Holiday rentals in Northwest Side

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

LairBnB - Garden Apartment

*Pls Read ‘other details’ before booking* Welcome to LairBnB! This is a private garden unit with separate egress in our home near 6 corners in Portage Park. Ceiling height is 76”. Guests under 6' will be most comfortable here. We are old school Airbnb SuperHosts who love to host adult travelers in town for work or events in Chicago. We are steps away from Milwaukee, Cicero, and Irving Park bus stops, 8 minute walk to the Grayland Metra stop, and 20 minute walk to Irving Park Blue line & Metra

Roomy Retreat | Easy Parking | Walk to Train

Light-Filled Apartment | 20 Min Downtown | O’Hare ✔ Free Street Parking ✔ Fully-Equipped Kitchen ✔ Friends/Couples/Families ✔ Walk to Cafés & Restaurants ✔ No Stairs Perfect for friends and families, our home offers easy access to sightseeing while embracing the charm of a vibrant, walkable neighborhood. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleaning

Betty BnB

Free admission to The World's Smallest Betty White Museum! Oh, and a comfortable king-sized bed in a newly updated studio apartment. Centrally located in Oak Park, close to cafes and transit. Quiet, friendly neighborhood with ample street parking and a pub across the street. This is a basement unit with a kitchenette (NO STOVE/OVEN), cozy TV room, desk nook, and full bathroom. The bed is king-sized and has a firm mattress. The floors slope and there's no thermostat, but it's cute + welcoming

Cozy & Bright Townhome near O’hare -Self Check In-

Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

Top Floor Portage Park Lookout

Welcome to our bright, and spacious top floor apartment in Chicago. Enjoy the park vibes while being centrally located to all that the city offers. Just minutes away from O'hare airport and public transportation, enjoy exploring Chicago's downtown and the hip shops, dining, and culture in surrounding neighborhoods like Avondale and Logan Square. Stylishly decorated, our open-concept space offers a large bedroom and a fully equipped kitchen. Book now for a perfect Chicago experience!

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.

Chic Attic Stay | Logan Sq

Enjoy a stylish experience at this centrally-located place. Welcome to your private attic retreat near the heart of Logan Square, one of the most vibrant Chicago neighborhoods! About a mile away from the 606 trail, this thoughtfully designed place offers cozy charm— perfect for couples, solo travelers, or remote workers. What you’ll love: Fully equipped kitchenette Games & Entertainment (Connect 4 and Pac-man) Fireplace heater Easy access to transit

Studio Suite w/ FREE Garage Parking

Welcome to The Lazy House! We've created this completely private, studio-style suite to be your peaceful, cozy home base right here in Chicago's Irving Park neighborhood. This is the perfect spot for anyone who values independence, whether you’re a solo traveler, a couple, or a business guest. Unlike a typical private room, the entire top floor of our duplex is dedicated to you, providing a 100% private experience with absolutely NO shared indoor spaces

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.

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!

Bright Apartment

Relax in this sunny one-bedroom garden apartment in Albany Park (Not recommended for taller than 6'3"). Our apartment is perfectly located between downtown Chicago & O'Hare airport. You can go just about anywhere in the city in about 20-30 min as we are 5 minutes away from the Montrose blue line train stop, Kimball brown line train stop, and the I90/94 interstate. Please note, some areas have lower soffit ceilings.