Vacation rentals with outdoor seating in Norwood Park

Modern LOFT Ukrainian Village 2nd floor

Private, Bright 2nd floor Loft with Tall Ceilings with Lots of Light. Creative Decor with Artwork and Artifacts. Relaxing and Cozy. Tree Top View of the Garden. Everything you need for a Long or Short Time Stays. Stocked Kitchenette, Modern Bath, Laundry and Fast WI-FI . Perfect for 1 or 2 for work or play. The Street is Quiet, Conveniently Located just 1 block from Bustling Division Street in Wicker Park, Downtown, the Blueline to all Airports and 1 Mile from the New Salt Shed Music 🎵 Venue

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

Spacious and Cozy 3BR Apt Near ORD / Metra

Welcome to our charming and cozy apartment. This apartment is designed to be your home away from home in Chicago. From the moment you step inside you will be captivated by the tasteful decor and attention to detail. The apartment is located in a great neighborhood close to public transit and highways. Also, you will find plenty of restaurants, cafes, shop, and entertainment options nearby. Our apartment offers a comfortable and inviting atmosphere perfect for your next vacation or business trip.

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

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

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.

King Bed, Huge Spa Shower, Dining Destination

This home was designed with love! Inspired by our favorite boutique hotels - nestled on a tree-lined street in Logan Square, a locals-only destination for brunch, coffee, craft beer and cocktails. Relax in the massive custom steam shower or catch up on HBO on the 50” WiFi TV. Luxe details throughout -premium espresso, memory foam beds and upgraded Italian linens, lots of outlets, and a fully-equipped kitchen. Easy parking, a rarity in the city. Central location- Quick walk to Blue Line Train

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

Cozy Hidden Gem Near Downtown+Train+Dining+Parking

Experience one of the best neighborhoods in Chicago in this Hidden City Gem, 2BR/1bath apartment. Perfect for couples, families, or small groups. Centrally located, just minutes to downtown, CTA/L Pink Line train is one block away, Free WiFi, permit parking, cable, in-unit front load washer/dryer, highways nearby. Explore the vibrant community, art/murals, delicious food, and cultural venues. Book now for a comfortable and memorable stay in the Heart of Chicago Pilsen Neighborhood.

The Vanderpool House

The Vanderpool House has a Private Suite in a historic 100 year old Chicago Bungalow just 2 blocks away from the 2nd largest transit center in Chicago. The Blue Line L stop will take you downtown, the airport, or the Rosemont Convention Center. The Metra train will take you downtown or the northwest suburbs and you have 13 bus lines will take you anywhere else. Onsite parking is available at no extra charge. Theaters, Neighborhood Restaurants, Art Museums within walking distance.

Right in the heart of Logan Square.

BEST LOCATION IN LOGAN SQUARE!! Brand new stylish 3 bed, located in the heart of the highly desirable Logan Square neighborhood. This luxurious space is situated right by the historic Logan Square Boulevard, literally 10 STEPS AWAY from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

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