Vacation rentals in Lake View

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Top-rated vacation rentals in Lake View

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A spacious recreational area features a ping pong table, a large flat-screen TV, and comfortable leather seating. A coffee table sits in front of the couch adorned with a colorful quilt. Exercise weights are positioned on the floor, adding to the diverse amenities of the space.
Guest suite in Lake View
4.85 out of 5 average rating, 273 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.

Top guest favourite
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.
Apartment in Lake View
4.97 out of 5 average rating, 337 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

Guest favourite
A cozy living area is highlighted by a red accent wall and brick details. A comfortable blue sofa faces a mounted television, with a striped chair nearby. A mirror and decorative plant are positioned against a stylish cabinet, complementing the space's inviting layout.
Apartment in Lake View
4.83 out of 5 average rating, 484 reviews

Lakeview Charmer -with parking!

Walk to Wrigley 4 blocks away: 15 min walk; 3 minute drive. Walk to The Vic (around the corner), the lake, several theaters, many restaurants, RedLine el (1 block) takes you north to Evanston, south to Loop, to Sox. Park your car behind the building. A Garden 2 BR (one semi-private; see pics) with 2 queen beds. With rollaway and couch, could accommodate up to 6. We also have a fold up crib. FYI: NO Smoking inside or on the patio. No animals. See pic on patio: el is a few doors west.

Guest favourite
Apartment in Lake View
4.77 out of 5 average rating, 637 reviews

Cozy 2 Bedroom in heart of Lakeview

My place is close to Schuba's, Starbucks, Ann Sather's, Music Box, easy walk to Wrigley field, public transportation, and Divy bike rental. You’ll love my place because of its comfortable and convenient location! My place is good for up to four people (Not ADA.). Parking - It is free to park on the street in front of the building (N Southport) and various side streets. Please check street signs and parking meters. There are zone 383 parking permits if required in the kitchen drawer

Top guest favourite
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.
Apartment in Lake View
5 out of 5 average rating, 117 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.

Top guest favourite
A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.
Loft in Lake View
4.96 out of 5 average rating, 563 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.

Top guest favourite
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.
Apartment in Lake View
5 out of 5 average rating, 348 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.

Top guest favourite
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.
Apartment in Lake View
4.97 out of 5 average rating, 432 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.

Top guest favourite
Home in Wrigleyville
4.99 out of 5 average rating, 142 reviews

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

Top guest favourite
A bright living area features large bay windows with natural light filtering through. A white sofa is complemented by decorative pillows and a coffee table adorned with flowers. A mirror adorns the wall, enhancing the sense of space and light.
Apartment in Lake View
4.93 out of 5 average rating, 251 reviews

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Top guest favourite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Apartment in Lake View
4.94 out of 5 average rating, 163 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!

Top guest favourite
An inviting living area showcases a light-colored sectional sofa paired with a matching ottoman. A dark coffee table sits nearby, and a warm area rug lies underfoot. A bookshelf filled with books lines the wall, while soft lighting highlights the natural warmth of the wood flooring.
Home in Lake View
4.93 out of 5 average rating, 166 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.

Popular amenities for Lake View vacation rentals

When is the best time to visit Lake View?

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Quick stats about vacation rentals in Lake View

  • Total vacation rentals

    Explore 650 vacation rentals in Lake View

  • Nightly prices starting at

    Lake View vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 54,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    340 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 240 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    400 properties have a dedicated workspace

  • Wifi availability

    640 of Lake View vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Lake View rentals

  • 4.8 Average rating

    Lake View stays are highly rated by guests—averaging 4.8 out of 5!

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