Vacation rentals with outdoor seating in Wrigleyville

4.9 out of 5 average rating, 536 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

An inviting living space features large windows allowing natural light, framed by exposed brick walls. A round dining table is surrounded by modern chairs, while a comfortable sectional sofa is positioned near a cozy fireplace, enhancing the warm ambience. Stylish decor elements add character to the room.

4.97 out of 5 average rating, 221 reviews

Modern vintage chic steps from Wrigley Field!

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. The vintage DNA is beautifully respected while updates provide the modern amenities you expect when traveling. 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.

4.91 out of 5 average rating, 185 reviews

The living area features high ceilings and large windows, allowing natural light to illuminate the space. A cozy sectional sofa is positioned around a coffee table, while a wall-mounted television hangs above a modern fireplace. Soft blue carpeting adds warmth to the decor.

Home in Wrigleyville

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, DRAMATIC SPACIOUS Loft condo w/ PRIVATE ROOFTOP overlooking skyline! Open 2-story layout w/7 individual bed options, 3 full bathrooms, fully-stocked kitchen + huge island. Enjoy luxury flooring, soaring high ceilings, keyless entry, 2 HD TVs, & grill. Perfect for special occasions! Next to Wrigley bars & restaurants. Train to Downtown only 12 mins. Private parking spaces for rent. Awarded "GUEST FAVORITE" badge! Host carries over 1275 5-star reviews across listings!

4.97 out of 5 average rating, 159 reviews

A comfortable living area showcases a modern design with a large flat-screen TV mounted on a stone feature wall. Soft lighting highlights a cozy seating arrangement, including a plush sofa and two armchairs. A decorative coffee table sits in the center, contributing to a welcoming atmosphere.

Apartment in Albany Park

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

Apartment in Roscoe Village

A bright living area features a comfortable gray sofa with decorative pillows, paired with two teal chairs. A mirrored wall accent adds depth, while a large flat-screen TV is mounted nearby. A coffee table with a zigzag area rug enhances the inviting space.

4.9 out of 5 average rating, 427 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.

4.98 out of 5 average rating, 267 reviews

A cozy living area features a light gray sofa with decorative pillows, alongside a wooden dining table and four stools at the breakfast bar. The kitchen is partially visible, showcasing stainless steel appliances and dark mahogany paneling.

Home in Lake View

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!

A vibrant garden is visible with two blue Adirondack chairs placed on lush green grass. Potted plants are scattered on a table in the foreground. In the background, a domestic cat can be seen among greenery and flowering plants, creating a serene outdoor setting.

4.97 out of 5 average rating, 312 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

A spacious living room is highlighted by a large sectional sofa adorned with colorful cushions. A flat-screen television sits opposite a cozy fireplace, framed by light-colored bricks. Two windows allow natural light to fill the room, enhancing the relaxed ambiance.

5 out of 5 average rating, 111 reviews

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.

A spacious seating area is defined by a dark upholstered sofa with yellow accent pillows. A modern gold-toned coffee table sits in front, resting on a textured woven rug. Art pieces adorn the walls, contributing to the room's thoughtful design.

5 out of 5 average rating, 315 reviews

An elegant Chicago Northside Getaway

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

A cozy living area displays a green sofa facing a TV cabinet with a flat-screen television. A round table is positioned in the center, surrounded by two ottomans. Light streams through the window, illuminating the patterned rug and creating an inviting space.

4.97 out of 5 average rating, 403 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.

4.84 out of 5 average rating, 437 reviews

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.

Condo in Wrigleyville

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.