North Side Holiday Homes from £108: Search Holiday Homes in North Side

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for North Side holiday homes

ENVITAE Hotel, 4BR Luxury Modern Apartments

Near North Side

includes taxes & fees

25 Jun - 26 Jun

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Robertsdale

Jusu K.

includes taxes & fees

9 Jun - 10 Jun

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

Eduardo

includes taxes & fees

8 Jun - 9 Jun

Master qtr close to nature & easy urban facilities

Riverwoods

Nayeli A.

includes taxes & fees

14 Jun - 15 Jun

Attractive Coach House Apartment for rent in Oak Park.

Oak Park

kerston b.

includes taxes & fees

7 Jun - 8 Jun

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

includes taxes & fees

4 Jun - 5 Jun

Near Lake and Museum • Modern • Game Area

South Shore

includes taxes & fees

7 Jun - 8 Jun

Game Room • Fire-pit • Playground • Gym • Billiard

Belmont Cragin

includes taxes & fees

4 Jun - 5 Jun

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

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

Top North Side Hotel Reviews

City Suites Hotel

10/10 Excellent

"I was really happy with my 6 night stay at City Suites in Chicago.The location, within walking steps of the Belmont " L:" stop is fantastic. I watched the trains come and go outside my window.But yet I was never bothered by noise coming from the trains when I was in my room.The hotel property, while it is older, has been beautifully maintained.The staff was professional.And I really appreciated the daily maid service.I forget how nice it is to have my bed made daily, fresh towels, and garbage removed without my having to request it.I felt pampered! There was a problem with low water pressure in the shower.But I dealt with that.I would definitely stay at City Suites again!"

Best Western Plus Hawthorne Terrace Hotel

10/10 Excellent

"Super cute hotel, great parking lot with EV charging stations. Front desk staff could have been more helpful. Two young women working when I checked in and then had a question about parking the next day made me feel like I was taking them away from something more important."

The Neighborhood Hotel - Lincoln Park

10/10 Excellent

"Great stay and exactly what we needed. Instructions were clear and everything we needed was marked. Beds were cozy and spacious. Only thing (not enough to lower my rating) is there was more pet fur from previous tenants on a lot of the furniture—especially the more velvet chairs—than we were expecting. The chairs could use a good washing/spot cleaning too. Also, the shower pressure in the primary bath was lower. However, we really enjoyed this stay and would come again!"

The Majestic Hotel

10/10 Excellent

"Everything was incredible! The Majestic is very close to Wrigley Field, so the baseball theme was everywhere - from the lobby to the hotel room (: the staff was incredibly friendly and were so nice. We arrived a lot later than we anticipated (think around midnight the next day) and the staff could see we were incredibly tired and were so friendly so late at night! (: the elevator up also had places to visit along with their distance from the hotel. We ended up going to Ann Sather on that recommendation and because it was a 10 min walk away. It’s also very close to the running trails along the water which my fiance loved! The area is super safe and I highly recommend staying there if you want access to good food, the lake, and want to tour Wrigley field. Additionally, we took the cta bus into the city and it didn’t take long at all (roughly 20 mins)!! It’s a great location - quiet, safe, walkable and overall just so welcoming (:"

Dorothy's

10/10 Excellent

"The location is perfect, ideal for party and celebration in bar and getting to know Boystown. The bathroom area and bed very clean and comfortable. *Uncover the closets in the room for convenience of storing suitcases and travel items. ——————————————————————— La ubicación es perfecta, ideal para pasar días de fiesta y de conocer boystown. El área de baños y cama muy limpias y cómodas. Cosas a mejorar: Desayuno (9am solo quedaba cereal para desayunar) Desocupar los closet de la habitación para comodidad de guardar maletas y artículos de viaje."

Hotel Zachary Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"The staff was incredible; friendly, accommodating, and helpful! The room was wonderful too, clean and so peaceful! The view of Wrigley Stadium is unmatched! The parking garage convenience made the stay even more comfortable with the ability to explore around the areas and still travel out to a same and secure parking and any time. Chicago as a whole was beautiful and next time I return I can’t think of staying anywhere else!"

Find out more about North Side

North Side Holiday Homes information

Number of reviews	26,631
Accommodation	65 Holiday Homes
Lowest Price	£108
Highest Price	£582

Explore a world of travel with Expedia

Flights to Chicago

Book Holiday Homes in North Side on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for North Side holiday homes

ENVITAE Hotel, 4BR Luxury Modern Apartments

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Master qtr close to nature & easy urban facilities

Attractive Coach House Apartment for rent in Oak Park.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Near Lake and Museum • Modern • Game Area

Game Room • Fire-pit • Playground • Gym • Billiard

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

Cozy Home by O'Hare + EV Plug

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Des Plaines / Chicago Midcentury 2-Bedroom Guesthouse

LUXE 3 BR, 2 BA + Hot Tub

Your Next Vacation Home

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Spacious Deck & Balcony, Game Area, Garage

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Modern 3BR Apartment Near North Ave Shops

Find holiday rentals that suit your style

Top North Side Hotel Reviews

City Suites Hotel

Best Western Plus Hawthorne Terrace Hotel

The Neighborhood Hotel - Lincoln Park

The Majestic Hotel

Dorothy's

Villa D' Citta

Hotel Lincoln

The Willows Hotel

Hotel Zachary Chicago, a Tribute Portfolio Hotel

Find out more about North Side

North Side Holiday Homes information

Explore a world of travel with Expedia