Hillside Holiday Rentals, Chicago: Private House Rentals

A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Our top choices for Hillside hotels

A lobby with a reception desk, patterned sofas, a glass-top table with a potted plant, and a decorative mirror.

A gym with treadmills, elliptical machines, and weight equipment.

A hotel room with a bed, a television, a desk, a chair, and a patterned carpet.

A conference room with a wooden door, two black office chairs, a black desk with a computer and printer, and two monitors on the wall.

1. Best Western Plus Chicago Hillside

Hillside

Marquisha

฿3,341

฿3,741 total

includes taxes & fees

4 Oct - 5 Oct

A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.

A reception area with two reception desks, a wall-mounted display, and a carpeted floor.

A hotel room with a blue sofa, a wooden coffee table, a bed with white linens, a desk with a chair, and a window with curtains.

An indoor swimming pool with blue chairs and a tiled floor.

2. Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

Hillside

Nancy

฿3,978

฿4,454 total

includes taxes & fees

25 Oct - 26 Oct

A MainStay Suites hotel with a large sign, a parking lot, and a building in the background.

A living room with a sofa, a coffee table, a TV, and an air conditioner.

A hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.

A lobby with two leather armchairs, a small black table, a flat-screen TV on the wall, and a sign indicating a staff-only room.

3. MainStay Suites Chicago Hillside

Hillside

Pamela

฿2,671

฿2,991 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

4. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

฿4,769

฿5,484 total

includes taxes & fees

28 Sept - 29 Sept

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

5. Carleton of Oak Park

Oak Park

Suzanne

฿4,091

฿4,540 total

includes taxes & fees

28 Sept - 29 Sept

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.

A snack and beverage kiosk with various snacks and drinks.

6. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Michael

฿3,235

฿3,590 total

includes taxes & fees

4 Oct - 5 Oct

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

A modern living room with a sectional sofa, a fireplace, and a bar area.

A modern living room with a brown leather sofa, a coffee table, and a side table with a lamp.

An outdoor patio with a wooden table and wicker chairs, surrounded by blue umbrellas, and a building with large windows in the background.

7. Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

Ramona

฿4,813

฿5,545 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a microwave, a refrigerator, and a coffee machine.

A modern hotel corridor with wooden paneling, a staircase, and a snack bar with various packaged goods.

A hotel reception desk with two computer stations, a modern wall design, and a visible window.

A modern building with a large glass facade, a prominent circular structure on the right, and a landscaped entrance area.

8. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Des Plaines

Yashica Slater

฿4,379

฿5,166 total

includes taxes & fees

4 Oct - 5 Oct

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A modern bathroom with a dual sink vanity, a large mirror, and a toilet.

9. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

฿10,557

฿12,551 total

includes taxes & fees

14 Oct - 15 Oct

An indoor swimming pool with two separate sections, a brick wall, and a view of the outdoors through large windows.

A spacious restaurant with multiple tables and chairs, a brick wall, and a large window.

A hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, and a framed picture on the wall.

A lobby with a brick wall, a round mirror, a glass coffee table, and a reception desk.

10. Quality Inn Schaumburg - Chicago near the Mall

Schaumburg

Sommer

฿3,239

฿3,724 total

includes taxes & fees

25 Oct - 26 Oct

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

A view from a window with a cityscape in the background, including modern buildings and a clear sky.

A modern interior with a long counter, glass partitions, and a brick wall backdrop.

A modern lounge area with seating, a bar, and large windows offering views.

11. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

฿9,025

฿10,730 total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A gym with cardio machines, weight benches, and a large window offering a city view.

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

A modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

12. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Yassine

฿7,086

฿8,425 total

includes taxes & fees

25 Oct - 26 Oct

An outdoor seating area with sofas and tables, surrounded by greenery and modern buildings in the background.

A modern hotel room with a large window, a sofa, a small table, and a kitchen area with wine bottles.

A modern hotel lobby with multiple round tables, comfortable seating, a large window offering a city view, and a contemporary art piece on the wall.

A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

13. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Downtown Chicago

Brock

฿7,643

฿9,086 total

includes taxes & fees

25 Oct - 26 Oct

An indoor swimming pool with wooden beams, clear glass walls, and lounge chairs.

A hotel lobby with a dining area, a bar, and a seating area with curtains.

A hotel room with two single beds, a desk with a chair, a flat-screen TV mounted on the wall, and a window with curtains.

A hotel lobby with a marble reception desk, seating area, and a view of the outdoors.

14. Hampton Inn Chicago-Carol Stream

Carol Stream

Kristiane

฿3,426

฿3,802 total

includes taxes & fees

18 Oct - 19 Oct

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A bar area with a marble countertop, bar stools, and a variety of bottles.

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

15. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

฿6,822

฿9,063 total

includes taxes & fees

25 Oct - 26 Oct

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

An indoor swimming pool with lounge chairs and a no diving sign.

A modern hotel lobby with multiple dining areas, a central food station, and a high-ceiling atrium with balconies.

A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Melissa

฿6,876

฿9,155 total

includes taxes & fees

25 Oct - 26 Oct

A multi-story hotel with a prominent sign reading "Crowne Plaza."

A spacious lobby with a seating area, a reception desk, and a large screen.

A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.

A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

17. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Victoria

฿6,506

฿7,736 total

includes taxes & fees

27 Sept - 28 Sept

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

18. L7 Chicago by LOTTE

Downtown Chicago

GUILLERMO

฿8,637

฿10,268 total

includes taxes & fees

25 Oct - 26 Oct

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

19. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

฿6,052

฿7,195 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel with a glass facade, multiple floors, and a prominent sign.

A hotel reception desk with a marble counter, a digital kiosk, and a sign indicating Hilton Honors.

A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

A hotel pool area with a clear view of the cityscape through large windows, a pool with a metal ladder, and several lounge chairs.

20. Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

Rebecca

฿6,881

฿8,181 total

includes taxes & fees

27 Sept - 28 Sept

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Learn more about Hillside

This small village offers a peaceful escape with its charming Hillside Park and community events throughout the year. Grab a bite at local family restaurants before exploring nearby Forest Park's beautiful Concordia Cemetery or Oak Park's Frank Lloyd Wright attractions.

See all hotels in Hillside

A gravestone with the name Alphonse Capone, birth and death years, and the phrase "My Jesus Mercy".

Top Hillside Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"staff was super friendly and helpful!"

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Great location, close to the pink line, river is walkable distance, lots of restaurants etc. close parking if you don’t want to pay valet. Downside: no coffee in the room, they have it in the lobby but I like a good garbage coffee before I get dressed (Starbucks is attached as well if you want to pay for coffee). Second was many of the restaurants close on the weekend since it’s the business district."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"The room was very clean and spacious. Our check in was easy and the staff was very helpful with recommendations. Didn't make it for the breakfast but it sounded like it was good after meeting some other guest."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"L"

More cheap stays in Hillside

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,451

฿2,745 total

28 Sept - 29 Sept

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Naperville

1698 West Diehl Road Naperville IL

฿2,677

฿2,985 total

11 Oct - 12 Oct

includes taxes & fees

7.2/10 Good! (1,002 reviews)

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

฿3,006

฿3,456 total

20 Oct - 21 Oct

includes taxes & fees

7.2/10 Good! (1,008 reviews)

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

฿3,235

฿3,590 total

4 Oct - 5 Oct

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

฿5,615

฿6,676 total

25 Oct - 26 Oct

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿6,506

฿7,735 total

27 Sept - 28 Sept

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Hillside?

Located 14.3 mi (23 km) from the heart of Hillside, River Hotel is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Congress Plaza Hotel and The Chicago Hotel Collection Ambassador Gold Coast. See all available top hotels, or vacation rentals in Hillside.

If I need to cancel my hotel reservation in Hillside, will I receive a refund?

Yes! The majority of hotel reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillside.

What is the top LGBTQ-friendly accommodation in Hillside?

Best Western Plus Chicago Hillside is a top LGBTQ-friendly hotel that features free Wi-Fi and free parking. Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG and Manor Motel By OYO Near Oak Brook/Chicago Westchester are other good choices for your stay. See all available hotels listed as LGBTQ-friendly in Hillside.

What's the best dog-friendly place to stay in Hillside?

Best Western Plus Chicago Hillside is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. MainStay Suites Chicago Hillside is another option for you and your pet. See more pet-friendly hotel accommodations in Hillside.

What are some accommodation options with pools in Hillside?

Hilton Chicago: Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool and a health club. View all hotels with pools in Hillside.

What is staying in Hillside like?

Families will find child-friendly activities in Hillside, and visitors give high marks for the top-notch restaurants. Relaxing and welcoming, this city attracts tourists with its shopping and forests. Around the area, top sights include Wrigley Field, Soldier Field and Navy Pier. In Hillside, there are 5 hotels and other accommodation options to choose from. Find out more about Hillside.

What is there to see in Hillside?

Notable places to visit in the wider area include Wrigley Field, Soldier Field and Navy Pier. You'll also find United Center and Michigan Avenue in the area. Take a look at what more there is to see and do in Expedia's Hillside guide.

What's the seasonal weather like in Hillside?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.

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Book Hotels in Hillside on Expedia.com

Find hotels in Hillside, IL from ฿2,745

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Hillside

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Hillside hotels

1. Best Western Plus Chicago Hillside

2. Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

3. MainStay Suites Chicago Hillside

4. Hampton Inn Chicago-O'Hare International Airport

5. Carleton of Oak Park

6. SureStay Plus Hotel by Best Western Chicago Lombard

7. Holiday Inn Chicago O'Hare – Rosemont by IHG

8. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

9. Hilton Vacation Club Hotel Blake Chicago

10. Quality Inn Schaumburg - Chicago near the Mall

11. Hyatt House Chicago/West Loop-Fulton Market

12. Hyatt Place Chicago/Downtown - The Loop

13. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

14. Hampton Inn Chicago-Carol Stream

15. Hotel Riu Plaza Chicago

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

17. Crowne Plaza Chicago West Loop by IHG

18. L7 Chicago by LOTTE

19. Hilton Chicago/Magnificent Mile Suites

20. Hampton Inn Chicago West Loop Fulton Market Area

Learn more about Hillside

Top Hillside Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Allegro Royal Sonesta Hotel Chicago Loop

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

The Chicago Hotel Collection Ambassador Gold Coast

More cheap stays in Hillside

Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Naperville

Comfort Inn Chicago Schaumburg - O'Hare Airport

SureStay Plus Hotel by Best Western Chicago Lombard

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Frequently asked questions

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