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 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.

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

A spa area with a large indoor pool, exercise equipment, and potted plants.

1. Best Western Plus Hawthorne Terrace Hotel

Lakeview

Barbara

Rp4.815.907

Rp5.653.392 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

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

2. The Hotel at Midtown

Bucktown

Haili

Rp4.978.824

Rp6.790.636 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

A cozy interior with a wooden staircase, a seating area with chairs and a table, and shelves with various items.

3. Ray's Bucktown B&B

Bucktown

Susan

Rp3.306.147

Rp3.732.238 total

includes taxes & fees

29 Sept - 30 Sept

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

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.

A dining area with four tables and chairs, each with a small plant. There are two framed artworks on the walls.

4. The Willows Hotel

Lakeview

David

Rp3.462.297

Rp4.064.390 total

includes taxes & fees

28 Oct - 29 Oct

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

A cozy lounge area with green walls, wooden floors, and leather seating. There are tables and chairs arranged for dining and socializing.

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

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

5. The Majestic Hotel

Lakeview

Michael

Rp4.091.768

Rp4.803.613 total

includes taxes & fees

25 Oct - 26 Oct

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

A bedroom with a brick wall, a bed with white bedding, a nightstand with a lamp, and a framed sign that reads "NO LIGHTS! IN WRIGLEYVILLE".

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.

6. The Chicago Hotel Collection - Wrigleyville

Lakeview

Rob

Rp3.225.223

Rp3.786.090 total

includes taxes & fees

27 Oct - 28 Oct

A staircase with white railings and a chandelier.

A hotel entrance with a black awning, a gated entrance, and a number '3222' on the door.

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

7. The Den Hotel

Lakeview

Michael

Rp1.691.833

Rp1.986.044 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

A gym with treadmills and exercise equipment, wooden walls, and a large window.

8. Hotel Lincoln

Lincoln Park

Christopher

Rp3.473.182

Rp4.542.170 total

includes taxes & fees

29 Sept - 30 Sept

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

A modern hotel room with a large bed, a flat-screen TV, a sofa, and a city view.

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

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

9. Hotel Zachary Chicago, a Tribute Portfolio Hotel

Lakeview

Jeffrey

Rp6.167.046

Rp7.239.494 total

includes taxes & fees

4 Oct - 5 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 reception area with a counter, a floral wall mural, and a door in the background.

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

10. City Suites Hotel

Lakeview

Steven

Rp4.173.189

Rp4.898.906 total

includes taxes & fees

29 Sept - 30 Sept

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

A hotel named 'Versey' with outdoor planters and a clean sidewalk.

A modern living room with a sofa, a glass coffee table, and a decorative light fixture.

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

11. Hotel Versey Chicago Lincoln Park

Lakeview

Stephen

Rp2.829.032

Rp3.321.200 total

includes taxes & fees

26 Oct - 27 Oct

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

A kitchen with a dining table set for a meal, a dog sitting at the table, and various kitchen appliances and utensils.

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.

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

12. Dorothy's

Lakeview

Steven

Rp1.027.632

Rp1.832.943 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

A room with a wooden table, a coffee machine, a clock, and a framed sign on the wall.

13. Villa D' Citta

Lincoln Park

Jeffrey

Rp4.508.871

Rp5.293.022 total

includes taxes & fees

5 Oct - 6 Oct

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

A kitchen with a wooden table, four wooden chairs, a coffee maker, and various kitchen utensils.

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

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

14. The Villa Toscana

Lakeview

John

Rp1.358.838

Rp2.311.277 total

includes taxes & fees

26 Oct - 27 Oct

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 fireplace, a television mounted above it, and a large window with a view of trees.

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

15. Wrigleyville Suites

Lakeview

Kate

Rp2.658.595

Rp3.120.924 total

includes taxes & fees

29 Sept - 30 Sept

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

A wooden deck with a built-in seating area, a barbecue grill, and outdoor tables and chairs.

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

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

16. Wrigley Hostel

Lakeview

Shelly

Rp2.651.792

Rp3.112.974 total

includes taxes & fees

29 Oct - 30 Oct

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

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

17. L7 Chicago by LOTTE

Downtown Chicago

Emily

Rp5.188.289

Rp6.168.357 total

includes taxes & fees

1 Oct - 2 Oct

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

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

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.

18. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

Rp3.119.598

Rp3.708.889 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A spacious lobby with a marble floor, a reception desk, and a glass partition.

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

19. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

Rp4.231.617

Rp5.541.205 total

includes taxes & fees

25 Oct - 26 Oct

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

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

20. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

Rp5.654.484

Rp6.722.756 total

includes taxes & fees

14 Oct - 15 Oct

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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 large greenhouse with a green roof, surrounded by various trees and a metal sculpture.

Top North Side Hotel Reviews

The Chicago Hotel Collection - Wrigleyville

8/10 Good

"We stayed here on a Saturday night and there was very, very loud live music from the bars until after 1:30 am. I had to sleep with headphones on and rain sounds playing to drown the noise out. I didn't realize this hotel was on the main bar strip. Other than that, the hotel itself was nice."

Wrigley Hostel

10/10 Excellent

"Nice clean bathrooms clean bed and good free spaces to lounge Safe"

The Villa Toscana

10/10 Excellent

"Really nice little house on the main street of Boys Town, lovely front seating area."

The Den Hotel

10/10 Excellent

"This is a self service hotel. Very small and great for a quick trip. The hotel has been completely remodeled and beautiful. And tons of things to do around the hotel. Close to Wrigleyville and Boy's town."

The Hotel at Midtown

10/10 Excellent

"Fitness"

Hotel Zachary Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Great location for the cubs hame"

Villa D' Citta

10/10 Excellent

"This was the best lodging I've ever had in Chicago. Not sure I'd stay on Michigan Ave or in the Loop after this. A heartfelt thanks to the owners who trust the guests with such amenities."

The Neighborhood Hotel - Lincoln Park

8/10 Good

"Stellar location. The communication was a little lacking and slow to respond. Adorable and comfortable stay for a girls trip."

More cheap stays in North Side

Dorothy's

3445 N Halsted St Chicago IL

Rp1.027.632

Rp1.832.943 total

26 Oct - 27 Oct

includes taxes & fees

The Den Hotel

3222 N Sheffield Ave Chicago IL

Rp1.691.833

Rp1.986.044 total

30 Sept - 1 Oct

includes taxes & fees

8.4/10 Very good! (110 reviews)

The Villa Toscana

3447 N Halsted Chicago IL

Rp1.358.838

Rp2.311.277 total

26 Oct - 27 Oct

includes taxes & fees

8/10 Very good! (677 reviews)

Wrigleyville Suites

3727 N Clifton Ave Chicago IL

Rp2.658.595

Rp3.120.924 total

29 Sept - 30 Sept

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! (116 reviews)

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Book Hotels in North Side on Expedia.com

Find hotels in North Side, IL from Rp1.832.943

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. The Hotel at Midtown

3. Ray's Bucktown B&B

4. The Willows Hotel

5. The Majestic Hotel

6. The Chicago Hotel Collection - Wrigleyville

7. The Den Hotel

8. Hotel Lincoln

9. Hotel Zachary Chicago, a Tribute Portfolio Hotel

10. City Suites Hotel

11. Hotel Versey Chicago Lincoln Park

12. Dorothy's

13. Villa D' Citta

14. The Villa Toscana

15. Wrigleyville Suites

16. Wrigley Hostel

17. L7 Chicago by LOTTE

18. Hilton Chicago/Magnificent Mile Suites

19. Hotel Riu Plaza Chicago

20. Hilton Vacation Club Hotel Blake 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 Chicago Hotel Collection - Wrigleyville

Wrigley Hostel

The Villa Toscana

The Den Hotel

The Hotel at Midtown

Hotel Zachary Chicago, a Tribute Portfolio Hotel

Villa D' Citta

The Neighborhood Hotel - Lincoln Park

More cheap stays in North Side

Dorothy's

The Den Hotel

The Villa Toscana

Wrigleyville Suites

Chicago Getaway Hostel

The Neighborhood Hotel - Lincoln Park

Explore a world of travel with Expedia

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