Apartment holiday rentals in Wrigleyville

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Top-rated apartment rentals in Wrigleyville

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A stylish living room features a mustard yellow couch and a round coffee table atop polished hardwood flooring. A large wall-mounted TV occupies one side, while a vibrant piece of abstract art is displayed. A dining area is visible in the background, adding to the home's open feel.
Apartment in Lincoln Park
4.88 out of 5 average rating, 224 reviews

Stunning 3 BR in prime Chicago location!

Enjoy the ultimate Chicago experience with a comfortable stay at this large, luxurious, sun-filled stylish 3BR condo. Unbeatable central location in an upscale Lincoln Park neighborhood puts all the very best of Chicago within easy reach. Surrounded by spectacular restaurants, bars, theaters and world-class architecture. 1200 acres of Lincoln Park, a world class Zoo, Wrigley Field, Navy Pier, Art Institute, River North and Downtown attractions are only a 5-10 minute ride or a quick train away.

Guest favourite
A bright, open living space showcases a cozy sectional sofa facing a large window surrounded by potted plants. A wooden dining table with white chairs is positioned in the foreground, complemented by a stylish area rug that defines the dining area.
Apartment in Logan Square
4.91 out of 5 average rating, 150 reviews

NEW Rehabbed Sunny top floor Logan Square

Beautiful, newly renovated three bedroom second (top) floor unit with one bathroom in the heart of Logan Square. Located on the Kimball bus line with free in-building laundry available and plenty of FREE street parking. There is a neighborhood mini mart one door down and a Divvy bike rental stand three blocks away. Come stay in Chicago's hottest neighborhood with some of the best dining and bars the city has to offer. *Fan of the hit TV series "The Bear"? Close to Giant, Pizza Lobo & Margies

Guest favourite
The living room features hardwood floors and exposed brick walls, creating a vibrant atmosphere. A comfortable sofa and two armchairs are arranged around a wooden coffee table. A fireplace is flanked by large windows dressed with soft drapes, while a mounted television adds modern convenience.
Apartment in Wrigleyville
4.92 out of 5 average rating, 103 reviews

WrigleyVilla - 1/2 Block From Wrigley Field!

Beautiful, private 3BR condo w/all the modern conveniences, just steps from Wrigley Field! Short walk to the El at Addison Red Line stop for easy access to everything Chicago! Discover dozens of shops, restaurants & taverns within walking distance on Clark, Halsted, Broadway, Southport & Irving Park Road, including grocery stores. Stay for a couple days, or a couple weeks - you'll have everything you need no matter what! If you don't find it, just ask - we're right downstairs and happy to help!

Guest favourite
Apartment in Uptown
4.9 out of 5 average rating, 199 reviews

Sunny Top-Floor Uptown Condo Near Lake & Red Line

Welcome to your home away from home in Uptown! My bright and inviting top-floor condo offers comfort and convenience, with a sunny living room for relaxing, a fully equipped kitchen and dining room, a spacious private bedroom, a serene sunroom with a full-size bed for extra guests, and a workspace for business travelers. Just a short walk from the lakefront and Montrose Beach, and only 6 minutes from the 24/7 Wilson Red Line, this location is ideal for exploring all that Chicago has to offer.

Top guest favourite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Apartment in Wicker Park
4.97 out of 5 average rating, 148 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Guest favourite
A modern living area features a blue sectional sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front of the sofa. A desk and chair are situated near a large window, allowing natural light to brighten the room.
Apartment in Irving Park
4.87 out of 5 average rating, 156 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Top guest favourite
An inviting outdoor area features a long wooden table surrounded by six woven chairs, set upon a patterned rug. Lush greenery envelops the space, with plants bordering the brick pathway, enhancing the natural ambiance. Soft lighting from overhead strands adds warmth to the setting.
Apartment in Lake View
4.99 out of 5 average rating, 201 reviews

Int. Designer’s Lakeview Duplex w/private backyard

A front door walkup duplex condo in the heart of Lakeview neighborhood. 2bed/2 bath with private office space. Surrounded by restaurants, bars and shops & just steps from the Wellington brown line train stop. Luxurious amenities such as designer toiletries, cooking oils/spices, cafe du monde coffee and various teas. Walk to nearby Wrigley, Lake, Lincoln Park Zoo or stay here and enjoy the private backyard garden with large lounge area, gas fireplace, grill, and 10 person dining table

Top guest favourite
The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.
Apartment in Lincoln Park
4.99 out of 5 average rating, 338 reviews

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

Guest favourite
A bedroom features a spacious bed with neatly stacked towels at its foot. A mural depicting a baseball player stands on one wall, complemented by a nearby mirror and door. The room is designed with light wood flooring and sports-themed decor.
Apartment in Wrigleyville
4.85 out of 5 average rating, 459 reviews

Authentic Condo steps from Wrigley Field!

There's no better place to stay if you are visiting Wrigley Field! You can't possibly get any closer to the action with the building being located at Waveland & Clark! Hear the crowd roar from inside the living room! - Recent major renovations! Brand new central heat and air system! Steps from public transportation, Clark Street night life & Wrigley Field. Large balcony in the back & an additional private balcony off the master bedroom den in the front of the building.

Guest favourite
A modern dining area features a wooden table surrounded by six chairs. Natural light enters through large windows, highlighting the grey walls and stylish cabinetry. A chandelier hangs above the table, while a wall-mounted art piece adds a decorative touch to the space.
Apartment in Wrigleyville
4.9 out of 5 average rating, 165 reviews

Foosball, Steps from Wrigley, Private Parking

Our apartment is ideally located near Wrigley Field and just steps from the Red Line, making it extremely convenient for exploring Chicago. Because of this prime location, occasional train and street noise can be heard. To help you sleep comfortably, we provide ear plugs. Many of our guests still enjoy the vibrant city atmosphere while finding the apartment cozy and restful. Perfect For: Guests who love being in the heart of Chicago and don’t mind a bit of city life sounds.

Top guest favourite
The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.
Apartment in Ukrainian Village
4.98 out of 5 average rating, 113 reviews

Ukrainian Village 3BR/3BA • Private Patio, Parking

Welcome to Ohio St — a beautifully designed 3-bedroom, 3-bathroom private home in the heart of Ukrainian Village. Featuring a jet tub in the master bath, front patio with hammock, back porch with gas grill, and rare gated private parking for 2 cars. Sleeps 7 comfortably. Steps from Wicker Park, Bucktown, West Town & Downtown Chicago. The entire home is yours — no shared spaces, no surprises. Perfect for families, groups, and extended stays.

Top guest favourite
The facade of a historic greystone building is showcased, featuring intricate stonework and large windows. A wrought-iron fence adorned with vibrant pink flowers is visible in the foreground, adding a touch of natural beauty to the entrance.
Apartment in Wrigleyville
4.99 out of 5 average rating, 113 reviews

Wrigleyville Inn. Historic Greystone, Free Parking

Have fun with the whole family at this stylish place. Completely rehabbed 3 bedroom 2 bathroom high end, 1st- floor condo in a historic greystone, 5-minutes walk to Wrigley Field. And only 2 minutes walk to Clark or Halsted Streets. New open back porch for your enjoyment. Parking included. Old Grey Lady being reborn. Total gut rehab of classic Chicago 3 flat located in Historic Newport Avenue District.

Popular amenities for Wrigleyville apartment rentals

Quick stats about apartment rentals in Wrigleyville

  • Total holiday rentals

    Explore 20 holiday rentals in Wrigleyville

  • Nightly prices starting at

    Wrigleyville holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 2,940 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Wrigleyville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wrigleyville rentals

  • 4.8 Average rating

    Wrigleyville stays are highly rated by guests – averaging 4.8 out of 5!

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