Vacation 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.

Priv. BR/BA in French Bungalow - Near Lincoln Sq.

This 102-year-old French bungalow home is located in Lincoln Square West within walking distance to the popular Lincoln Square Chicago neighborhood. The CTA Brown Line to downtown Chicago is also within walking distance. Divvy bikes are available nearby for a bike ride down to Lake Michigan as weather permits. Guests of all backgrounds are welcome to stay in a newly furnished private bedroom with a private bathroom. The kitchen, living room, and a sunroom porch are all accessible to guests.

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

Montrose Gardens

Nestled in the heart of one of Chicago’s most diverse neighborhoods, our garden unit offers a space to stay back and relax, while maintaining a short commute to all areas of the city. Minutes from the blue line, 20minutes from the lake, downtown, the united center, wrigley; we find ourselves in a truly great location. On-site parking, pet friendly, and a private outdoor area for the airbnb. Hosts are right above if you have any questions or need a recommendation!

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

05a. Common Room King

We have a King-sized bed in a Common Room. This is in a shared common room space. Up to 3 other guests my be booked in this room. The room has limited storage and NO DOOR. This space is best for those with little to no bags. Breakfast is included in your stay. We keep the pantry stocked with eggs, bacon, milk, orange juice, jam, bread, fruit, pancake mix, coffee and tea. Any of these items can be used to make yourself breakfast in the morning.

Lovely Bedroom 3 in a New Renovated Apartment

This is one of two rooms in my apartment that listed on AirBnB. There is one bathroom to be shared with other guests. My home is midway between O'Hare Airport and Downtown Chicago in a safe and quiet neighborhood. It's very convenient whether you drive or use public transportation (20 minutes to O'Hare, 25 to the Loop on Blue Line, CTA and Metra train stations are 3 blocks away). This is on the second floor and there is no elevator.

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.

Loft Style Private Apt 2 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Top-Floor 1BR | Steps to Train + Free Parking

Cozy top-floor 1BR with modern finishes, new bathroom, and a super comfy bed. Only a 6-minute walk to the Blue Line for easy access to downtown and O’Hare. Quiet neighborhood, 3 blocks from Logan Square’s best coffee, dining, and nightlife. Fast Wi-Fi, dedicated workspace, laundry in building, free street parking, plus early check-in/late check-out when available.

Feelin’ Nauti Near Wrigley

I took a perfectly nice little flat on a beautiful street and filled it with great things...I want my guests to feel less like they are at an Airbnb and more like their 'very tidy but quirky friend' gave them keys to the flat for a weekend away. Super easy access to Wrigley Field, the bustling Southport shopping corridor, and all of the 'Boystown' nightlife.