Northwest Side Holiday Rentals, Chicago: Private House Rentals

A curved pathway with a metal fence, flowering trees, and a street lamp.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Northwest Side

Pet friendly

Apartment

Apart hotel

Pool

Condo

Spa

Hot tub

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Northwest Side hotels

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

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

A hotel room with a large bed, a desk with a chair, a sofa, and a TV.

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

1. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

LISA

4.421.378 ₫

5.256.575 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

2. Hotel Riu Plaza Chicago

Downtown Chicago

Peter

4.693.780 ₫

6.326.053 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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 hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

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

3. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Terrie

3.847.122 ₫

4.573.844 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.

Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

4. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

MAGALY

3.751.707 ₫

4.460.405 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A spacious lobby with a central coffee table, sofas, and a large mirror.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

5. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Dylan

3.498.894 ₫

4.159.834 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

6. L7 Chicago by LOTTE

Downtown Chicago

Girivasan

5.627.446 ₫

6.690.470 ₫ total

includes taxes & fees

30 Aug - 31 Aug

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

A grilled pineapple on top of a stack of meat, served on a pan.

A conference room with a long table, chairs, and a projector screen.

7. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

4.365.979 ₫

5.843.679 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A conference room with a long table, chairs, and a vase.

A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.

A man in a suit sitting by a window with a vase of red flowers.

8. River Hotel

Downtown Chicago

Patti

3.790.089 ₫

4.506.038 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A tall, modern hotel with a brick facade and numerous windows.

A modern hotel lobby with grey upholstered chairs, a wooden coffee table, and a large window offering a view of the city and an American flag.

9. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Sally

4.095.146 ₫

4.868.719 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

A modern high-rise building with a glass facade, surrounded by other tall buildings.

10. The Royal Sonesta Chicago River North

Downtown Chicago

Jennifer Lynn

5.197.283 ₫

7.015.158 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

A hotel room with a large bed, two bedside lamps, and a city view through a large window.

A modern living room with a large window, a potted plant, and a variety of seating options including a sofa, armchairs, and ottoman.

A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

11. Hyatt Place Chicago/River North

Downtown Chicago

Shoma

4.447.540 ₫

5.287.679 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

A swimming pool with a glass wall, a seating area with sofas, and an exit sign.

A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

12. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Hugo

3.974.224 ₫

4.724.953 ₫ total

includes taxes & fees

1 Sept - 2 Sept

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

13. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Ashraf

4.550.095 ₫

6.311.844 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

A multi-story hotel with a prominent sign reading 'CROWNE PLAZA' at the top.

14. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Jamie

4.506.488 ₫

5.358.078 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A modern building with a colorful facade and a red circular seating area.

A modern bar area with a checkered floor, wooden ceiling, and various bar equipment.

A modern interior with wooden shelves, colorful chairs, and hanging plants.

A modern hotel room with a large window offering a city view, a contemporary light fixture, and a clean, minimalist design.

15. citizenM Chicago Downtown

Downtown Chicago

lakadria

4.447.540 ₫

5.287.682 ₫ total

includes taxes & fees

7 Sept - 8 Sept

An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.

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

A spacious lobby with a high ceiling, modern seating, and a central bar area.

16. Holiday Inn Chicago Dwtn - The Mart by IHG

Downtown Chicago

Victor

5.040.581 ₫

6.769.205 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

A modern reception desk with a sleek design, large windows offering a view of the cityscape, and a contemporary ceiling with linear wood paneling.

A bar area with a long counter, bar stools, and a bar stocked with bottles.

A hotel room with two beds, a desk, a chair, a lamp, and a view of a building through the window.

17. Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

Claudia

4.839.970 ₫

5.754.241 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

A hotel room with a large window, a bed, a sofa, a desk, and a TV.

A modern bar area with a central counter, multiple seating tables, and a large window offering a view.

A hotel lobby with a reception desk, seating area, and a mural of a city skyline.

18. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Shilpa

3.737.343 ₫

4.908.994 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A modern dining area with round tables and chairs, large windows, and a view of a cityscape.

A modern high-rise building with a curved glass facade, surrounded by other tall buildings.

A person in a white robe sitting by a window with a view of modern high-rise buildings.

A hotel room with a large bed, a chair, a window with a city view, and a bathroom area with a toilet and a sink.

19. Sofitel Chicago Magnificent Mile

Downtown Chicago

Anton

6.775.958 ₫

8.833.733 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A spacious lobby with a grand staircase, a large abstract painting, and a seating area with modern furniture.

A spacious hotel lobby with a bar area, dining tables, and a central seating area.

A hotel with a classic facade, multiple flags, and a prominent entrance.

20. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Anthony

5.310.886 ₫

7.151.296 ₫ total

includes taxes & fees

7 Sept - 8 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Northwest Side attractions

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

See properties

Walt Disney House

Learn about the local history of Chicago with a stop at Walt Disney House. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

See properties

Six Corners

You can browse for the perfect souvenirs at Six Corners during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

See properties

Avondale Music Hall

You can make plans for a show at Avondale Music Hall on your trip to Chicago. Take in the live music while you're in the area.

See properties

Irish American Heritage Center

You can spend an afternoon exploring the galleries in Irish American Heritage Center in Chicago. Take in the live music while you're in the area.

See properties

The Gift Theatre

You can make plans for a show at The Gift Theatre during your stay in Chicago. Discover the top-notch restaurants and acclaimed theatre scene in this vibrant area.

See properties

Hanson Park

After visiting Hanson Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

See properties

COLOR CLUB

COLOR CLUB is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music while you're in the area.

See properties

Learn more about Northwest Side

Check out the local area in Northwest Side—home to attractions like Walt Disney House and Milwaukee Avenue.

See all hotels in Northwest Side

Top Northwest Side Hotel Reviews

Hyatt Regency O'Hare Chicago

10/10 Excellent

"Clean room, comfortable. Good coffee shop option."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Good place to stay"

Hilton Chicago

10/10 Excellent

"This was a clean stay! The staff members were pleasant. The location of the hotel was next to a lot of great tourist spots. The building is an older building but extremely clean and convenient. A big perk was that the Hop On Hop off bus was right outside the front door. I would stay at this location again."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"Everything was great! Staff was very accommodating 🙂"

The Royal Sonesta Chicago Downtown

8/10 Good

"Our second stay at the Royal Sonesta, and once again, we had a wonderful experience! The location is perfect for shopping, dining, and all the tourist attractions. Ubers were easy to get at any time of day or night, which made getting around so convenient although lots is within walking distance. The staff was friendly and welcoming, and we really enjoyed having the on-site bar and restaurant for a quick bite or a drink before heading out. Housekeeping did tidy our room each day. My only complaint was that one of the channels we watch frequently was glitching throughout our stay. We didn’t report it during our visit since we weren’t planning to spend much time in the room anyway. Overall, we had another great stay and would definitely recommend the Royal Sonesta! ⭐️"

Hotel Riu Plaza Chicago

10/10 Excellent

"❤️"

Crowne Plaza Chicago West Loop by IHG

8/10 Good

"Loved our stay"

The Wade

10/10 Excellent

"Good stay, great location"

More cheap stays in Northwest Side

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

1.493.631 ₫

1.665.099 ₫ total

13 Sept - 14 Sept

includes taxes & fees

7.8/10 Good! (1,462 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

1.642.759 ₫

1.839.561 ₫ total

2 Sept - 3 Sept

includes taxes & fees

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

2.305.348 ₫

2.650.690 ₫ total

10 Sept - 11 Sept

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

3.008.678 ₫

3.576.984 ₫ total

30 Aug - 31 Aug

includes taxes & fees

7.6/10 Good! (2,781 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

2.977.338 ₫

3.756.266 ₫ total

8 Sept - 9 Sept

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

3.862.704 ₫

4.592.370 ₫ total

9 Sept - 10 Sept

includes taxes & fees

8/10 Very good! (1,532 reviews)

Explore a world of travel with Expedia

Book Hotels in Northwest Side on Expedia.com

Find hotels in Northwest Side, IL from 1.665.099 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Northwest Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Northwest Side hotels

1. Hyatt Place Chicago/Downtown - The Loop

2. Hotel Riu Plaza Chicago

3. Hilton Chicago/Magnificent Mile Suites

4. DoubleTree by Hilton Chicago - Magnificent Mile

5. The Chicago Hotel Collection Ambassador Gold Coast

6. L7 Chicago by LOTTE

7. Hyatt Centric The Loop Chicago

8. River Hotel

9. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10. The Royal Sonesta Chicago River North

11. Hyatt Place Chicago/River North

12. Embassy Suites by Hilton Chicago Downtown River North

13. Sable at Navy Pier Chicago, Curio Collection by Hilton

14. Crowne Plaza Chicago West Loop by IHG

15. citizenM Chicago Downtown

16. Holiday Inn Chicago Dwtn - The Mart by IHG

17. Springhill Suites by Marriott Chicago Downtown/ River North

18. La Quinta Inn & Suites by Wyndham Chicago Downtown

19. Sofitel Chicago Magnificent Mile

20. The Allegro Royal Sonesta Hotel Chicago Loop

Stay near popular Northwest Side attractions

Portage Park

Walt Disney House

Six Corners

Avondale Music Hall

Irish American Heritage Center

The Gift Theatre

Hanson Park

COLOR CLUB

Learn more about Northwest Side

Top Northwest Side Hotel Reviews

Hyatt Regency O'Hare Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago

Club Quarters Hotel, Central Loop, Chicago

The Royal Sonesta Chicago Downtown

Hotel Riu Plaza Chicago

Crowne Plaza Chicago West Loop by IHG

The Wade

More cheap stays in Northwest Side

Motel 6 Naperville, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Comfort Inn Chicago Schaumburg - O'Hare Airport

Travelodge by Wyndham Downtown Chicago

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Explore a world of travel with Expedia

Go further with the Expedia app