Holiday rentals in North Side

4.96 out of 5 average rating, 114 reviews

Apartment in Chicago

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 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. Free parking on Lawndale Ave.

4.94 out of 5 average rating, 419 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

4.99 out of 5 average rating, 363 reviews

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

4.96 out of 5 average rating, 172 reviews

Home in Chicago

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.94 out of 5 average rating, 248 reviews

Norwood Park Gem, Chicago: Driveway Parking

Experience the charm & comfort of our light-filled one-bedroom apartment in beautiful Norwood Park. Located just above our home, this cozy retreat features a comfy king bed and central A/C, ensuring your stay is as comfortable as possible. Perfectly situated, we're only 0.1 miles from Starbucks and less than 0.5 miles from numerous local restaurants. We’re outside the hustle & bustle of busier neighborhoods, but close to the expressway, Metra and Blue line. Plus, convenient driveway parking!

4.97 out of 5 average rating, 159 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

4.98 out of 5 average rating, 154 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*

4.87 out of 5 average rating, 127 reviews

Apartment in Chicago

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

4.93 out of 5 average rating, 126 reviews

Logan Square Garden Sanctuary

This house is located in historic Logan Square. The space is a newly renovated basement unit of an owner-occupied two-flat. It's right next to Palmer Square which is a two acre park with a jogging path, kids area, and benches. It's a perfect place to have a picnic or meet with friends. The neighborhood is very walking-friendly and there's tons of great shops and restaurants in the area. The unit has an open floor-plan with a comfy memory foam bed, futon, a full bathroom, and kitchenette.

Superhost

4.86 out of 5 average rating, 361 reviews

Renovated Designer Flat in Heart of Lincoln Square

Kick back with a fresh coffee and enjoy the designer touches of this renovated apartment, including marble worktops, wood floors and 1920s exposed brickwork. There are great courtyard views, while the memory foam mattress and super-sized sofa add real comfort. Lincoln Square is a quaint, family-friendly neighborhood. There's abundant German influence here, and great shops, restaurants, and bars line Lincoln Avenue. Downtown is 20 mins by train. Wrigley Field is close too.

4.94 out of 5 average rating, 161 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

4.94 out of 5 average rating, 125 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.

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Popular amenities for North Side holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in North Side

4.86 out of 5 average rating, 65 reviews

Cushy pad fully remodeled 10 min from O’Hare.

JaemondRating, 5 stars2 weeks ago

Great place an host, will book again whenever I’m back in Chicago.

5 out of 5 average rating, 132 reviews

Easily accessible Uptown room

MarinaRating, 5 stars1 week ago

We absolutely loved starting at Cameron’s place! It was so clean, beautiful and in the perfect location for us. Cameron was so kind and helpful and really set the bar for what an Airbnb host should be. We would definitely book to stay there again!

5 out of 5 average rating, 10 reviews

Extended Stay Large Studio:New Stylish, Affordable

DarrielRating, 5 stars4 days ago

This place is a 5 star in various areas. The place is spacious, new, clean and safe. The host is great. They take great care of those who book with them. Sometimes it’s hard to find great hosts who treat you the way that they want to be treated. They are a perfect example. They pay attention to the details. My stay was enjoyable and will book again. This was my second stay.

4.97 out of 5 average rating, 269 reviews

At the crossroads of comfort and care

SalmanRating, 5 stars2 weeks ago

We had a wonderful stay at William’s Airbnb! He was very friendly and welcoming, making us feel right at home from the moment we arrived. The house was spotless and well-maintained, with great amenities that made our stay comfortable. The location is fantastic—just a short walk to Devon Avenue, where you’ll find plenty of amazing restaurants. Highly recommend staying here!

4.77 out of 5 average rating, 318 reviews

Chicago River Room near USMLE

JessicaRating, 5 stars2 months ago

Mary's place was a great location for our short trip to Chicago! It was a short Uber drive from the airport, and a short drive to the All-State Arena. We did arrive late at night due to flight delays and opted for an Uber versus the train. I am glad we did cause it seems like the train station is under construction for the side we needed and would have been a bit more of a walk departing from the other side, but definitely not a dealbreaker or anything. The house is a short walk from this breakfast place that we actually went to twice during our short stay, with other options nearby. Overall, the house felt cozy and clean, but we did struggle with getting in the bathroom first thing in the morning with the other guests in the house during our stay. Mary was very responsive and a great host to us during our stay. The bed was comfortable as well and the room had amble space for a large suitcase, a carry-on, and two large bags with space to spare for two people.

4.93 out of 5 average rating, 101 reviews

Edgebrook bdr by golf course

JaneRating, 5 stars1 week ago

Jefferson is hands down one of the most fantastic hosts I've ever stayed with! He was extremely communicative, welcoming and warm, and a brilliant human being! The day of my arrival, Jefferson offered me to attend a candlelight performance of his string quartet, Metropolis String Quartet; and it was an absolutely phenomenal experience! He gave me an incredible restaurant recommendation for Longman and Eagle after the performance and it was a superb gastronomic experience. His place is lovely, quiet, and clean. A Whole Foods is about a 13 min walk from his home, and so is a great pho restaurant for a tasty lunch. Jeff also showed me the Chicago Botanic Gardens and later, we enjoyed charcuterie in his back yard and whisky tasting. Jeff has a spectacular whisky collection and I highly recommend you book a tasting with him and purchase one of the rare whiskies and scotches he has in his collection. :) Based on reviews, I knew Jeff was going to be a great host--he exceeded my expectations.

Apartment in Chicago

4.75 out of 5 average rating, 4 reviews

Chic Chicago Spa Retreat – Luxe & Light-Filled

IrinaRating, 5 stars2 weeks ago

The place is just perfect . I think that the host hired a designer or maybe he has such a great taste but the remodeling , furniture and decor .. well just awesome . We only had problem with parking but 5 min from the place we found plenty of parking . Enjoy . P.S. The bathroom was very nice. My favorite place in the apartment I would add warm robes in there . :)