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

Far North Side Vacation Rentals

  • 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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Far North Side vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,222 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is NT$5,480
NT$7,383 total
includes taxes & fees
Aug 19 - Aug 20
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (506 reviews)
"Perfect location"
United States
Diana
The price is NT$9,207
NT$11,605 total
includes taxes & fees
Aug 17 - Aug 18
Level Chicago – Old Town
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.6 out of 10, Exceptional, (167 reviews)
"Beautiful hotel, gardened a plus! Located in very nice neighborhood, near the train, breakfast was vey good well. Would stay there again"
United States
Jacob
The price is NT$4,782
NT$5,474 total
includes taxes & fees
Aug 20 - Aug 21
The Gem Museum Suites
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.8 out of 10, Excellent, (44 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is NT$8,222
NT$9,652 total
includes taxes & fees
Jul 26 - Jul 27
Wrigleyville Suites
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
Historic Oak Park Residence
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NT$6,951
NT$11,555 total
includes taxes & fees
Aug 17 - Aug 18
Historic Oak Park Home
Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NT$7,803
NT$12,530 total
includes taxes & fees
Jul 26 - Jul 27
At Home in Oak Park
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$5,886
NT$10,336 total
includes taxes & fees
Aug 3 - Aug 4
The Oak Park Loft
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"My Fourth of July weekend stay was nothing short of extraordinary. From the moment I arrived, I was welcomed with an incredible level of hospitality, professionalism, and attention to detail that immediately set the tone for an unforgettable experience. Every aspect of my stay exceeded my expectations, and I can confidently say this property understands what exceptional hospitality and outstanding guest service should look like. My Fourth of July weekend stay was nothing short of extraordinary. From the moment I arrived, I was welcomed with an incredible level of hospitality, professionalism, and attention to detail that immediately set the tone for an unforgettable experience. Every aspect of my stay exceeded my expectations, and I can confidently say this property understands what exceptional hospitality and outstanding guest service should look like. The accommodations were absolutely stunning. My room was beautifully presented, exceptionally clean, spacious, comfortable, and thoughtfully maintained. Everything felt polished and inviting, creating the perfect environment to relax and unwind throughout the holiday weekend. You can truly tell that attention is given to the smallest details, and those details made a tremendous difference in the overall experience. However, what elevated this stay from wonderful to truly exceptional was the staff. The level of service I received was remarkable. Every staff member I encountered was warm, courteous, attentive, and professional."
Cardez 2-night trip
Posted less than an hour ago
Hyatt Regency O'Hare Chicago

Find out more about Far North Side

Search for holiday rentals in Far North Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Far North Side using one of the methods below:

  • View our selection of featured holiday rentals in Far North Side
  • Use the map to find apartments and other holiday homes in the Far North Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Far North Side while they last

Look no further and take a look at our great range of rental properties in Far North Side!

Explore a world of travel with Expedia