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Southwest Side
Chicago
Illinois
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Find hotels in Southwest Side, IL from ฿1,085

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Check prices for these dates

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16 Jul - 17 Jul

Tomorrow

17 Jul - 18 Jul

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18 Jul - 20 Jul

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25 Jul - 27 Jul

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Top 10 Southwest Side hotels and places to stay

Enjoy a romantic breakfast on the balcony with a city view, surrounded by a selection of cheeses, fresh fruits, and nuts.

Relax in a stylish lounge area with a high ceiling, fireplace, and comfortable seating around a central coffee table.

Relax in our elegantly designed lobby, featuring a central seating area and grand staircase.

Relax in the elegant lobby, featuring a grand archway, fireplace, and comfortable seating areas.

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property

Downtown Chicago

8.2 out of 10, Very good, (1032)

8.2/10

Very good

(1032)

"Property was nice and a great location. Breakfast was good/convenient"

The price is ฿1,205

฿1,205

฿6,002 total

includes taxes & fees

27 Jul - 28 Jul

The Chicago Hotel Collection Ambassador Gold Coast

Claridge House

Relax in this stylish room with two single beds, a green armchair, and a flat-screen TV.

Enjoy cooking and dining in this kitchen with a central island, bar stools, and a large flat-screen TV.

Welcome to our elegant lobby, featuring a spacious reception area with a large entrance, comfortable seating, and a decorative pillar.

Claridge House

Claridge House

4.0 star property

Downtown Chicago

8.8 out of 10, Excellent, (1245)

8.8/10

Excellent

(1245)

"Comfy bed and linens, nice amenities and the staff checked on me via text throughout the stay. "

The price is ฿8,181

฿8,181

฿10,559 total

includes taxes & fees

17 Jul - 18 Jul

Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Relax in this stylish living room with a panoramic sea view, comfortable seating, and a sleek coffee table.

Enjoy a city view from the large window, with a round table and chair for relaxing.

Enjoy a drink at the bar, where a barista station serves up specialty beverages amidst a lively atmosphere with dining and socializing areas.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property

Downtown Chicago

9.4 out of 10, Exceptional, (2071)

9.4/10

Exceptional

(2071)

"Amazing property clean comfy bedding and wonderful views"

The price is ฿7,450

฿7,450

฿9,691 total

includes taxes & fees

27 Jul - 28 Jul

Sable at Navy Pier Chicago, Curio Collection by Hilton

Relax in a serene bedroom with a large bed, minimalist decor, and a cityscape painting above.

Kitchen area features a dishwasher, trash bin, and a potted plant on the countertop.

Cozy retreat with a compact kitchenette, microwave, and toaster, perfect for a relaxing stay.

Enjoy cooking in this functional kitchen with a central island and dining area.

Rainbow Motel

Rainbow Motel

Garfield Ridge

7.6 out of 10, Good, (4)

7.6/10

Good

(4)

"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 "

The price is ฿2,914

฿2,914

฿3,421 total

includes taxes & fees

21 Jul - 22 Jul

Enjoy a self-service breakfast with a variety of options at this well-equipped breakfast bar.

Welcome to our reception area, featuring a comfortable waiting space with a sofa and coffee table.

Enjoy a comfortable stay with two single beds, a flat-screen TV, and a desk for work or relaxation.

Relax in style with a spacious living room featuring a grey sectional sofa, a comfortable armchair, and a cozy reading nook.

Carlton Inn Midway

Carlton Inn Midway

2.0 star property

Archer Heights

6.6 out of 10, (1001)

6.6/10

(1001)

"The female clerk was very friendly and helpful!"

The price is ฿3,412

฿3,412

฿4,005 total

includes taxes & fees

29 Jul - 30 Jul

Carlton Inn Midway

Skylark Motel's exterior features a prominent sign with its name displayed in bold letters.

Comfortable retreat with a bed, desk, and TV, perfect for a restful stay.

Enter a welcoming space with a reception desk and a sign that reads 'WATCH YOUR STEP'.

Cozy retreat with a kitchenette featuring a microwave and refrigerator, plus a comfortable bed with a floral-patterned bedspread.

Skylark Motel

Skylark Motel

2.0 star property

Garfield Ridge

4.8 out of 10, (112)

4.8/10

(112)

"Poorly cleaned and not kept up well."

The price is ฿3,551

฿3,551

฿4,169 total

includes taxes & fees

17 Jul - 18 Jul

Relax in style with plush seating and a classic design, featuring a sofa, armchairs, and a bookshelf.

Welcome to our reception area, featuring a stylish counter and pendant lights above, a shelf with decorative items, and a window with a view of the street.

Book lovers can enjoy a curated collection of art and literature on display.

Step into a welcoming space with a bar area featuring a selection of beverages and lush greenery.

Freehand Chicago

Freehand Chicago

4.0 star property

Downtown Chicago

8.0 out of 10, Very good, (2079)

8.0/10

Very good

(2079)

"Stayed many times, great fun!"

The price is ฿3,636

฿3,636

฿4,842 total

includes taxes & fees

6 Aug - 7 Aug

Freehand Chicago

Experience the vibrant city atmosphere from this unique, circular building with a glass facade offering a glimpse into the interior.

Relax in our spacious seating area with comfortable sofas and chairs, surrounded by a stylish bar and large window.

Relax in a serene urban setting with a spacious seating area and unobstructed city views.

Relax in the stylish lobby with a herringbone-patterned wall, dark leather sofa, and comfortable seating area.

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4.0 star property

Downtown Chicago

7.2 out of 10, Good, (1096)

7.2/10

Good

(1096)

"Great stay"

The price is ฿1,085

฿1,085

฿5,861 total

includes taxes & fees

27 Jul - 28 Jul

The Chicago Hotel Collection - Magnificent Mile

Enjoy a casual dining experience with comfortable seating and a variety of beverages.

Relax in a stylish room with a large bed, city views, and a round table with a lamp.

Experience the warm and inviting lobby, featuring a central fireplace, comfortable seating, and a mix of modern and classic furnishings.

Relax by the rooftop pool with a stunning city view, surrounded by comfortable lounge chairs and a small table.

The Hoxton Chicago

The Hoxton Chicago

4.0 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1000)

9.0/10

Wonderful

(1000)

"Excellent location and great vibe. "

The price is ฿6,809

฿6,809

฿7,993 total

includes taxes & fees

10 Aug - 11 Aug

The Hoxton Chicago

Experience the vibrant atmosphere of this historic building, featuring ornate details and a lively dining and entertainment area.

Cozy retreat with a bunk bed design, featuring a neatly made bed and a window for natural light.

Experience the warm and inviting atmosphere of our lobby, featuring a central seating area with a long table and chairs, a blackboard, and a potted plant.

Contemporary space with a statement brick wall, wooden table, and eclectic decor.

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property

Downtown Chicago

8.0 out of 10, Very good, (128)

8.0/10

Very good

(128)

"Good hotel "

The price is ฿3,993

฿3,993

฿4,687 total

includes taxes & fees

6 Aug - 7 Aug

FOUND Hotel Chicago River North

Enjoy a casual coffee break in our cozy coffee shop with a menu board, seating area, and unique decor.

Welcome to the reception area, where friendly staff are available to assist with your stay. The space features a comfortable seating area and a convenient directory display.

Compact hotel room with a bunk bed, kitchenette, and small dining area.

Relax in this stylish room with a high ceiling, exposed beams, and a city view.

The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3.0 star property

Downtown Chicago

7.2 out of 10, Good, (517)

7.2/10

Good

(517)

"The rooms were excellent"

The price is ฿2,478

฿2,478

฿5,583 total

includes taxes & fees

23 Jul - 24 Jul

The Chicago Hotel Collection River North

Relax in the hotel lobby's spacious seating area, surrounded by a city view and comfortable sofas and armchairs.

Stylish building with a striking red accent, set in the heart of the city.

Two single beds with brown headboards, a desk and chair, and a television on a stand, offer a comfortable space to rest and unwind with a city view.

Relax in a stylish public area with a sleek reception counter, coffee machines, and a touch of greenery.

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2.0 star property

Downtown Chicago

7.2 out of 10, Good, (2227)

7.2/10

Good

(2227)

"Best Travelodge I have stayed at "

The price is ฿4,017

฿4,017

฿4,716 total

includes taxes & fees

4 Aug - 5 Aug

Travelodge by Wyndham Downtown Chicago

Relax in a casual, urban setting with seating areas and a prominent counter for ordering.

Enjoy a fully stocked kitchen with a refrigerator, condiments, and cereal.

Relax in our spacious lobby, featuring a central seating area with armchairs and sofas, a large flat-screen TV, and a decorative water feature.

Relax in this stylish seating area with four comfortable armchairs and a central coffee table, offering a view of the street outside.

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1269)

9.0/10

Wonderful

(1269)

"Great location and hotel "

The price is ฿5,056

฿5,056

฿5,936 total

includes taxes & fees

10 Aug - 11 Aug

Crowne Plaza Chicago West Loop by IHG

Stairs lead to a bar area with a counter and seating on the upper level.

Relax in style with a comfortable seating area, flat-screen TV, and a large window offering a view.

Stairs lead to an upper level, surrounded by geometric patterns and modern lighting.

Relax in a stylish lounge with a panoramic city view, plush seating, and a curved ceiling.

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1163)

9.0/10

Wonderful

(1163)

"Great location and property!"

The price is ฿4,509

฿4,509

฿6,254 total

includes taxes & fees

10 Aug - 11 Aug

Thompson Chicago, by Hyatt

Contemporary lounge area with a striking metal structure and large windows offering urban views.

Stunning historic building with a classic facade, featuring a large dome and evenly spaced windows.

Relax in our lounge area, featuring a bar, communal seating, and individual tables.

Relax in this stylish living room with a sofa, coffee table, and flat-screen TV, offering a view of the city skyline.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property

Downtown Chicago

9.4 out of 10, Exceptional, (3327)

9.4/10

Exceptional

(3327)

"Great stay"

The price is ฿5,483

฿5,483

฿6,437 total

includes taxes & fees

10 Aug - 11 Aug

LondonHouse Chicago, Curio Collection by Hilton

Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

Relax in a warm and inviting space with a comfortable sofa, armchair, and dining area.

Meetings are made easy in this well-equipped conference room with a long table, comfortable seating, and a large screen.

Relax in a cozy retreat with a large bed, tufted headboard, and a nightstand with a lamp.

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4.0 star property

Downtown Chicago

8.6 out of 10, Excellent, (1872)

8.6/10

Excellent

(1872)

"Great location near bars and restaurants "

The price is ฿4,138

฿4,138

฿5,622 total

includes taxes & fees

13 Aug - 14 Aug

Millennium Knickerbocker Chicago

Hotel facade with a balcony featuring a variety of flowers and large windows with metal railings.

Relax in the inviting lobby, featuring a fireplace, comfortable seating, and artwork on the walls.

Stunning staircase with a classic design, featuring a handrail and steps, leading to a contemporary space with a chandelier and flat-screen TV.

Indulge in a diverse spread of international cuisine at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property

Downtown Chicago

8.4 out of 10, Very good, (1000)

8.4/10

Very good

(1000)

"Excellent area of Chicago with dining and shopping "

The price is ฿4,535

฿4,535

฿5,323 total

includes taxes & fees

10 Aug - 11 Aug

Holiday Inn Express Chicago - Magnificent Mile by IHG

Relax in a stylish seating area with plush armchairs and a decorative partition, surrounded by ambient lighting and a patterned rug.

Two single beds with white linens and dark wood headboard, flat-screen TV, and a desk with chair.

Enjoy dining in a welcoming space with a long counter, comfortable seating, and decorative touches.

Welcome to our reception area, featuring a marble reception desk, traditional vases, and a motivational quote in gold.

Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 star property

Downtown Chicago

8.2 out of 10, Very good, (2548)

8.2/10

Very good

(2548)

"Location was excellent."

The price is ฿4,680

฿4,680

฿5,494 total

includes taxes & fees

12 Aug - 13 Aug

Best Western Grant Park Hotel

Experience the vibrant city atmosphere in this urban oasis, featuring a striking geometric-patterned awning and modern architecture.

Contemporary space with a central counter, display case, and hanging plant arrangement.

Stylish high-rise building in a vibrant urban setting.

Enjoy a city view from the large window in this stylish room with a comfortable bed and modern decor.

citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property

Downtown Chicago

9.4 out of 10, Exceptional, (3369)

9.4/10

Exceptional

(3369)

"Great location- fun hotel"

The price is ฿5,510

฿5,510

฿6,469 total

includes taxes & fees

4 Aug - 5 Aug

citizenM Chicago Downtown

Relax in the hotel lobby, featuring a spacious seating area with a sofa, armchairs, and a small table.

Relax in a spacious room with a large bed, desk, and comfortable armchair.

Experience a stylish and functional lobby with a curved ceiling, textured wall, and comfortable seating area.

Experience the grandeur of this historic hotel, featuring an arched entrance and a striking dome.

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4.0 star property

Downtown Chicago

8.2 out of 10, Very good, (1875)

8.2/10

Very good

(1875)

"Great location "

The price is ฿8,661

฿8,661

฿11,162 total

includes taxes & fees

26 Jul - 27 Jul

Hotel Felix River North/Magnificent Mile

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.

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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Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and S.S. Peter and Paul Church as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side

More cheap stays in Southwest Side

More cheap stays in Southwest Side

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street, Lombard, IL

The price is ฿3,652 per night from 5 Aug to 6 Aug

฿3,652

฿4,053 total

5 Aug - 6 Aug

includes taxes & fees

8.8/10 Excellent! (2,114 reviews)

SureStay Plus Hotel by Best Western Chicago Lombard

Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road, Naperville, IL

The price is ฿1,850 per night from 11 Aug to 12 Aug

฿1,850

฿2,063 total

11 Aug - 12 Aug

includes taxes & fees

7.8/10 Good! (1,020 reviews)

Motel 6 Naperville, IL

Quality Inn O'Hare Airport

Quality Inn O'Hare Airport

3801 North Mannheim Road, Schiller Park, IL

The price is ฿2,610 per night from 5 Aug to 6 Aug

฿2,610

฿2,974 total

5 Aug - 6 Aug

includes taxes & fees

7.4/10 Good! (1,398 reviews)

Quality Inn O'Hare Airport

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

65 E Harrison St, Chicago, IL

The price is ฿4,017 per night from 4 Aug to 5 Aug

฿4,017

฿4,716 total

4 Aug - 5 Aug

includes taxes & fees

7/10 Good! (2,235 reviews)

Travelodge by Wyndham Downtown Chicago

Best Western Grant Park Hotel

Best Western Grant Park Hotel

1100 S Michigan Ave, Chicago, IL

The price is ฿4,680 per night from 12 Aug to 13 Aug

฿4,680

฿5,494 total

12 Aug - 13 Aug

includes taxes & fees

8/10 Very Good! (2,561 reviews)

Best Western Grant Park Hotel

Best Western River North Hotel

Best Western River North Hotel

125 W Ohio St, Chicago, IL

The price is ฿4,680 per night from 27 Jul to 28 Jul

฿4,680

฿5,494 total

27 Jul - 28 Jul

includes taxes & fees

7.6/10 Good! (1,014 reviews)

Best Western River North Hotel

Accommodation near Southwest Side attractions

Accommodation near Southwest Side attractions

Top Southwest Side Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"I stayed at this 9"

derek 3-night trip

Posted 13 hours ago

Hilton Chicago/Magnificent Mile Suites

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Our room was clean and comfortable, and the staff was helpful. The complementary breakfast is well run with many food options. We appreciated how close it is to local attractions."

Blithe 2-night trip

Posted 21 hours ago

Embassy Suites by Hilton Chicago Downtown River North

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Great location on a quiet street close to water tower downtown. Parking across the street for a reasonable price. Huge room, comfortable beds and great staff. Breakfast was good also!"

Heidi 4-night trip

Posted 2 days ago

The Whitehall Hotel, BW Premier Collection

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"Great location, very centralized area near West loop. Easy check in and amenities available. Room was very clean and no issues. Would def recommend!"

briana 3-night trip

Posted 2 days ago

Crowne Plaza Chicago West Loop by IHG

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

10/10 Excellent

"Location was great - so many things (food, shopping, dining, sightseeing) in walking distance! And the staff was wonderful."

Sunu 3-night trip

Posted 2 days ago

The Westin Michigan Avenue Chicago

The Wade

The Wade

10/10 Excellent

"We had a beautiful view of lake Michigan and the room had modern updates that gave it a cool ambience. "

Jackie 1-night trip

Posted 3 days ago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Areas of Southwest Side

Hotels in Lower West Side
Hotels in Bridgeport
Hotels in Bedford Park
Hotels in Clearing
Hotels in Back of the Yards
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Hotels in Washington Park
Hotels in McKinley Park
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Hotels in Englewood
Hotels in New City
Hotels in Heart of Chicago
Hotels in Fuller Park
Hotels in Chicago Lawn
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Hotels in Ashburn

Accommodation near Southwest Side attractions

Hotels near Wrigley Field
Hotels near Navy Pier
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Hotels near Northwestern University

Hotels Near Southwest Side, Chicago

Rosemont Hotels
Naperville Hotels
Oak Brook Hotels
Evanston Hotels
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Joliet Hotels
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Downers Grove Hotels
Hammond Hotels
Schiller Park Hotels
Gary Hotels
Des Plaines Hotels
Oak Park Hotels
Bolingbrook Hotels
Glenview Hotels
Orland Park Hotels

Explore more hotels

The Westin Michigan Avenue Chicago
The Wade
Hyatt Regency Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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