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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for North Side vacation homes

A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

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

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is ￥21,981
￥109,524 total
includes taxes & fees
Sep 29 - Sep 30
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

2. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is ￥63,500
￥149,266 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

3. 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, (43 reviews)
"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...
United States
Andrea M.
The price is ￥59,690
￥116,168 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

4. 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 ￥100,786
￥329,991 total
includes taxes & fees
Sep 30 - Oct 1
Premier 9BR Art Deco manor with garage.

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is ￥13,883
￥89,582 total
includes taxes & fees
Sep 28 - Sep 29
Theater • Game Room • Gym • Firepit • 4BR Home

6. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is ￥17,145
￥52,500 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Studio Suite, Steps from River North & Shops
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

7. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
A quiet stay while you are away

8. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is ￥16,002
￥115,297 total
includes taxes & fees
Sep 30 - Oct 1
Arcade • Theater • Gym • Office • Sleeps 15
A modern living room with a sectional sofa, a coffee table, and a TV.

9. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is ￥28,575
￥36,894 total
includes taxes & fees
Sep 29 - Sep 30
Attractive Coach House Apartment for rent in Oak Park.
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (9 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 ￥41,561
￥171,207 total
includes taxes & fees
Oct 22 - Oct 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

11. 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, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is ￥23,574
￥47,637 total
includes taxes & fees
Sep 28 - Sep 29
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A single-story house with a covered porch, a front door, and a small garden area.

12. 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 ￥30,483
￥54,646 total
includes taxes & fees
Sep 29 - Sep 30
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A white two-story house with a porch, steps, and a small table with chairs.

13. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is ￥30,163
￥83,419 total
includes taxes & fees
Sep 29 - Sep 30
Oak Park Victorian by FLW Studio
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

14. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (44 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is ￥48,006
￥110,763 total
includes taxes & fees
Oct 8 - Oct 9
Chicago Riverhouse with private fenced in oasis
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

15. Spacious 4BR near Northwestern with King Beds + Crib

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, Exceptional, (5 reviews)
"Spacious home that accommodates all our guests. Very close to Northwestern University so travel was easy! Home was clean and well taken care of. Would definitely recommend to others and would stay agin when I’m in the area."
United States
Melissa C.
The price is ￥36,449
￥83,441 total
includes taxes & fees
Sep 30 - Oct 1
Spacious 4BR near Northwestern with King Beds + Crib
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

16. 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 ￥30,388
￥73,653 total
includes taxes & fees
Oct 19 - Oct 20
Classic Forest Park Foursquare < 1 Mi to Blue Line
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is ￥36,452
￥106,893 total
includes taxes & fees
Oct 1 - Oct 2
Game Room • Fire-pit • Playground • Gym • Billiard
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

18. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (23 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 ￥23,654
￥49,592 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Home by O'Hare + EV Plug
A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

19. Bronzeville Gem: Balcony, Gym & Rooftop Deck

Bronzeville Gem: Balcony, Gym & Rooftop Deck
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
The price is ￥51,564
￥111,286 total
includes taxes & fees
Sep 26 - Sep 27
Bronzeville Gem: Balcony, Gym & Rooftop Deck
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.
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Top North Side Hotel Reviews

The Majestic Hotel

The Majestic Hotel

10/10 Excellent
"Great place, close to the field"
Zane 1-night trip
Posted 12 hours ago
The Majestic Hotel

Find out more about North Side

North Side Vacation Homes information

Number of reviews
382
Accommodation
58 Vacation Homes
Lowest Price
￥36,894
Highest Price
￥329,991

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