A busy indoor space with a high, curved ceiling and a large circular light fixture.

Holiday Homes in Far North Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Far North Side holiday homes

Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
The price is NZ$1,314
includes taxes & fees
16 July - 17 July
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
TV

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Great host any concerns that I had were addressed and handled!"
United States
Keana
The price is NZ$998
includes taxes & fees
15 July - 16 July
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (85 reviews)
"It was great! Very quiet and clean."
United States
Tony G.
The price is NZ$378
includes taxes & fees
4 Aug - 5 Aug
Master qtr close to nature & easy urban facilities
Smart TV

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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (29 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is NZ$519
includes taxes & fees
21 July - 22 July
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"2nd stay. Will stay again"
United States
Rusty D.
The price is NZ$552
includes taxes & fees
29 July - 30 July
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
The price is NZ$462
includes taxes & fees
21 July - 22 July
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Interior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
The price is NZ$924
includes taxes & fees
15 July - 16 July
Modern 3BR Apartment Near North Ave Shops
Fridge, microwave, oven, stovetop

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Property was the perfect size for our group. Neighborhood was quiet. Street parking was available directly in front of the house. Great experience!!!!"
United States
Justin C.
The price is NZ$917
includes taxes & fees
11 Aug - 12 Aug
Game Room • Fire-pit • Playground • Gym • Billiard
Interior

Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (44 reviews)
"Cozy home, perfect for a relaxting time away "
United States
Phoenicia
The price is NZ$535
includes taxes & fees
11 Aug - 12 Aug
Riverfront rental
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (30 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is NZ$686
includes taxes & fees
16 July - 17 July
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is NZ$718
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is NZ$622
includes taxes & fees
13 Aug - 14 Aug
Cozy Home by O'Hare + EV Plug
7 bedrooms, desk, iron/ironing board, travel cot

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (2 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is NZ$1,254
includes taxes & fees
15 July - 16 July
Arcade • Theater • Gym • Office • Sleeps 15
Dining

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (2 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is NZ$1,490
includes taxes & fees
15 July - 16 July
Sleeps 18 • 8BR • Game Room • Gym • Theater
Paper towels, dining tables

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
wheaton
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
The price is NZ$992
includes taxes & fees
15 July - 16 July
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Great stay"
United States
Steve T.
The price is NZ$647
includes taxes & fees
27 July - 28 July
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (76 reviews)
"This place was just what we needed. Super close to Allstate Arena, lots of food options nearby. Neighborhood was quiet and seemed very safe. Beds were comfortable, kitchen was fully stocked, had everything we needed for our 1 night stay!"
United States
Nikki B.
The price is NZ$647
includes taxes & fees
22 July - 23 July
Your Next Vacation Home
Exterior

New Bath! Near Chicago and O’Hare +Fenced yard + Game room!

New Bath! Near Chicago and O’Hare +Fenced yard + Game room!
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
The price is NZ$842
includes taxes & fees
15 July - 16 July
New Bath! Near Chicago and O’Hare +Fenced yard + Game room!
Smart TV, books

Oak Park, IL, entire house, short walk to train.

Oak Park, IL, entire house, short walk to train.
Oak Park
9.4 out of 10, Exceptional, (22 reviews)
"My kids were visiting from out of town to celebrate my husband's birthday. They enjoyed their stay. The location was great for all they wanted to do."
United States
Lori P.
Oak Park, IL, entire house, short walk to train.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Far North Side Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"One of the best hotels I’ve ever stayed in. All staff from reception, cleaners, breakfast attendants and security work so well together. They are friendly, go beyond, hard working and kind. The breakfast time was beyond amazing. Everything is always fully stocked, until last hour. Wide variety of items, clean and smoothly operated by a meticulous breakfast team. I spent my birthday here and they made it special with small details such as wishing me during breakfast with a cake. We were delayed by a day and they sorted it for me without a problem- thank you Anderson and Jessica. The location is perfect, round the corner from magnificent mile, a walk to oak beach and much more. I can’t wait to return!"
Sanaa 6-night trip
Posted 3 hours ago
Hotel Riu Plaza Chicago

Find out more about Far North Side

Far North Side Holiday Homes information

Number of reviews
540
Accommodation
361 Holiday Homes
Lowest Price
NZ$378
Highest Price
NZ$1,490

Explore a world of travel with Expedia