Search Vacation Homes in Far North Side

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Vacation Homes in Far North Side

Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Vacation Home in Worth

9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
$299 nightly
The price is $319
Dec 9 - Dec 10
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Exterior detail
Master qtr close to nature & easy urban facilities

Vacation Home in Riverwoods

9.8 out of 10, Exceptional, (73)
"It was a great respite."
United States
VIncent L.
$174 nightly
The price is $185
Dec 15 - Dec 16
Total with taxes and fees
Master qtr close to nature & easy urban facilities
Smart TV
Getaway Near ORD With Great Local Amenities

Vacation Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
$263 nightly
The price is $278
Dec 9 - Dec 10
Total with taxes and fees
Getaway Near ORD With Great Local Amenities
Terrace/patio
Riverfront rental

Vacation Home in South Elgin

9.8 out of 10, Exceptional, (34)
"Luci was an excellent host and our stay was great!"
United States
Michelle C.
$195 nightly
The price is $207
Dec 9 - Dec 10
Total with taxes and fees
Riverfront rental
Fitness facility
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Belmont Cragin

2.0 star property
$434 nightly
The price is $528
Dec 10 - Dec 11
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
Exterior detail
Vintage Urban Retreat

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (13)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$446 nightly
The price is $511
Dec 11 - Dec 12
Total with taxes and fees
Vintage Urban Retreat
Exterior
Coziest estate home 20 minutes to downtown

Vacation Home in Willow Springs

8.8 out of 10, Excellent, (15)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
United States
Gabriela N.
$372 nightly
The price is $398
Dec 9 - Dec 10
Total with taxes and fees
Coziest estate home 20 minutes to downtown
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Vacation Home in La Grange Highlands

10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
$254 nightly
The price is $271
Dec 11 - Dec 12
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Private kitchen
Cozy Home in Suburbs near Chicago - pet friendly

Vacation Home in Bridgeview

2.0 star property
$301 nightly
The price is $322
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Home in Suburbs near Chicago - pet friendly
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

Vacation Home in Wheaton

10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
$291 nightly
The price is $308
Dec 10 - Dec 11
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Vacation Home in Lisle

9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
$236 nightly
The price is $250
Dec 9 - Dec 10
Total with taxes and fees
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

8.0 out of 10, Very Good, (19)
"Very nice place "
United States
Elliot H.
$227 nightly
The price is $242
Dec 9 - Dec 10
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

Vacation Home in Elmhurst

8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
$327 nightly
The price is $350
Dec 12 - Dec 13
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub
Smart TV
Enamored in Elmhurst

Vacation Home in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
$465 nightly
The price is $493
Dec 11 - Dec 12
Total with taxes and fees
Enamored in Elmhurst
Fridge, microwave, oven, stovetop
Cozy Home by O'Hare + EV Plug

Vacation Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
$318 nightly
The price is $340
Dec 10 - Dec 11
Total with taxes and fees
Cozy Home by O'Hare + EV Plug
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
$456 nightly
The price is $522
Dec 11 - Dec 12
Total with taxes and fees
Modern Victorian Vibes ❤️ | Character & Charm
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Vacation Home in Skokie

10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
$656 nightly
The price is $702
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Vacation Home in Wood Dale

10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
$371 nightly
The price is $393
Dec 9 - Dec 10
Total with taxes and fees
Wonderful in Wood Dale, right by O’Hare airport!
TV
Modern 4BR Retreat Near MDW | LCP Collection

Vacation Home in Burbank

9.4 out of 10, Exceptional, (6)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
$428 nightly
The price is $458
Jan 8 - Jan 9, 2026
Total with taxes and fees
Modern 4BR Retreat Near MDW | LCP Collection
Fridge, microwave, oven, stovetop
Two Kings Chicago A unique royal environment, kingly comfort!

Vacation Home in Villa Park

10.0 out of 10, Exceptional, (1)
"Art & Milda were fantastic hosts! Very responsive to all inquiries and requests. The home was beautiful. Very comfy beds and recliners! So many perks you never knew you wanted. Will definitely stay again. Thank you Art & Milda!"
United States
Lisa V.
$395 nightly
The price is $419
Dec 10 - Dec 11
Total with taxes and fees
Two Kings Chicago A unique royal environment, kingly comfort!
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Great stay"
Ericka 2-night trip
Posted 5 hours ago
citizenM Chicago Downtown

Find out more about Far North Side

Far North Side Vacation Homes information

Number of reviews
415
Accommodation
336 Vacation Homes
Lowest Price
$185
Highest Price
$702

Explore a world of travel with Expedia