
Holiday rentals with outdoor seating in Northwest Side
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Northwest Side
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Walk to Oak Park from a Bright Madison Street Loft
Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

Peaceful Portage Park Apartment
You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

Balcony • Free Parking • Near O’Hare + Transit
This upstairs 1‑bedroom apartment is your quiet, bright home base just 10 minutes from O’Hare Airport and near the Blue Line for easy city access. Enjoy a full kitchen, fast Wi‑Fi, king bed, and Smart TV for relaxing evenings. • Free driveway parking with notice • Private balcony seating • Dedicated workspace & fast Wi‑Fi • Hotel‑comfortable king bed + blackout curtains • Self‑check‑in + private entrance While there’s no in‑unit laundry, optional wash‑and‑fold service ($25/load) is available.

Gorgeous Studio 15 Minutes From Ohare!
Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

BnB on Grace Street - Modern 2-Bedroom Guest Suite
Welcome to Bnb on Grace Street in the charming Old Irving Park neighborhood, in one of the original homes built in 1893! Our private guest suite is modern and recently renovated while highlighting original features of the home such as the exposed brick walls. It's just 2 blocks from a major highway and from the El Train blue line, from which you can travel into downtown or out to O'Hare Airport. The suite includes 2 bedrooms, 1 bathroom, a kitchenette/dining area, and living room.

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Cozy guest studio, great for couples!
This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

The Logandale: HUGE Mid-Century Home, sleeps 15
Welcome to The Logandale! This 4 bed/3 bath mid-century modern home is ideal for families, professionals, and groups. Enjoy an open floor plan, private patio, game room, and bedrooms with memory foam mattresses. The fully-equipped kitchen, Smart TVs with Netflix, and a backyard fire pit ensure a comfortable stay. Located in the trendy Avondale/Logan Square, you're close to public transport, eateries, and attractions. Experience Chicago's best with us! 🌃🛏️🎮🔥

Funky & newly remodeled 1 bed in Hip Logan Square
Recently remodeled 1 bedroom garden apartment with a fun aesthetic in hip Logan Square. Walking distance to top bars, restaurants and coffee shops such as Sugarmoon, Park & Field, Best Intentions, Lou Malnatis, Damn Fine Coffee Bar and many more. Blocks from the 606 Trail, 90/94 & public transportation. Lovely shared front yard landscaped with florals + garden beds. We will pass along a welcome guide with a list of all our favorite places in the neighborhood!

Logan Square Garden Suite
Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

Northside Chicago Getaway
This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!

Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!
Popular amenities for Northwest Side outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Private 3rd Floor Apartment

Spacious 5-Bedroom Retreat in Forest Park

The Chicago River House – GIANT wall projector!

California Cottage/4br prime location Logan Square

Cool Quiet Coach House, Private Access + Patio

BoHo House - A Chic, 1903 Chicago Workers Cottage

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14
Apartment rentals with outdoor seating

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

NorthSide Chicago duplex 5-BD,2King size-free park

Simple, Comfortable Pilsen Apt w/ Artistic Touches

💙⚾️ 💙Great Apt, 3 miles West of Wrigley Field 💙⚾️💙

Logan Square 2nd Floor Chicago Victorian

Sunny 1 bedroom apartment 1 block from restaurants

5* City Oasis: Logan Square/Avondale Neighborhood

Ravenswood Guest House Annex
Condo rentals with outdoor seating

Inspired, luxe living in Logan Square on BLVD #1

NEW luxury Old Town 1-Bedroom condo

Logan Square Beauty with 2 Bedrooms W/parking

Can't Beat This 2min Walk to Wrigley!

Susie's Space. 2BR easy parking & pet friendly

Spacious 4 Bedroom Condo

Welcoming 2BR in Chicago's Best Neighborhood!

Designer Loft in Fulton Market with Parking
Destinations to explore
- Chicago Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Southern Indiana Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Rentals with a washing machine and dryer Northwest Side
- Rentals with a patio Northwest Side
- Condo rentals Northwest Side
- Fitness-friendly rentals Northwest Side
- Smoking-friendly rentals Northwest Side
- House rentals Northwest Side
- Rentals with a hot tub Northwest Side
- Rentals with an EV charger Northwest Side
- Family-friendly rentals Northwest Side
- Hotel rooms Northwest Side
- Rentals with breakfast Northwest Side
- Pet-friendly rentals Northwest Side
- Private suite rentals Northwest Side
- Rentals with a fireplace Northwest Side
- Apartment rentals Northwest Side
- Rentals with a fire pit Northwest Side
- Rentals with outdoor seating Cook County
- Rentals with outdoor seating Illinois
- Rentals with outdoor seating United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wilmot Mountain Ski Resort
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo




