
Apartment holiday rentals in Wrigleyville
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Top-rated apartment rentals in Wrigleyville
Guests agree: these apartments are highly rated for location, cleanliness and more.

3br W/ Elevator, Patio & Laundry Near the Red Line
My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago! You'll love the neighborhood; its vibrant food and art scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city. If work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable. (Balcony maintained for Summer Season, Memorial Day-Labor Day)

Newly Renovated, Spacious 2BR in Andersonville
Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Stunning 5 Bedroom Gem Steps from Wrigley Field!
One of a kind, beautiful 5 bed, 2 full bath two-level condo inside of an amazingly well-appointed all brick building, just steps from Wrigley Field. Exposed brick in the living area, incredible kitchen with all new appliances, island, and top of the line cabinets & countertops. A large group can comfortably enjoy the their time together spreading out in the two living spaces with large smart TV's, five bedrooms, two full baths, a back deck, and secure, private garage parking for two vehicles!

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

3BR Heart of Wrigley, 5min Walk to train & Wrigley
• Superhosts! • 98/100 Walking Score • 3 min walk to Wrigley Field • 3 bedrooms, each with its own bed (3 queens) and 1 futon , comfortably sleeps, at least, 7 people • Close to public transportation - 4 min walk to Red Line train • 10 min walk to Boystown/Metro concert hall • Near restaurants and bars = walker's paradise • 3rd floor walk-up • Free street parking passes for up to two cars can be provided upon advanced request. Steet parking is based on first come, first serve basis.

Steps away from Wrigley Field!!
The Wrigley Home is a newly renovated 2-bedroom with spacious living room & dining room. Ideal location for groups & families as this family-friendly neighborhood is walking distance to train stops (Addison- Red Line & Southport- Brown Line), retail shops, bars, restaurants, parks, and more! You will feel like home with a large sofa, fireplace, dining room table, brand new kitchen appliances, the amenities of home, pack and play, high chair, stroller, toys, backyard for grilling, etc.

Roscoe Village One Bed Lux Apartment Near Wrigley
5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Modern vintage chic steps from Wrigley: park free
Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. Charming vintage DNA meets modern amenities. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom. Chicago Shared Housing Registration: R22000093584

Spacious 2 Bedroom in the heart of Lakeview!
Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

The Wrigley Flats | Chicago Vacation Rental
The Wrigley Flats is a unique Chicago vacation rental located 4 blocks south of Wrigley Field in city’s most sought after north side neighborhood---Wrigleyville! Our 3 bedroom | 1 bathroom flat can be rented for a weekend getaway, a week long vacation or an extended stay. Close proximity to Chicago’s lakefront, vibrant nightlife, the eclectic dining scene & of course Wrigley Field; it’s no wonder visitors flock here to get a taste of something amazing!

Beautiful Remodel in Sought After Wrigleyville
Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Quirky Quarters at Wrigley
I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.
Popular amenities for Wrigleyville apartment rentals
Weekly apartment rentals

The Winslow - Chic Studio by Wrigley Field

Deco Luxe Retreat 3BR • Steps to Wrigley + Garage

Shorter Walk To Wrigley Than A Home Run

2BR Apartment Beautifully Furnished

Lakeview Charmer -with parking!

Beautiful, sunny 2nd floor 3BR/1BA w free parking

Prime Location! 2BR Near Wrigley

Vibrant & Chic Apt On Quiet St in Andersonville
Private apartment rentals

Updated home with vintage charm

3 Bedroom Across from Wrigley Field AllStar Suite

The Cubs Dugout | 2 Level Retreat

Entire studio near Wrigley field

Private 2BR/2BA heart of Boystown walk to Wrigley

Charming Lakeview Oasis (parking included)

Fuzzy Master Bedroom (Entire Apt)

Charming 6BD Retreat - Steps Away from Wrigley
Apartment rentals with a hot tub

Spacious and Ideally located in the Lakeview area

Two bedrooms 2 bath by the Lake

Super Paradise+65 Amenities*Downtown 15 Min

Spacious Beautiful Condo

Spacious 2bdm unit 15min to Dwtn

Luxury 3BD Penthouse – Private Patio+Skyline Views

Belmont Pleasures - hot tub / arcade gaming room

The Downtown Oasis (Indoor Pool • Fitness Center)
Quick stats about flat rentals in Wrigleyville

Total holiday rentals
Explore 80 holiday rentals in Wrigleyville

Nightly prices starting at
Wrigleyville holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 7,600 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
80 of Wrigleyville holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wrigleyville rentals

4.9 Average rating
Wrigleyville stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Rentals with a patio Wrigleyville
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