Holiday houses in Lake View, Chicago

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Top-rated holiday rentals in Lake View, Chicago

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Guest favourite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 293 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

17 – 24 Sept

$1,982 AUD total

Guest favourite

Home in Lake View

4.98 out of 5 average rating, 205 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!

2 – 9 Oct

$2,223 AUD total

Guest favourite

Apartment in Edgewater

4.99 out of 5 average rating, 103 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a bus stop right around the corner and less than 10 miles from the heart of the city, your urban adventure awaits!

22 – 29 Jan

$1,967 AUD total

Guest favourite

Condo in Uptown

4.92 out of 5 average rating, 110 reviews

Stunning, Spacious, & Sun-Soaked 1br Uptown Condo

Perfect for any type of traveler, my bright and inviting one bedroom condo in Uptown is a sanctuary stocked with every amenity you could need! There's an organized workspace area if you bring your work with you to Chicago, a gorgeous sunroom with a sofa bed, and a beautiful kitchen stocked with everything you could need to whip up a delicious meal. Steps to the lakefront and Montrose Beach and just a 6-minute walk to the Wilson Red Line, you can't beat this location. Book today! Welcome!

19 – 26 Jan

$1,960 AUD total

Guest favourite

Apartment in Roscoe Village

4.96 out of 5 average rating, 237 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".,

19 – 26 Dec

$1,514 AUD total

Guest favourite

Guest suite in Lake View

4.95 out of 5 average rating, 175 reviews

1 mile from Wrigley Field

Private entrance In-law suite with full bathroom, kitchenette, bedroom with queen bed, living room with sleeper sofa, bathroom with tub/shower. Access to washer/dryer and back yard. 1 mile from Wrigley Field (20 min walk), steps from Southport Corridor with restaurants, bars, and shopping. 2 - 4 blocks to trains which will take you downtown. 1/2 block from Belmont bus which will take you to the lake (10 min ride). We live onsite so we are available for questions, directions, etc.

5 – 12 Sept

$2,105 AUD total

Guest favourite

Loft in Lake View

4.96 out of 5 average rating, 416 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.

21 – 28 Dec

$2,088 AUD total

Guest favourite

Apartment in Lake View

4.86 out of 5 average rating, 201 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.

2 – 9 July

$1,809 AUD total

Guest favourite

Apartment in Lake View

4.97 out of 5 average rating, 329 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.

29 Nov – 6 Dec

$1,901 AUD total

Guest favourite

Apartment in Lake View

4.99 out of 5 average rating, 228 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.

21 – 28 Jan

$1,963 AUD total

Guest favourite

Apartment in Uptown

4.96 out of 5 average rating, 265 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

14 – 21 Oct

$1,518 AUD total

Guest favourite

Apartment in Wrigleyville

4.8 out of 5 average rating, 384 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.

9 – 16 Sept

$1,901 AUD total