Holiday rentals in North Side

A+Chicago Roscoe Village Entire Home Wrigley+ More

Elegant large bright posh eclectic flat in heart of Roscoe Village very comfortably furnished to enjoy charismatic Chicago. Free parking. Very fast internet and laptop comfortable space for your home office. Professionally cleaned, well appointed cozy, perfect for families or a solo traveler. Fab decor, fully stocked kitchen plus all amenities and an open-plan layout invites you to enjoy quiet elegant comfort of home. Easy walk to Wrigley Field. Take the bus or train downtown. Easy walk to wine & dine in posh areas of Roscoe Village, Lake view & Lincoln Square. Or a quick drive to downtown! This is A FULL UPPER FLOOR, and NOT a Garden Basement. You are a short walk away from restaurants, stores but stay in a quiet beautifully appointed 1100 square feet elegant 1 large Bedroom flat with parking all to yourself. Enjoy this -its hard to find in this city. Refurbished to the highest standards this spacious apartment is located moments from shopping, restaurants and pubs in the heart of cool Roscoe Village Lakeview & Lincoln square neighborhoods of Chicago. Famously eclectic and vibrant, we are the heart of Chicago's best offerings. Boyztown, Buck town, Lincoln park or music at Scubas, Stage 777, Revolution Brewery, and other cool hip spots are a short walk or ride away. Home of the CUBS -Chicago’s best attractions "Walking to Wrigley field with all of the other "fans" singing GO CUBS was a fab experience" a guest's comment. The most difficult decision of the day might well be whether to eat out - many restaurants, pubs and bars in the area catering for all tastes and pockets; or to stay in and cook - cozy comfort of a first class home. We are keen for you to enjoy your stay with us, and we will do our best to make your stay a memorable one. The accommodation is the whole upper floor, (one short flight of stairs) and you have your own entrance. Enjoy a luxurious home away from home. You have an entire floor to yourself with 100% privacy. Interaction with our guest is as much or as little as you need, when we are in town. We often travel, but always have a caretaker who will be responsible to ensure satisfaction for your complete stay. Part of the area's charm is not only the elegant vintage Chicago style homes, or how easy it is to walk to all the local favorite dining, but how much personality all the small independent businesses on Roscoe street have. This gives the neighborhood a hip vibe and friendly, small-town feel! Centrally located in the middle of Wrigleville, Lakeview, Bucktown, Logan Square, Lincoln Square and 10 minutes to train station - 5 minutes to bus or divvy bikes. Or park your car FREE - a luxury in Chicago Centrally located, yet quiet and charming you will be within minutes of everything this mega city has to offer. Chicago is a major city second only to New York, in the United States, and is a global alpha city with fantastic offerings. This glittering city built on the shores of Lake Michigan is where you’ll find some of the biggest and best entertainment outside of New York City and Las Vegas, including touring Broadway shows, professional sports teams, stand-up comedy and concert venues – including the iconic Chicago Theater and Grant Park, home of Lollapalooza. The second city is also home to year-round attractions and world-class museums – the Field Museum, the Skydeck at the Willis Tower, Shedd Aquarium, and the Art Institute of Chicago. Chicago sports fans fuel their passion year-round as they cheer on the north side Cubs or south side White Sox in the summer, Bulls and Blackhawks in the winter, and Bears in the fall.

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

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

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.

Stylish Studio in Historic Logan Square

Modern garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom and kitchenette is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a magical shared backyard space. The owner's treehouse deck can be reserved. An oasis in the city with exciting city easily accessible!

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.

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

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!

City life oasis, Chicago’s North Side

Irving Park is one of Chicago’s great neighborhoods! Close to everything including WrigleyField, 10 minutes away. There’s so much to do, like walk to Mcfetridge park district that has indoor Ice rink and outdoor swimming pool. You can hop on the blue line train to down town or just enjoy this newly remodeled, classic home! Classic clean decor with White tiger in the dinning room. Always keeping it fun and interesting!