Apartment vacation rentals in North Side

Spacious 3BR with Parking Option, Steps to Metra!

Newly renovated, the Greenleaf is the entire second floor of a two-flat on a residential street. It has been thoughtfully designed for comfort and convenience. Great location for Loyola and Northwestern University visits or downtown sight-seeing. The Metra stop for trains to the Loop or the North Shore suburbs is ON OUR BLOCK. Lake Michigan free beaches are a mile away. Easy walk to a variety of small restaurants or 10-minute drive to Evanston or Andersonville for amazing dining and shopping.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

Clean, Bright Chicago Apt in Bucktown/Logan Square

The whole group will enjoy easy access to everything from this centrally located place. The Western Blue line stop that takes you to downtown Chicago is 2 blocks away. Downtown is a 15 minute ride away if you decide to rent a car. This is the only apartment in the building and sits right above the BEST Grilled Chicken restaurant in Chicago. The apartment is walking distance to many delicious restaurants and local coffee shops. You can find some of the best food in Chicago just steps away.

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

An elegant Chicago Northside Getaway

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Cozy Jefferson Park 2BR Apt

A lovely 2nd floor apartment flooded with natural light in a 2-unit building located in Jefferson Park. Conveniently located near O’hare airport, filled with small businesses, dive bars, and family-owned restaurants. Downtown Chicago will take 20-40 minutes, depending on traffic. My partner and I live in the unit below and can answer any questions you may have throughout your stay. We have created a warm and safe place for all to feel welcome!

Designer 3br with Balcony & Elevator on Clark!

My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago - You'll love the neighborhood - its vibrant food and arts scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city - if work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable.

Beautiful, sunny 2nd floor 3BR/1BA w free parking

Sunny second floor 3Br/1Ba apartment in the tree-lined, walkable neighborhood of Lincoln Square. Updated apartment with original woodwork offers easy access to Wrigley Field (7 el stops), Lake Michigan beaches, and downtown Chicago. Free parking space included, close to Western brown line el station and Lincoln Square's many restaurants and shops. Old Town School of Folk Music is a 5-minute walk. 2 miles to beaches.

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

You’ll love my place because of the privacy, comfort, first-floor convenient access (no stairs), no clutter, the ambiance, the neighborhood, free on-street parking, and your host (conveniently living in a separate apartment on the second floor). My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).