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Check prices for these dates

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

Our top choices for North Side vacation homes

Interior

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

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
4 BR • Theater Room • Gym • Walk to Lincoln Park!
Beach nearby

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 AED 1,469
AED 3,454 total
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Interior

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 AED 1,381
AED 2,688 total
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Coffee/tea maker, fridge, microwave, oven

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 AED 2,332
AED 7,635 total
includes taxes & fees
30 Sep - 1 Oct
Premier 9BR Art Deco manor with garage.
Game room

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 AED 322
AED 2,079 total
includes taxes & fees
28 Sep - 29 Sep
Theater • Game Room • Gym • Firepit • 4BR Home
Interior

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 AED 397
AED 1,215 total
includes taxes & fees
27 Sep - 28 Sep
Cozy Studio Suite, Steps from River North & Shops
Exterior

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
7 bedrooms, desk, iron/ironing board, travel crib

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 AED 370
AED 2,668 total
includes taxes & fees
30 Sep - 1 Oct
Arcade • Theater • Gym • Office • Sleeps 15
Living area

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 AED 661
AED 854 total
includes taxes & fees
29 Sep - 30 Sep
Attractive Coach House Apartment for rent in Oak Park.
Dining

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 AED 977
AED 3,980 total
includes taxes & fees
22 Oct - 23 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
Smart TV

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 AED 545
AED 1,102 total
includes taxes & fees
28 Sep - 29 Sep
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior

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 AED 694
AED 1,253 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Exterior detail

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 AED 698
AED 1,930 total
includes taxes & fees
29 Sep - 30 Sep
Oak Park Victorian by FLW Studio
Outdoor dining

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 AED 1,111
AED 2,563 total
includes taxes & fees
8 Oct - 9 Oct
Chicago Riverhouse with private fenced in oasis
Dining

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 AED 843
AED 1,931 total
includes taxes & fees
30 Sep - 1 Oct
Spacious 4BR near Northwestern with King Beds + Crib
Coffee/tea maker, fridge, microwave, stovetop

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 AED 705
AED 1,764 total
includes taxes & fees
27 Sep - 28 Sep
Classic Forest Park Foursquare < 1 Mi to Blue Line
Coffee/tea maker, fridge, microwave, oven

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 AED 843
AED 2,473 total
includes taxes & fees
1 Oct - 2 Oct
Game Room • Fire-pit • Playground • Gym • Billiard
Interior

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 AED 547
AED 1,171 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Home by O'Hare + EV Plug
3 bedrooms, iron/ironing board, travel crib, WiFi

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 AED 1,111
AED 2,463 total
includes taxes & fees
26 Sep - 27 Sep
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 14 hours ago
The Majestic Hotel

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