Holiday rentals in Lake View, Chicago

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Top-rated holiday rentals in Lake View, Chicago

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Superhost

Flat in Lake View

4.85 out of 5 average rating, 91 reviews

Pristine Lakeview| Boystown |Wrigley Haven |Beach

In the heart of historic trendy Boystown and Wrigleyville, this fully furnished quiet 1 BR/1 BA apartment with an equipped kitchen is in a vibrant culturally diverse neighborhood. 5 Minutes' drive to Downtown. It is steps from the beach, lakefront parks, and Belmont Harbor, and is within walking distance to many restaurants, boutique shops, amazing nightlife, many local theaters, and home of the World Series Champs, the CUBS. Enjoy 65inches Samsung QLED Tv Netflix, Hulu, Apple Music Fast Wi-Fi

Guest favourite

Apartment in Lake View

4.91 out of 5 average rating, 96 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Top guest favourite

Home in Lake View

4.98 out of 5 average rating, 257 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!

Guest favourite

Loft in Lake View

4.96 out of 5 average rating, 510 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.

Guest favourite

Flat in Wrigleyville

4.92 out of 5 average rating, 232 reviews

Taj Ma-small at Wrigley

I think you are just going to love my apartment. The space features wonderful large windows in both rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a four-minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's also a walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

Top guest favourite

Flat in Lake View

4.99 out of 5 average rating, 285 reviews

A Whimsical Fairy-tale Loft in Ravenswood Chicago

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. 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.

Top guest favourite

Guest suite in North Center

4.97 out of 5 average rating, 120 reviews

Modern Garden Apartment in Lincoln Square

Welcome to our stylish and updated one-bedroom apartment located in a classic brick building in Lincoln Square. Perfect for solo travelers or couples, the space features a comfortable queen bed and a bright, modern interior. Just a short walk to the Brown Line and steps from Lincoln Square’s cozy shops, top-rated restaurants, and vibrant local culture. Wrigley Field, downtown attractions, and Lske Michigan are easily accessible by bike or train.

Guest favourite

Flat in Wrigleyville

4.97 out of 5 average rating, 89 reviews

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.

Superhost

Flat in Wrigleyville

4.8 out of 5 average rating, 435 reviews

'Secret Garden' Apartment in Wrigleyville

Small garden unit in the heart of Wrigleyville. Steps from both Wrigley and Boystown. The apartment has a queen bed in the bedroom and a sitting area with a TV and mini-dining area. In addition, the apartment has mini fridge, microwave, coffee machine w/ pods, and small dining table. There is no kitchen; fortunately Chicago has a multitude of amazing restaurants to choose from! Includes full bathroom with shower and linens.

Guest favourite

Flat in West Lake View

4.95 out of 5 average rating, 120 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Guest favourite

Flat in West Lake View

4.96 out of 5 average rating, 28 reviews

NEW Wrigley Designer Flat on Southport Corridor

We invite you to spend your next trip in this beautifully remodeled studio flat in Chicago's iconic Lakeview neighborhood. Situated at the intersection of Southport and Addison, the location couldn't possibly be better. Countless trendy dining options, bars, shops, and more are just steps away, as well as the Southport Brown Line 'L' station, which links you directly to O'Hare.

Guest favourite

Flat in Lake View

4.94 out of 5 average rating, 239 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).