Budget-Friendly King Room Perfect for a Relaxing Getaway near Soldier Field
Hotel
Cook County, IL, 60652, United States
5.5k from Southwest Side center

AC, Balcony, Free Parking, Heater, Internet, Microwave, No Smoking, TV

New to Booking
$88
Average price / night
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Affordable Stay Near Midway Airport – King-Size Comfort + Convenient Location
Affordable Stay Near Midway Airport – King-Size Comfort + Convenient Location
Hotel
Cook County, IL, 60652, United States
5.5k from Southwest Side center

AC, Balcony, Free Parking, Heater, Internet, Microwave, No Smoking, TV

New to Booking
$88
Average price / night
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Fairfield Inn & Suites Chicago Midway Airport
Fairfield Inn & Suites Chicago Midway Airport
Hotel
Bedford Park, IL, USA
4.1k from Southwest Side center

Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.3

Very Good

263 reviews

$149
Average price / night
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Sleep Inn Midway Airport
Sleep Inn Midway Airport
Hotel
Chicago, IL, USA
4.1k from Southwest Side center

B&bs, Accommodations, Parking, Inns, Pet-friendly, Lodgings, Places to stay, Accessible hotels

7.7

Good

733 reviews

$116
Average price / night
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DoubleTree by Hilton Chicago Midway Airport, IL
DoubleTree by Hilton Chicago Midway Airport, IL
Hotel
Bedford Park, IL, USA
4.2k from Southwest Side center

Accommodations, Pools, 4-star, Lodgings, Places to stay, Accessible hotels

8.5

Very Good

145 reviews

$197
Average price / night
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Hyatt Place Chicago Midway Airport
Hyatt Place Chicago Midway Airport
Hotel
Bedford Park, IL, USA
4.3k from Southwest Side center

Accommodations, Pools, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Family

8.6

Fabulous

809 reviews

$181
Average price / night
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SpringHill Suites by Marriott Chicago Chinatown
SpringHill Suites by Marriott Chicago Chinatown
Hotel
Chicago, IL, USA
8.6k from Southwest Side center

Cheap, Accommodations, Parking, 3-star, Lodgings, Places to stay, Family, Self-catering, Accessible hotels

9.0

Fabulous

658 reviews

$212
Average price / night
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Hampton Inn & Suites Bridgeview Chicago, Il
Hampton Inn & Suites Bridgeview Chicago, Il
Hotel
Southwest Side, Illinois, USA
8.8k from Southwest Side center

Cheap, Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.5

Very Good

507 reviews

$127
Average price / night
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Sophy Hyde Park
Sophy Hyde Park
Hotel
Southwest Side, Illinois, USA
9.2k from Southwest Side center

Luxury, Accommodations, Parking, Pet-friendly, 4-star, Lodgings, Places to stay, Family, Accessible hotels

9.1

Superb

220 reviews

$2333
Average price / night
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Hampton Inn Chicago McCormick Place
Hampton Inn Chicago McCormick Place
Hotel
Chicago, IL, USA
9.4k from Southwest Side center

Cheap, Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.4

Very Good

788 reviews

$184
Average price / night
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Hilton Garden Inn Chicago McCormick Place
Hilton Garden Inn Chicago McCormick Place
Hotel
Chicago, IL, USA
9.4k from Southwest Side center

Accommodations, Pools, Parking, Hilton , Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.0

Good

334 reviews

$161
Average price / night
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Home2 Suites By Hilton Chicago McCormick Place
Home2 Suites By Hilton Chicago McCormick Place
Hotel
Chicago, IL, USA
9.4k from Southwest Side center

Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.9

Fabulous

272 reviews

$258
Average price / night
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Hyatt House Chicago Medical/University District
Hyatt House Chicago Medical/University District
Hotel
Chicago, IL, USA
9.4k from Southwest Side center

Accommodations, Parking, Pet-friendly, 4-star, Lodgings, Places to stay, Accessible hotels

8.5

Very Good

953 reviews

$196
Average price / night
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Hyatt Place Chicago Medical/University District
Hyatt Place Chicago Medical/University District
Hotel
Chicago, IL, USA
9.4k from Southwest Side center

Accommodations, Parking, Pet-friendly, 4-star, Lodgings, Places to stay, Accessible hotels

8.4

Very Good

1534 reviews

$235
Average price / night
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Pro Tip for Travelers:
HotelsWithSuites simplifies your search by aggregating premium inventory from global leaders like Booking.com, Expedia, and Vrbo. Whether you need oceanfront hotels, a private pool, or a pet-friendly suite, use our Advanced Filters to instantly compare the top-rated Hotels with Entertainment in Southwest Side.

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Southwest Side Hotels with Entertainment on the Map

Frequently Asked Questions

Entertainment offerings may include live music, cultural shows, game rooms, or on-site events depending on the hotel’s category and facilities.

Some hotels include basic entertainment at no extra cost, while others may charge separately for premium shows or special events.

Hotels with entertainment in Southwest Side generally start from around $88 per night, depending on the level of facilities and activities offered.

Yes, many entertainment-focused hotels are designed for families and groups, offering activities suitable for both adults and children.

Along with entertainment options, many properties also offer Entertainment, Accessibility, and Security/Safety for a more complete stay experience.