Vacation rentals with outdoor seating in Lake View, Chicago

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Top-rated outdoor seating rentals in Lake View, Chicago

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Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 295 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

Oct 2 – 9

$122 per night

Guest favorite

Guest suite in Andersonville

4.96 out of 5 average rating, 320 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Dec 25 – Jan 1

$78 per night

Superhost

Apartment in Roscoe Village

4.9 out of 5 average rating, 372 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.

Nov 9 – 16

$152 per night

Guest favorite

Home in Lake View

4.98 out of 5 average rating, 206 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!

Dec 1 – 8

$138 per night

Guest favorite

Apartment in Lake View

4.97 out of 5 average rating, 244 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

Dec 8 – 15

$153 per night

Guest favorite

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!

Dec 3 – 10

$130 per night

Guest favorite

Guest suite in Lincoln Square

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Nov 7 – 14

$84 per night

Guest favorite

Apartment in Roscoe Village

4.96 out of 5 average rating, 238 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".,

Jan 14 – 21

$90 per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 176 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.

Sep 5 – 12

$132 per night

Guest favorite

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.

Jul 10 – 17

$109 per night

Guest favorite

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.

Oct 14 – 21

$118 per night

Guest favorite

Apartment in Lincoln Square

4.96 out of 5 average rating, 323 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Nov 18 – 25

$114 per night