Vacation rentals in Wrigleyville, Chicago

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Top-rated vacation rentals in Wrigleyville, Chicago

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Top guest favorite

A large dining table made of wood is surrounded by minimalist lighting fixtures. Natural light enters through multiple windows, highlighting the room's mix of exposed brick and modern furnishings. A cozy seating area is visible, featuring a sectional sofa and a television mounted on the wall.

Apartment in Lincoln Park

5 out of 5 average rating, 254 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest favorite

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in Avondale

4.95 out of 5 average rating, 103 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

Guest favorite

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in West Town

4.96 out of 5 average rating, 338 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

The exterior of a historic brownstone building is showcased, featuring a beautifully detailed entrance surrounded by brick and stone. A set of steps leads up to the front door, flanked by decorative wrought iron railings and lush greenery, creating a welcoming atmosphere.

Home in Lincoln Park

5 out of 5 average rating, 11 reviews

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

Superhost

A bright and open dining area features a wooden table surrounded by multiple white chairs. Large windows allow natural light to fill the space, highlighting a modern living room setup with a green sofa and a decorative plant.

Condo in Lincoln Park

4.8 out of 5 average rating, 160 reviews

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Guest favorite

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

Apartment in West Lake View

4.94 out of 5 average rating, 175 reviews

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!

Guest favorite

A modern bathroom is highlighted by a spacious walk-in shower featuring vibrant blue tiles and gold fixtures. A stylish, illuminated mirror above a contemporary vanity with blue cabinetry is visible, complemented by elegant marble flooring throughout the space.

Home in Lake View

4.88 out of 5 average rating, 169 reviews

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Top guest favorite

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Superhost

A bright living space features a sectional couch positioned around a glass coffee table. Large skylights and windows allow natural light to fill the room, which is accented by a decorative rug and a modern electric fireplace. A television hangs on one wall, displaying a scenic landscape.

Apartment in Logan Square

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Guest favorite

The entrance is characterized by elegant stone steps leading to two ornate wooden doors. Flanking the entry, flower boxes add a touch of color. The structure features large windows, allowing natural light to brighten the facade, and is complemented by a decorative wrought-iron fence.

Apartment in Lake View

4.94 out of 5 average rating, 115 reviews

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!

Guest favorite

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

4.95 out of 5 average rating, 104 reviews

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Top guest favorite

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Irving Park

4.96 out of 5 average rating, 280 reviews

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

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What guests are saying

Family-Friendly 2BD/2BA Prime Location (+parking)

4.91 out of 5 average rating, 94 reviews3 weeks ago

We really enjoyed this location, especially the ability to walk to so many restaurants nearby. Old Town is a neat little corridor with many shops and places to eat, and felt very safe to walk to. Speaking of safety, being that we were staying in the city, I had no idea what to expect, but this place felt very safe, there is a locked gate to get on the property, then through another locked door before getting to the front door. Needless to say we felt very secure. Everything was very clean and tidy, and we had everything we needed for the few days we were there. Communication was also excellent and really prompt, while also being personable and down to earth! Although parking passes were provided, be aware that parking will likely be a challenge. We were only able to park using the zone pass once, and every other time we had to drive around for a while to find a spot, so be prepared to drop things off, park, and walk! Overall, great spot, great hosts! Definitely recommend.

Apartment in Old Town

What guests are saying

The Hidden Beach House

4.75 out of 5 average rating, 8 reviews1 month ago

I enjoyed my stay here. The accommodations were basic, but the place was very clean and quiet, I found the bed very comfortable, and the location was ideal for 1 to 2 people to base out of while enjoying Old Town. The Brown Line train is just a couple of blocks from the house, which made getting to the Loop very convenient. Caid was very easy to reach with any questions. I would stay here again. One recommendation: if you drive here and need a parking pass, make those arrangements well in advance of your arrival, because they can’t be provided at a moment’s notice. I waited until the day before to ask for one and could not get it, so I had to pay $90 to park in a garage.

Guest suite in Lincoln Park

What guests are saying

A Comfortable Stay While You are Away in Oak Park

4.85 out of 5 average rating, 68 reviews2 weeks ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

Home in Austin

What guests are saying

Private Downtown Retreat with Rooftop Oasis

4.98 out of 5 average rating, 43 reviewstoday

Florin was an amazing host! Seemless check in and wonderful location. I still can't believe how clean this place was. I'm very picky about cleanliness and I felt so comfortable no matter what room I was in. This was our first trip to Chicago and everything we needed was in walkable distance. The location was spot on and it was a very beautiful part of the city. This will definitely be our go to place to stay next time we are in the area.

Home in Near North Side

What guests are saying

Spacious 2 Bed Apartment, Perfect Location

4.89 out of 5 average rating, 73 reviews3 weeks ago

This is a quirky, comfortable place. It’s full of great books, interesting decor and Chicago charm. The apartment is quite large, it’s on the ground floor and there is back door access to the alley from the kitchen. The kitchen was full of cookware and there was a gas stove. I appreciated the coffee pot and large tin of Costco coffee. There was also a great selection of teas as well as many interesting mugs to choose from.

Apartment in Lake View

What guests are saying

Loyola & Lake -3br/2bth close to the Lake & Loyola

4.95 out of 5 average rating, 80 reviews3 months ago

My friends and I stayed for my birthday weekend and were super happy with everything, the fireplace is especially nice for cold chicago winters! We only had trouble finding street parking Saturday night when we got back from our concert at 3am but that was expected. This will be my go-to place for groups from now on!

Apartment in East Rogers Park