A nighttime city skyline reflected in a calm body of water, with illuminated buildings and a bridge.

Search Vacation Homes in 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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for North Side vacation homes

A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

1. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

2. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Great location. Great place to stay. "
United States
Jill L.
The price is AED 1,050
AED 2,189 total
includes taxes & fees
15 Nov - 16 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern building with a large dome and circular design, surrounded by a landscaped area with trees and a water body.

3. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is AED 1,951
AED 6,577 total
includes taxes & fees
16 Nov - 17 Nov
Premier 9BR Art Deco manor with garage.
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveler
The price is AED 558
AED 3,164 total
includes taxes & fees
11 Nov - 12 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is AED 415
AED 1,758 total
includes taxes & fees
11 Nov - 12 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

6. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AED 412
AED 2,036 total
includes taxes & fees
11 Nov - 12 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

7. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
Chicago Riverhouse with private fenced in oasis
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

8. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (90 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is AED 393
AED 697 total
includes taxes & fees
16 Nov - 17 Nov
Master qtr close to nature & easy urban facilities
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

9. 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
7.8 out of 10, Good, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AED 545
AED 1,059 total
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A garage with a white door, brick pillars, and a car parked inside.

10. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is AED 624
AED 1,341 total
includes taxes & fees
12 Nov - 13 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A single-story house with a covered porch, a front door, and a small garden area.

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

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AED 760
AED 1,510 total
includes taxes & fees
11 Nov - 12 Nov
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is AED 468
AED 1,045 total
includes taxes & fees
1 Dec - 2 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

13. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is AED 597
AED 1,631 total
includes taxes & fees
15 Nov - 16 Nov
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

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

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 624
AED 946 total
includes taxes & fees
11 Nov - 12 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

15. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (65 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is AED 661
AED 1,293 total
includes taxes & fees
16 Nov - 17 Nov
LUXE 3 BR, 2 BA + Hot Tub
A modern kitchen with white cabinets, a black stove, and a microwave.

16. Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (83 reviews)
"It was a very clean place, comfortable furniture and beds e.c.t."
United States
Ronald H.
The price is AED 569
AED 1,081 total
includes taxes & fees
30 Nov - 1 Dec
Your Next Vacation Home
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

17. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (28 reviews)
"Host was very accommodating and everything about the stay was top notch. Loved the neighborhood as well. Next time we’re in Chicago area with a group of that size, this is the place I hope to stay!"
United States
Patrick R.
The price is AED 661
AED 1,281 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Home by O'Hare + EV Plug
A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

18. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
Firepit • Game Room • Theater • Gym • Sleeps 18
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

19. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is AED 705
AED 1,686 total
includes taxes & fees
11 Nov - 12 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A spacious living room with a blue sofa, a dining area with blue chairs, a kitchen with a white countertop, and a fireplace.

20. Spacious Des Plaines Home - Near Airport, Casino & Arena

Spacious Des Plaines Home - Near Airport, Casino & Arena
Des Plaines
8.0 out of 10, Very good, (2 reviews)
"It was a nice area."
United States
Sherice S.
Spacious Des Plaines Home - Near Airport, Casino & Arena
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 North Side Hotel Reviews

The Willows Hotel

The Willows Hotel

10/10 Excellent
"Not really many amenities to speak of. Very convenient location for me. Easy to get to, with bus and train nearby. Plenty of shops in all directions. Close to the lake. It’s very convenient to our daughter. We plan on making this our hotel for when we visit. Historic charm which I love!! Room was large, (which is rare for Chicago), extremely quiet, and had a comfortable bed. We’ve been hunting for a place to return to and I think that we found it. Coffee could be better and maybe something for a quick bite! But plenty of places nearby also."
Tari 4-night trip
Posted 6 hours ago
The Willows Hotel

Explore a world of travel with Expedia