Vacation rentals with outdoor seating in Des Plaines

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Top-rated outdoor seating rentals in Des Plaines

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Guest favorite

Guest suite in Pilsen Historic District

4.99 out of 5 average rating, 117 reviews

Cozy Hideout in Art Filled Chicago Neighborhood

Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

Guest favorite

Rental unit in Ukrainian Village

4.93 out of 5 average rating, 176 reviews

iKlektik House Chicago / BlueJay

Enjoy the warm heated floors and check out this home's amazing craftsmanship and artwork. Custom made built-in king size bed. Large custom kitchen, butcher block and claw foot tub in bathroom. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM The apartment is located in West Town. CLOSE TO THE UNITED CENTER New restaurants and neighborhood favorites, along with cocktail bars and music venues. Metra, Cta {buses and trains} close by. Metra: Western & Hubbard Free Street Parking Right Out Front!

Guest favorite

Home in Naperville

4.93 out of 5 average rating, 104 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs (w/ complimentary Hulu & Disney+), an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

Guest favorite

Rental unit in West Town

4.86 out of 5 average rating, 202 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #1

Entire 2 bedroom apartment in art-filled, Wicker Park building 5 min. Uber to downtown Chicago. Public transportation 3 blocks away. Restaurants, shops, parks, and nightlife within walking distance. Space includes -Brand new bathroom, walk in shower -1 bdrm w/ queen size bed - large closet -1 bdrm w/ single size bed, desk, shelf space -Pull out queen size couch bed -Fully equipped kitchen -AC -Personal back porch -Beautiful garden w/ outdoor furniture -1 parking space included + parking passes

Superhost

Rental unit in Chicago

4.84 out of 5 average rating, 273 reviews

4BDRM Gorgeous Apt Pilsen Private Prking Available

Stylish Retreat for Groups in Vibrant Pilsen Welcome to our 7-room home in lively Pilsen, perfect for families and groups of up to 10. Enjoy spacious comfort in a prime location. Explore vibrant murals, visit Simone's bar, and savor Sunday brunch at Dusek's. Catch a concert at Thalia Hall or sing at nearby karaoke or grab dim sum. Conveniently located just down the street from Chinatown and close to McCormick Place. Ideal for conventions and city adventures. Book now for an unforgettable stay!

Guest favorite

Condo in West Town

4.94 out of 5 average rating, 136 reviews

711 The Penthouse

Luxurious upscale Duplex Penthouse-River West neighborhood in downtown Chicago! Newly rehabbed and updated interior design that is mind blowing. Over 5600 sq ft. Features 5 bedrooms, 2.5 baths, 3 largeTVs with sonos sound system, game room!!. Near CTA Blue Line, close to the best dining and attractions of Chicago! Two large living areas perfect for hosting small events, bachelor(ette) parties, bridal or baby showers, work/travel, and family reunions. Rooftop with beautiful view of the skyline!

Guest favorite

Home in South Elgin

4.91 out of 5 average rating, 230 reviews

Riverfront rental with fun activity

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

Guest favorite

Rental unit in Wicker Park

4.95 out of 5 average rating, 131 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Guest favorite

Home in Wrigleyville

4.91 out of 5 average rating, 172 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Guest favorite

Condo in Wicker Park

4.94 out of 5 average rating, 131 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this prime, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Superhost

Rental unit in Evanston

4.82 out of 5 average rating, 167 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

Superhost

Rental unit in Berwyn

4.9 out of 5 average rating, 235 reviews

Family Friendly, 20 min train ride to downtown.

The perfect jumping off point for exploring Chicago, we are located in hidden gem Berwyn, just 2 blocks from the train station. Child-friendly, free parking. Our home is also the site of a micro-flower farm, with pocket forest, native garden, fruit trees and kids play house. Our first floor apartment also has a crib, high chair, bunkbeds and free street parking.