Private suite holiday rentals in West Side

4.99 out of 5 average rating, 132 reviews

Cozy Hideout in Art Filled Chicago Neighborhood

Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

4.96 out of 5 average rating, 353 reviews

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.

Superhost

4.79 out of 5 average rating, 192 reviews

Alewyfe Farm Urban Garden Oasis- free parking!

Stay with us at the Alewyfe Inn- a cozy bohemian garden apt on the 1st floor of an 1880's brick cottage. Charming details, stocked pantry & coffee/tea bar in the kitchenette, your own private bathroom & entrances, & HEPA/UV filter. Enjoy the front yard permaculture garden with chickens, a firepit, & BBQ! 2 blks. from Pink Line/CTA, Lagunitas, Cinespace, St. Anthony & Mt Sinai hospitals, & a view of Douglas Park. 3.5 mi to Loop... Free street parking right out front is almost always available!

Superhost

4.83 out of 5 average rating, 170 reviews

West Loop 2 bedroom with outdoor space

2 bedroom 1 king and 1 queen / 1 bath condo in 2 unit building (we have 2 rollaway twins for additional beds) located 1/2 block from Union Park, if you aren't familiar with the area Union Park ends Randolph AKA Randolph Row with several Michelin Restaurants like Little Goat or Smyth either on or 1 block from Randolph. 2 1/2 blocks to the green pink line or 1/2 mile to the Rush/UIC Medical District. Everything you need for full access to the city. This is the top floor of a 2 unit building.

4.97 out of 5 average rating, 297 reviews

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!

4.98 out of 5 average rating, 161 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

4.93 out of 5 average rating, 385 reviews

Luxe, Private Suite w/Own Entrance-2023 Renovated

Newly remodeled private city oasis! Professionally designed cozy 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, DePaul, Zoo, Lincoln Pk, Wrigley, United Ctr, Lakefront.

4.89 out of 5 average rating, 112 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

4.94 out of 5 average rating, 136 reviews

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.

4.95 out of 5 average rating, 196 reviews

Bronzeville Beauty: Modern Style + Historic Charm

Come relax and take in Chicago's historic Bronzeville neighborhood. Stay in the bright and sunny garden unit of a fully renovated landmarked home built in 1887. We are located across from a neighborhood park with excellent access to CTA transit. Walkable to Lake Michigan, Lakefront Trail, White Sox stadium, IIT. Very close to McCormick Place, Hyde Park, and Chinatown. If you drive, free street parking is readily available in front of our home.

4.9 out of 5 average rating, 156 reviews

New Bright & Airy Entire Unit in Logan

This new modern unit is located in West Logan, one of the most exciting neighborhoods in Chicago. Close to public transportation, 2 blocks from the 606 Bloomingdale recreation trail, and minutes away from the best restaurants and bars in the city! Wifi, large-screen TV with streaming channels, washer/dryer, kitchenette, mini fridge, coffee/tea, board games, free street parking. You will love this custom designed & converted space!