Holiday rentals in North 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.

13 mins DT | 4 mins Lake | Elegant Style Loft

Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲𝗻 with modern appliances • 𝗦𝗺𝗮𝗿𝘁 𝗧𝗩 𝗮𝗻𝗱 𝗱𝗲𝗱𝗶𝗰𝗮𝘁𝗲𝗱 𝘄𝗼𝗿𝗸𝘀𝘁𝗮𝘁𝗶𝗼𝗻 — perfect for professionals or remote workers • In-unit washer/dryer and dishwasher for convenience • Rooftop area with breathtaking city views • Fitness center access to stay active during your stay • Steps from Montrose Beach, Aragon Ballroom, and Riviera Theatre • Parking available

NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance

Gorgeous, classic Chicago brownstone with a private entrance and private bath. It is your own private apartment with a private kitchenette, private en suite bath and a private entrance. In the heart of a great city with every amenity and over 500 five star reviews! Walk to Wrigley or ride one of our free bikes. This suite is located 5 minutes from the "el" and many restaurants, boutiques and taverns. TOP 1% of all Airbnbs in Chicago after a DECADE of helping our guests in every way we can.

Peaceful, Cozy 1Bed/1.5Bath Duplex w Free Parking

Welcome to Chicago’s Northside! Step into this Edgewater two-floor, 1.5 bathroom oasis on a quiet tree-lined street. Enjoy all the comforts of home with a well-equipped kitchen, 1.5 bathrooms (including full tub/shower), bedroom on the top floor, plus a 65” TV that is perfect for relaxing with a movie or streaming show. Floors connected via a charming spiral staircase. Reserved parking space in the building’s parking lot. Walking distance to Metra, Loyola, CTA red line, bakeries & coffee!

Luxury Chicago Apartment

This bright and comfy apartment gives you the best of both worlds—peaceful mornings and exciting nights. Just a short walk to Clark Street, you’ll have quick access to amazing restaurants, coffee shops, and nightlife. When you're ready to explore downtown, it's just a quick train ride or drive away. Inside, the space is warm, clean, and thoughtfully set up with everything you need to feel right at home. It’s the perfect spot for travelers looking to relax and recharge between adventures.

G3- Next to Downtown Best Location

Bedroom for rent in the desirable neighborhood of Lakeview. Location is its most important fact. It is right in front of one of the biggest supermarkets(Whole Foods). There are multiple stores just one block away such as target, xsport fitness, banks. Different restaurants and more. Walkable to brown line train to go downtown as well as bus stops to go all possible directions. Beautiful apartment, bedroom with closet. All you can think of at a great price. host lives in the same apt

Top Floor Portage Park Lookout

Welcome to our bright, and spacious top floor apartment in Chicago. Enjoy the park vibes while being centrally located to all that the city offers. Just minutes away from O'hare airport and public transportation, enjoy exploring Chicago's downtown and the hip shops, dining, and culture in surrounding neighborhoods like Avondale and Logan Square. Stylishly decorated, our open-concept space offers a large bedroom and a fully equipped kitchen. Book now for a perfect Chicago experience!

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.

Edgewater Arts & Crafts Retreat 2

You will find this a relaxing and comfortable base of operations for whatever you may wish to do in Chicago. The room & house are quiet & comfortable, offering the perfect place to spend a refreshing evening after the day's adventures, whatever they may be. The friendly & beautiful neighborhood is right near Lake Michigan, and offers excellent transportation options to the rest of the city. Chicago is a rich tapestry of opportunities and resources.

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

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.