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.

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

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

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

1. The Hotel at Midtown

Bucktown

Robert

5.914.568 ₫

8.310.239 ₫ total

includes taxes & fees

1 Nov - 2 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.

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.

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

2. Hotel Zachary Chicago, a Tribute Portfolio Hotel

Lakeview

Madaline

6.576.917 ₫

7.720.644 ₫ 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 dining area with four tables and chairs, each with a small plant. There are two framed artworks on the walls.

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

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

3. The Willows Hotel

Lakeview

daniel

3.108.874 ₫

3.649.508 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

4. Best Western Plus Hawthorne Terrace Hotel

Lakeview

Barbara

4.889.997 ₫

5.740.368 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

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

5. Hotel Versey Chicago Lincoln Park

Lakeview

Stephen

2.858.967 ₫

3.356.340 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

6. The Majestic Hotel

Lakeview

Toby

3.209.028 ₫

3.767.302 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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.

A hotel entrance with a marquee sign reading 'HOTEL LINCOLN' and '1816 CLARK'.

7. Hotel Lincoln

Lincoln Park

Means

3.239.146 ₫

4.474.356 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

8. City Suites Hotel

Lakeview

Vincentius

3.001.268 ₫

3.523.126 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

9. Ray's Bucktown B&B

Bucktown

Lora

5.197.110 ₫

5.866.962 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A staircase with white railings and a chandelier.

A living room with a fireplace, a sofa, a staircase, and a 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 hotel entrance with a black awning, a gated entrance, and a number '3222' on the door.

10. The Den Hotel

Lakeview

David

3.213.427 ₫

3.772.240 ₫ total

includes taxes & fees

25 Oct - 26 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 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 kitchen with a dining table set for a meal, a dog sitting at the table, and various kitchen appliances and utensils.

11. Dorothy's

Lakeview

Mick

1.032.333 ₫

2.117.410 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

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

12. Villa D' Citta

Lincoln Park

Hernando

6.516.115 ₫

7.649.352 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

13. The Chicago Hotel Collection - Wrigleyville

Lakeview

Rob

3.205.132 ₫

3.762.505 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

1.741.770 ₫

3.079.583 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

15. Wrigley Hostel

Lakeview

Shelly

2.380.316 ₫

2.794.284 ₫ total

includes taxes & fees

11 Nov - 12 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 living room with a television, a sofa, a chair, and a coffee table. There are windows and a clock on the wall.

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.

16. Wrigleyville Suites

Lakeview

Jainul

4.144.855 ₫

4.865.647 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

17. Hotel 505 River North

Downtown Chicago

Giana

4.631.267 ₫

6.334.373 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A person sitting by a window with a cityscape view.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

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

18. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Reginald

5.485.076 ₫

7.426.762 ₫ total

includes taxes & fees

31 Oct - 1 Nov

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

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

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

A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

19. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

4.446.016 ₫

5.286.112 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

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.

20. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

4.400.997 ₫

5.232.345 ₫ total

includes taxes & fees

1 Nov - 2 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)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

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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)

Visit the animals who live at Lincoln Park Zoo during your trip to Chicago. Experience the fascinating museums and entertainment choices in this vibrant area.

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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)

You can spend an afternoon studying the exhibits at Chicago History Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

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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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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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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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Concord Music Hall

Concord Music Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

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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

City Suites Hotel

10/10 Excellent

"I love that hotel. No frills but perfect setup for a mixed business and fun trip. Walking distance to Wrigley, restaurants and entertainment and right by the red line station. Will stay there again."

The Chicago Hotel Collection - Wrigleyville

8/10 Good

"The room was great very clean unique fun. The location is also very good. Lots to do. Lots of restaurants nearby things to walk to close to Wrigley Field. The check process what’s difficult had to wait like 20 minutes via several phone calls to figure out how to get in . Had to call the number on the door several times before talking to someone that explained how to get our key. Looks like the lobby decor was supposed to be shabby chic, but it was just shabby talk to some other people checking in. They were somewhat disappointed at the look of the lobby all that being said, we would stay there again due to the nice rooms and great location"

Hotel Lincoln

10/10 Excellent

"Loved everything about the hotel with the exception of the coffee shop in the lobby. They never had anything. No decaf espresso beans, no pastries, limited sparkling drinks in cold case. On the second day, it was the same thing. The barista actually referred us to a coffee shop around the corner! If I was hotel Lincoln, I would be careful recommending the coffee shop if they’re going to be so ill prepared. The restaurant in the lobby is a different story! What a great place to eat. Service was great with helpful staff and great food. M6 son who lives nearby (reason for trip) didn’t 3pm know the restaurant was there, but he does now. Very pleased with the restaurant! Thanks again for a great weekend"

The Hotel at Midtown

10/10 Excellent

"When I'm in Chicago, this is the only hotel that I want to stay at going forward!!"

The Den Hotel

10/10 Excellent

"Great location for a night. This particular room had an external bathroom, but was private to us. We just had to walk through a hallway to get to it. We did not encounter any problems or other guests. We parked in The Vic public parking structure down a couple of blocks - it was $23 to park for the night: We would definitely stay here again."

Best Western Plus Hawthorne Terrace Hotel

10/10 Excellent

"Great location and wonderful room. The shower got hot fast, they supply plenty of towels and the beds are very comfortable. Parking is convenient and there are several restaurants right across the street and next door. Would definitely stay again!"

Hotel Versey Chicago Lincoln Park

10/10 Excellent

"We had a great stay overall! The staff was friendly, welcoming, and helpful, and the hotel and surrounding area were clean and felt safe. The only minor issues were with the room itself. It was quite hot, even with the window open, and the street noise was noticeable. However, we spent very little time in the room, so it wasn’t a major issue for us. One thing to note is that the parking information listed valet parking, but valet service was not available. Instead, there is a self-parking garage just a short walk from the hotel. Other than these small inconveniences, everything was great. The friendly staff, cleanliness, and safe location made for a very pleasant stay. With a cooler, quieter room and more accurate parking information, this would easily be a five-star experience. We would definitely consider staying here again! Oh and if stay go to the restaurant for a burger and tots you won't be disappointed"

Hotel Zachary Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Beautiful hotel, and perfect location."

Dorothy's

10/10 Excellent

"Fun unique apartment above a wonderful pizza place! Great location and the stay was just great!"

More cheap stays in North Side

Dorothy's

3445 N Halsted St Chicago IL

1.032.333 ₫

2.117.410 ₫ total

16 Nov - 17 Nov

includes taxes & fees

8.6/10 Excellent! (192 reviews)

The Villa Toscana

3447 N Halsted Chicago IL

1.741.770 ₫

3.079.583 ₫ total

16 Nov - 17 Nov

includes taxes & fees

8/10 Very good! (682 reviews)

The Den Hotel

3222 N Sheffield Ave Chicago IL

3.213.427 ₫

3.772.240 ₫ total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (126 reviews)

Wrigleyville Suites

3727 N Clifton Ave Chicago IL

4.144.855 ₫

4.865.647 ₫ total

3 Nov - 4 Nov

includes taxes & fees

7.6/10 Good! (64 reviews)

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

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Book Hotels in North Side on Expedia.com

Find hotels in North Side, IL from 2.117.410 ₫

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. Hotel Versey Chicago Lincoln Park

6. The Majestic Hotel

7. Hotel Lincoln

8. City Suites Hotel

9. Ray's Bucktown B&B

10. The Den Hotel

11. Dorothy's

12. Villa D' Citta

13. The Chicago Hotel Collection - Wrigleyville

14. The Villa Toscana

15. Wrigley Hostel

16. Wrigleyville Suites

17. Hotel 505 River North

18. InterContinental Chicago Magnificent Mile by IHG

19. Hilton Vacation Club Hotel Blake Chicago

20. L7 Chicago by LOTTE

Stay near popular North Side attractions

Wrigley Field

Lincoln Park Zoo

Chicago History Museum

Park West

Vic Theatre

Second City

Theater Wit

Concord Music Hall

Learn more about North Side

Top North Side Hotel Reviews

City Suites Hotel

The Chicago Hotel Collection - Wrigleyville

Hotel Lincoln

The Hotel at Midtown

The Den Hotel

Best Western Plus Hawthorne Terrace Hotel

Hotel Versey Chicago Lincoln Park

Hotel Zachary Chicago, a Tribute Portfolio Hotel

Dorothy's

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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