Private suite holiday rentals in North Side

2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking

This 100% private apartment in the lower level is just minutes away from O'Hare, Rosemont, Allstate Arena, I90, & the CTA. About 30 minutes from downtown or Wrigley Field. This two-bedroom private apartment in a newly built single-family home has plenty of space in an open-concept living room, kitchen, & dining room for big families. You will have a separate private entrance, fast wi-fi, full kitchen, & laundry. You will have 1 queen bed, 4 twin beds, & 1 air bed. There is free street parking.

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Logan Square Chicago 2BR cottage, close to it all!

Beautifully restored 2 bed/ 1 bath apartment in a 100+ year old workman’s style cottage in the heart of Logan Square. Relax in your private first floor unit on a quiet tree-lined residential street. The living & dining rooms are furnished with brand new sofas & multiple vintage pieces perfect for spreading out & relaxing or cooking dinner in the updated kitchen. To keep costs down, a cleaning fee has already been included in the nightly rate. Excessive mess will result in an additional fee.

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Stylish Studio in Historic Logan Square

Modern garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom and kitchenette is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a magical shared backyard space. The owner's treehouse deck can be reserved. An oasis in the city with exciting city easily accessible!

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Level 2 EV charger available.

Luxe, Private Suite w/Own Entrance-2023 Renovated

Newly remodeled private city oasis! Professionally designed suite with private keyed courtyard entry & small lighted covered patio w/table and chairs (work outside!) New ensuite bathroom w/heated floor, bespoke vanity & fab water pressure. Quiet tree-lined street with free parking, great restaurants, old pubs, shops & transport walkable. Great launch to all Chicago has to offer while enjoying charming Bucktown. Close to Downtown, Wrigley, DePaul, Zoo, Lincoln Pk, United Ctr, Lakefront.

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

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. 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. This is a quiet, owner-occupied property best suited for travelers visiting Chicago. It’s not intended for gatherings or local stays.

Studio 15 Minutes From Ohare!

Please read through entire listing before booking. Enjoy a cozy, private, and spacious studio on a quiet, tree-lined street in Chicago’s Dunning neighborhood. You’ll have a full kitchen, bathroom, comfy living space, plus a large backyard and free parking. Perfect for couples or business travelers. Close to great restaurants and parks, Rosemont (10 min), O’Hare (15 min), and downtown (35–45 min; varies with traffic).

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!

Private Lincoln Square Garden Apt

Clean and comfortable one-bedroom garden apartment with kitchenette in the lower level of a vintage brick 2-flat building. Sleeps 2-4 comfortably (queen bed in bedroom and a pair of stackable twin beds in the main living area). Pleasant and lively neighborhood and a short walk to the train.