Holiday rentals with a patio in Near North Side, Chicago

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

Floresitas Oasis, your home in Chicago

Welcome to Floresitas Oasis! A place where you and your guests can relax in the comfort of your own home! You will be close to the best restaurants, night scene, and near all of what Chicago and Pilsen has to offer when you stay at this centrally-located place. ***IMPORTANT NOTE*** When booking, please list the total number of guests that will be staying during your time with us. Any additional guests not originally in the inquiry will be charged an extra $100 per guest, per day.

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

The Sunshine Spot

Relax with the whole family at this peaceful place to stay. Centrally located off I-355 and I-55 major highways . Within walking distance from Promenade Mall ( over 30 plus stores , bars , restaurants ) . Also only about 30 minutes from Chicago. This 3 bedroom ranch has a two car attached garage with private entry ( very safe ) and a huge backyard with Grill . Very spacious and clean ! Thanks and look forward to seeing you at the Sunshine Spot !

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.