North Side Holiday Rentals, Chicago: Private House Rentals

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Our top choices for North Side hotels

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

An outdoor seating area with tables and chairs, string lights, and umbrellas.

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

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

1. The Hotel at Midtown

Bucktown

Haili

Rp4.999.682

Rp6.819.084 total

includes taxes & fees

4 Oct - 5 Oct

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

Rp5.897.863

Rp6.923.502 total

includes taxes & fees

4 Oct - 5 Oct

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.

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

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

3. The Willows Hotel

Lakeview

John S

Rp3.476.802

Rp4.081.419 total

includes taxes & fees

28 Oct - 29 Oct

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

4. Best Western Plus Hawthorne Terrace Hotel

Lakeview

Barbara

Rp3.757.402

Rp4.410.814 total

includes taxes & fees

30 Sept - 1 Oct

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 green walls, wooden floors, and leather seating. There are tables and chairs arranged for dining and socializing.

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

5. The Majestic Hotel

Lakeview

Michael

Rp3.219.860

Rp3.780.054 total

includes taxes & fees

30 Sept - 1 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 room with a large bed, a chair, a nightstand, and a wall with a Chicago Cubs mural.

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".

6. Hotel Versey Chicago Lincoln Park

Lakeview

Stephen

Rp2.846.637

Rp3.341.866 total

includes taxes & fees

26 Oct - 27 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 hotel lobby with a reception desk, leather seating, a patterned rug, and a wall with various artworks.

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

7. Hotel Lincoln

Lincoln Park

Christopher

Rp3.254.018

Rp4.286.854 total

includes taxes & fees

1 Oct - 2 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 dining area with a fireplace, a wooden table, and chairs. There is a kitchen area with cabinets and appliances.

8. City Suites Hotel

Lakeview

Steven

Rp2.896.256

Rp3.399.999 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

9. Ray's Bucktown B&B

Bucktown

Susan

Rp3.417.078

Rp3.857.539 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

10. Dorothy's

Lakeview

Steven

Rp903.394

Rp1.689.724 total

includes taxes & fees

30 Sept - 1 Oct

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

The Chicago Hotel Collection entrance with a marquee sign and two red buttons on the wall.

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

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".

11. The Chicago Hotel Collection - Wrigleyville

Lakeview

Rob

Rp3.238.734

Rp3.801.948 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 living room with a fireplace, a sofa, a staircase, and a door.

12. The Den Hotel

Lakeview

Michael

Rp1.698.921

Rp1.994.363 total

includes taxes & fees

4 Oct - 5 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 stone entrance with a black metal gate, a black mat, and two lion statues.

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

Rp4.527.759

Rp5.315.196 total

includes taxes & fees

7 Oct - 8 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 kitchen with a wooden table, four wooden chairs, a coffee maker, and various kitchen utensils.

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

14. The Villa Toscana

Lakeview

John

Rp1.216.212

Rp2.146.753 total

includes taxes & fees

5 Oct - 6 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 living room with a fireplace, a television mounted above it, and a large window with a view of trees.

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

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

15. Wrigleyville Suites

Lakeview

Kate

Rp2.669.733

Rp3.134.000 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

16. Wrigley Hostel

Lakeview

Shelly

Rp2.894.458

Rp3.398.022 total

includes taxes & fees

19 Oct - 20 Oct

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

A modern room with a view of a river and high-rise buildings.

17. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Sharee

Rp4.553.827

Rp5.948.711 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.

18. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

Rp4.249.344

Rp5.564.419 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

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

Rp4.470.050

Rp5.314.656 total

includes taxes & fees

14 Oct - 15 Oct

The Intercontinental hotel facade with a large American flag and a floral display.

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

A person sitting by a window with a cityscape view.

A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

20. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Kenan

Rp4.728.214

Rp6.250.605 total

includes taxes & fees

25 Oct - 26 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 Den Hotel

10/10 Excellent

"The hotel is very well located for train and bus service and room was quiet for sleeping"

The Chicago Hotel Collection - Wrigleyville

10/10 Excellent

"Great location, walkable to many cute neighborhoods, restaurants and bars. Great room and beautiful rooftop deck"

The Majestic Hotel

10/10 Excellent

"Friendly and helpful staff with very good houses. Location fantastic - 5 minute walk from Lakefront and 10 minute walk from Wrigley Field."

The Willows Hotel

10/10 Excellent

"Great location! Walkable to so many neighborhoods & activities."

City Suites Hotel

10/10 Excellent

"If you want to be close to the action in the city, this is a wonderful place. Right next to the Belmont train station. Also, the rooms are spacious and lovely. Great stay."

Hotel Zachary Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Without question the best location when staying in Wrigleyville. The restaurant options at street level are a definite bonus. Will be staying there again."

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 Hotel at Midtown

10/10 Excellent

"Fitness"

More cheap stays in North Side

Dorothy's

3445 N Halsted St Chicago IL

Rp903.394

Rp1.689.724 total

30 Sept - 1 Oct

includes taxes & fees

The Den Hotel

3222 N Sheffield Ave Chicago IL

Rp1.698.921

Rp1.994.363 total

4 Oct - 5 Oct

includes taxes & fees

8.6/10 Excellent! (112 reviews)

The Villa Toscana

3447 N Halsted Chicago IL

Rp1.216.212

Rp2.146.753 total

5 Oct - 6 Oct

includes taxes & fees

8/10 Very good! (677 reviews)

Wrigleyville Suites

3727 N Clifton Ave Chicago IL

Rp2.669.733

Rp3.134.000 total

30 Sept - 1 Oct

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 Rp1.689.724

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. The Hotel at Midtown

2. Hotel Zachary Chicago, a Tribute Portfolio Hotel

3. The Willows Hotel

4. Best Western Plus Hawthorne Terrace Hotel

5. The Majestic Hotel

6. Hotel Versey Chicago Lincoln Park

7. Hotel Lincoln

8. City Suites Hotel

9. Ray's Bucktown B&B

10. Dorothy's

11. The Chicago Hotel Collection - Wrigleyville

12. The Den Hotel

13. Villa D' Citta

14. The Villa Toscana

15. Wrigleyville Suites

16. Wrigley Hostel

17. LondonHouse Chicago, Curio Collection by Hilton

18. Hotel Riu Plaza Chicago

19. Hilton Vacation Club Hotel Blake Chicago

20. InterContinental Chicago Magnificent Mile by IHG

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 Den Hotel

The Chicago Hotel Collection - Wrigleyville

The Majestic Hotel

The Willows Hotel

City Suites Hotel

Hotel Zachary Chicago, a Tribute Portfolio Hotel

Wrigley Hostel

The Villa Toscana

The Hotel at Midtown

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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