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Wrigleyville, Chicago vacation rentals

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Top-rated vacation rentals in Wrigleyville, Chicago

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Rental unit in Lake View

4.84 out of 5 average rating, 279 reviews

Comfy/Elegant Home by Wrigley, Garage Spot & Yard

With two separate apartments, this chiq home near Wrigley Field is a hidden gem. It features comfortable beds, parking; and a fenced yard; with 3 bedrooms, 2 full baths, 2 spacious living & dining areas and fast gigabit internet. In an unbeatable location close to many popular attractions, this home is the perfect base for your Chicago adventures. 6 min drive to: -Andersonville & Boystown -Montrose Beach -Uptown, Green Mill, Riviera / Aragon Theaters 15 min drive: Cloudgate, Downtown, Loop!

Rental unit in North Center

4.9 out of 5 average rating, 188 reviews

Spacious Vintage 3 BR in Chicago's NorthCenter!

Location, location, location! Vintage 3BR second floor Apartment only 10 Blocks from Wrigley Field & 2 miles from Lake Michigan. Bus stop in front, CTA Brownline train to loop a 5 minute walk, bus/CTA from OHare airport 1 block away. Washing machine and dryer in apartment. Neighborhood setting. Walk to restaurants, local breweries, Old Town School of Folk Music & theaters, ballgames, concerts, Trader Joe's, banks, boutiques . Divy bikes, CVS & Starbucks across the street. Garage option.

Guest suite in Lake View

4.85 out of 5 average rating, 240 reviews

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

Rental unit in Roscoe Village

4.9 out of 5 average rating, 399 reviews

Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village

We converted our garden unit into a great space for travelers, we updated everything with you in mind, features high end appliances, full kitchen, 1 king and 1 queen pullout, heated floors, and free wifi. There are only 2 beds. We also have a landscaped backyard and grill access if requested If you need anything please let me know ahead of time Roscoe Village is often thought of as a small town inside the big city. It is one mile west of Wrigley Field and two miles west of the lakefront.

Home in Lake View

4.98 out of 5 average rating, 233 reviews

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

Rental unit in Lake View

4.93 out of 5 average rating, 197 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

Rental unit in Lake View

4.97 out of 5 average rating, 276 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

Rental unit in Roscoe Village

4.96 out of 5 average rating, 275 reviews

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".,

Loft in Lake View

4.95 out of 5 average rating, 462 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Rental unit in Lake View

4.85 out of 5 average rating, 228 reviews

Private Queen Bedroom and En Suite Bath

Visiting Chicago? Stay in true Windy City style by joining us in our historic 3-flat in the Lakeview neighborhood on Chicago's North Side within walking distance of Wrigley Field and the popular Southport Corridor of restaurants, bars and shops. We love hosting and can help you tailor an exploration of our city that is perfect for your interests or occasion. Walking access to the Red and Brown Elevated lines and buses at the end of the block can get you throughout Chicagoland.

Rental unit in Lake View

4.97 out of 5 average rating, 360 reviews

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Rental unit in Lake View

4.93 out of 5 average rating, 220 reviews

Quirky Designer Apartment - Steps from Wrigley!

Perfect for a weekend getaway in Chicago or to watch your team play a series at Wrigley Field. The perfect distance from the stadium: close enough for an easy walk to the stadium but far enough that you can get some sleep when you want to. Walking distance to restaurants, bars, shopping and public transportation. Street parking (pay by app).

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Popular amenities for Wrigleyville, Chicago vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Wrigleyville, Chicago's top sights

Wrigley Field1,004 locals recommend

Boystown92 locals recommend

Wrigley View Rooftop999 locals recommend

Whole Foods Market836 locals recommend

Jewel-Osco675 locals recommend

Target394 locals recommend

Other great vacation rentals in Wrigleyville, Chicago

Guest suite in West Lake View

4.94 out of 5 average rating, 84 reviews

The Bosworth Chicago Lakeview/Wrigley w/parking

Rental unit in Wrigleyville

5 out of 5 average rating, 19 reviews

Tickled Pink

Rental unit in Lake View

4.94 out of 5 average rating, 32 reviews

Chicago Bear Den

Rental unit in West Lake View

4.95 out of 5 average rating, 97 reviews

Chic retreat near the best of Lakeview & Wrigley

Rental unit in Lake View

4.87 out of 5 average rating, 277 reviews

WELCOME TO NANCY'S PAD!

Rental unit in North Center

4.98 out of 5 average rating, 64 reviews

Charming 1 Bedroom Apartment - NorthCenter/Roscoe

Rental unit in Lake View

4.81 out of 5 average rating, 59 reviews

Cozy apartment in Lake View

Guest suite in Lake View

4.95 out of 5 average rating, 200 reviews

1 mile from Wrigley Field

Quick stats about vacation rentals in Wrigleyville, Chicago

Total rentals
110 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
9.2K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore