Private suite holiday rentals in Chicago

Cozy 1BR + Futon • Deck • Laundry • Private Entry

Located at the geographic center of Chicago with plenty of FREE street parking. The area is very safe and about a 10-min walk to the 35th/Archer Orange Line and just 3 blocks from the Archer bus—both take you downtown within minutes. This lower-level 1BR has a private entrance, spacious queen bedroom, living room with full futon, full kitchen, and private bath. Perfect for solo stays, couples, small families, or work trips. Enjoy your own space with access to a back patio, grill, and laundry.

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

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

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

A space crafted for comfort and intentional stays.

A calm, light‑filled suite in the heart of Pilsen, made for comfort and staying with intention. A kitchen built for everyday cooking. Fast Wi‑Fi. A dedicated workspace built for long days of focus. The bedroom stays calm and dark. The living area holds your everyday routines. The art throughout adds warmth and character. Walkable to cafés, the Pink Line, the Medical District, and McCormick Place. Made for travel nurses, remote workers, creatives, and anyone settling in for more than a weekend.

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

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.

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.

Cozy and Private Andersonville Retro Studio

In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

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).

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.