North Side Holiday Rentals, Chicago: Private House Rentals

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Our top choices for North Side hotels

An outdoor patio area with brick flooring, outdoor seating, and potted plants.

A spacious living room with a fireplace, a staircase, and a bookshelf.

A modern hotel room with a desk, chair, and a dining area with a table and chairs.

A modern kitchen with dark cabinets, a microwave, and a coffee maker. There is a dining area with a table and chairs, and a sofa with cushions.

1. Best Western Plus Hawthorne Terrace Hotel

Lakeview

Barbara

฿7,698

฿9,037 total

includes taxes & fees

2 Nov - 3 Nov

A bar area with multiple seating options, including bar stools and round tables, with a variety of bottles and glasses on the bar counter.

An outdoor seating area with tables and chairs, potted plants, and a TV screen.

A modern interior with a brick wall, a staircase, and a large framed artwork.

A spacious room with a large window overlooking Wrigley Field, a view of the Chicago Cubs stadium, and a chessboard on the table.

2. Hotel Zachary Chicago, a Tribute Portfolio Hotel

Lakeview

Jeffrey

฿9,517

฿11,172 total

includes taxes & fees

1 Nov - 2 Nov

A modern lobby with a wooden floor, a staircase with glass railings, and a seating area with leather sofas.

A serene hallway with a Buddha statue, a stone bench, and a wall with a unique light pattern.

A hotel with a swimming pool, outdoor seating, and a view of the city skyline.

A modern hotel room with a marble bathroom, a large mirror, a bedside table, and a bed with a city view.

3. The Hotel at Midtown

Bucktown

Robert

฿7,699

฿10,818 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk, a television, and a window with a view of buildings.

A lobby with a reception desk, a green counter, a bar area, and a seating area with leather chairs.

The Willows Hotel with a classical facade, arched windows, and a signboard.

A well-appointed lounge area with a fireplace, leather armchairs, and a checkered floor.

4. The Willows Hotel

Lakeview

John S

฿4,039

฿4,742 total

includes taxes & fees

1 Nov - 2 Nov

A multi-story building with a brick facade, a well-maintained lawn, and a black metal fence.

A bar area with a dark blue brick wall, wooden slats, and a counter with two chairs.

A cozy lounge area with leather sofas, a central coffee table, and a fireplace.

A staircase with red carpet, wooden paneling on the walls, and a bar area with stools.

5. The Majestic Hotel

Lakeview

Michael

฿5,126

฿6,018 total

includes taxes & fees

1 Nov - 2 Nov

A rooftop lounge with a fire feature, seating, and a city view.

A staircase with a red wall adorned with various framed artworks.

A hotel lobby with a reception desk, leather seating, a patterned rug, and a wall with various artworks.

The entrance of Hotel Lincoln with a clear sign above the doors and a cyclist passing by.

6. Hotel Lincoln

Lincoln Park

Daniel

฿4,985

฿6,726 total

includes taxes & fees

25 Oct - 26 Oct

A hallway with a bench, a door, and a wall-mounted light fixture.

A kitchen with a microwave, coffee makers, and a shelf with glassware and dishes.

A dining area with a fireplace, a wooden table, and chairs. There is a kitchen area with cabinets and appliances.

A modern living room with a dining area, large windows, and a unique ceiling light fixture.

7. City Suites Hotel

Lakeview

Joel

฿4,814

฿5,651 total

includes taxes & fees

28 Oct - 29 Oct

The exterior of the Hotel Versey with a black awning, a glass entrance door, and potted plants with red and white flowers.

A hotel entrance with a sign reading 'HOTEL Verssey,' potted plants, and a clean sidewalk.

A hotel room with a large bed, a chair, a nightstand, and a wall with a Chicago Cubs mural.

A hotel corridor with a blue carpet, a colorful ceiling light fixture, and walls with motivational phrases like "STAY LIKE A LOCAL".

8. Hotel Versey Chicago Lincoln Park

Lakeview

Stephen

฿3,942

฿4,628 total

includes taxes & fees

2 Nov - 3 Nov

A bathroom with a glass-tiled wall, a sink, and a shower area.

A building with a large window, a bench, and a sign that reads "RAY'S BUCKTOWN BED & BREAKFAST".

A patio with a grill, outdoor seating, and potted plants.

A room with wooden flooring, a bookshelf filled with books and decorative items, two chairs, and a table with various objects.

9. Ray's Bucktown B&B

Bucktown

Lora

฿6,571

฿7,418 total

includes taxes & fees

13 Oct - 14 Oct

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

A bedroom with a bed, pillows, a painting, wall-mounted candelabras, and a window with curtains.

A modern kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a glass dining table with chairs.

A living room with a black patterned rug, a glass coffee table, a wooden dining table with chairs, a small bench, and a cityscape painting on the wall.

10. Dorothy's

Lakeview

Steven

฿1,365

฿2,779 total

includes taxes & fees

2 Nov - 3 Nov

A grand foyer with a wooden staircase, a chandelier, and a large window.

A courtyard with brick arches, outdoor seating, and potted plants.

A stone entrance with a black metal gate, a black mat, and two lion statues.

A spacious dining area with a long wooden table, ornate chairs, and a chandelier.

11. Villa D' Citta

Lincoln Park

Jeffrey

฿8,466

฿9,939 total

includes taxes & fees

2 Nov - 3 Nov

A staircase with white railings and a chandelier.

A corner room with a staircase, a fireplace, and large windows.

A modern bedroom with a bed, bedside tables, and a nightstand. There is a living area with a sofa and a coffee table. The room has large windows and a ceiling light.

A living room with a fireplace, a sofa, a staircase, and a door.

12. The Den Hotel

Lakeview

David

฿3,933

฿4,617 total

includes taxes & fees

12 Oct - 13 Oct

A hotel room with a wooden wardrobe, a small round table with chairs, and a patterned floor.

A rooftop patio with wicker furniture, a round table, and potted plants.

A cozy bar area with a wooden counter, cushioned seating, and a brick wall backdrop.

A modern interior with a sofa, a coffee table, and a wall of wine bottles.

13. The Chicago Hotel Collection - Wrigleyville

Lakeview

Rob

฿4,975

฿5,840 total

includes taxes & fees

25 Oct - 26 Oct

A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

A staircase with a wooden handrail and a mirror above it.

A narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

A narrow brick alley with a tree in the center, surrounded by potted plants and greenery.

14. The Villa Toscana

Lakeview

John

฿1,913

฿3,591 total

includes taxes & fees

2 Nov - 3 Nov

A buffet table with various food items including fruits, waffles, and condiments.

A cozy living room with a brick wall, wooden floor, and a sectional sofa.

A hallway with a sign for Wrigley Hostel Chicago, including address and contact information.

A row of brick townhouses with large windows and a central entrance.

15. Wrigley Hostel

Lakeview

Shelly

฿3,362

฿3,946 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

A covered outdoor seating area with a wooden deck, black metal chairs, and a glass table.

A living room with a television, a sofa, a chair, and a coffee table. There are windows and a clock on the wall.

A modern kitchen with dark wood flooring, stainless steel appliances, and a large island with a glass top.

16. Wrigleyville Suites

Lakeview

Kate

฿5,083

฿5,967 total

includes taxes & fees

3 Nov - 4 Nov

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

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

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

A modern interior with wooden flooring, black furniture, and large windows offering city views.

17. Hotel 505 River North

Downtown Chicago

Giana

฿7,698

฿10,229 total

includes taxes & fees

2 Nov - 3 Nov

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

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

18. Hyatt Place Chicago/River North

Downtown Chicago

Iminique

฿5,726

฿6,807 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

19. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

฿5,777

฿6,868 total

includes taxes & fees

3 Nov - 4 Nov

A dining table set for six with a cityscape view through large windows.

The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.

A modern hotel room with a large bed, a desk, a chair, and a view of the cityscape through large windows.

20. Swissotel - Chicago

Downtown Chicago

Hilary

฿6,429

฿8,828 total

includes taxes & fees

31 Oct - 1 Nov

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Stay near popular North Side attractions

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

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A sign for the Pritzker Family Children's Zoo surrounded by autumn foliage.

Lincoln Park Zoo

9.0/10 (1,096 reviews)

This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!

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A vintage car in a museum exhibit, a neon sign reading "GAS FOR LESS", and a historical mural on the wall.

Chicago History Museum

9.0/10 (37 reviews)

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

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A cityscape with a prominent clock tower, a mix of modern and historic buildings, and a dense skyline.

Park West

8.8/10 (12 reviews)

You can enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

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Vic Theatre

You can make plans for a show at Vic Theatre during your stay in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

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Theater Wit

You can get tickets for a performance at Theater Wit during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

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Second City

9.6/10 (15 reviews)

You can make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

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Lincoln Hall

You can get tickets for a performance at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

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Learn more about North Side

Venture to popular sights like Wrigley Field and Lake Michigan as you discover North Side.

See all hotels in North Side

A sign for Lincoln Park Conservatory in Chicago.

Top North Side Hotel Reviews

The Willows Hotel

8/10 Good

"Great charm in quaint surroundings. Very very clean!"

The Majestic Hotel

8/10 Good

"Nice historical building in quiet Lakeview. Chicago Cubs theme throughout. Solid place to stay. I didn't give it all 5's because this place is old and unless it is gut renovated, it won't have that clean, look and feel of a newer building. The staff were friendly. Our room was large with a separate bedroom and living space. The bed was comfortable, and the shower water pressure good and hot. I would recommend this hotel and will no doubt stay there again."

The Den Hotel

10/10 Excellent

"Was very clean !"

City Suites Hotel

10/10 Excellent

"Location was great, right next to train and bus station! Great room, loved the convenient mini bar. Nice friendly staff. Great stay!"

The Hotel at Midtown

10/10 Excellent

"Great stay, will stay there again"

Ray's Bucktown B&B

10/10 Excellent

"Thank you again for an amazing stay at Rays!"

The Villa Toscana

10/10 Excellent

"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."

The Neighborhood Hotel - Lincoln Park

10/10 Excellent

"It was a wonderful stay! Couldn't ask for a better experience."

Hotel Versey Chicago Lincoln Park

10/10 Excellent

"👍"

More cheap stays in North Side

Dorothy's

3445 N Halsted St Chicago IL

฿1,365

฿2,779 total

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (188 reviews)

The Villa Toscana

3447 N Halsted Chicago IL

฿1,913

฿3,591 total

2 Nov - 3 Nov

includes taxes & fees

The Den Hotel

3222 N Sheffield Ave Chicago IL

฿3,933

฿4,617 total

12 Oct - 13 Oct

includes taxes & fees

8.4/10 Very good! (117 reviews)

Wrigleyville Suites

3727 N Clifton Ave Chicago IL

฿5,083

฿5,967 total

3 Nov - 4 Nov

includes taxes & fees

Chicago Getaway Hostel

616 W Arlington Pl Chicago IL

Get rates

9/10 Wonderful! (1,000 reviews)

The Neighborhood Hotel - Lincoln Park

2616 North Clark Street Chicago IL

Get rates

9.2/10 Wonderful! (117 reviews)

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More ways to book

Book Hotels in North Side on Expedia.com

Find hotels in North Side, IL from ฿2,779

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in North Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for North Side hotels

1. Best Western Plus Hawthorne Terrace Hotel

2. Hotel Zachary Chicago, a Tribute Portfolio Hotel

3. The Hotel at Midtown

4. The Willows Hotel

5. The Majestic Hotel

6. Hotel Lincoln

7. City Suites Hotel

8. Hotel Versey Chicago Lincoln Park

9. Ray's Bucktown B&B

10. Dorothy's

11. Villa D' Citta

12. The Den Hotel

13. The Chicago Hotel Collection - Wrigleyville

14. The Villa Toscana

15. Wrigley Hostel

16. Wrigleyville Suites

17. Hotel 505 River North

18. Hyatt Place Chicago/River North

19. Hilton Vacation Club Hotel Blake Chicago

20. Swissotel - Chicago

Stay near popular North Side attractions

Wrigley Field

Lincoln Park Zoo

Chicago History Museum

Park West

Vic Theatre

Theater Wit

Second City

Lincoln Hall

Learn more about North Side

Top North Side Hotel Reviews

The Willows Hotel

The Majestic Hotel

The Den Hotel

City Suites Hotel

The Hotel at Midtown

Ray's Bucktown B&B

The Villa Toscana

The Neighborhood Hotel - Lincoln Park

Hotel Versey Chicago Lincoln Park

More cheap stays in North Side

Dorothy's

The Villa Toscana

The Den Hotel

Wrigleyville Suites

Chicago Getaway Hostel

The Neighborhood Hotel - Lincoln Park

Explore a world of travel with Expedia

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