Holiday rentals with a fire pit in North Side

4.9 out of 5 average rating, 528 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

4.97 out of 5 average rating, 153 reviews

Home in Wilmette

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

4.97 out of 5 average rating, 154 reviews

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

4.99 out of 5 average rating, 146 reviews

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at Retro Modern Bungalow—the perfect pad for up to 4 friends. Featuring two spacious bedrooms, each with a king bed and luxury linens, a propane fire pit and a fully fenced [pup-friendly] back yard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

4.98 out of 5 average rating, 155 reviews

Guest suite in Chicago

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*

4.97 out of 5 average rating, 112 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

4.97 out of 5 average rating, 294 reviews

Guest suite in Chicago

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!

4.95 out of 5 average rating, 127 reviews

BRAND NEW Elegant Renovation in Bucktown (Chicago)

Elegant, newly renovated 1 bedroom apartment nestled in the trendy Chicago neighborhood of Bucktown. Our home is the perfect place for you to stay while you explore the city. Located just a few blocks away from vibrant Bucktown restaurants, live music, bars, 606 city trail, and downtown. The Damen blue line subway station is about 10 minute walk from the apartment, giving guests easy access to O’Hare and the rest of the city. Free street parking is also available.

4.87 out of 5 average rating, 105 reviews

McCormick 2B/2Ba corner unit/opt parking/sleeps 6

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • 2 Queen size beds + Sofa bed for 2 extra guests • Comfortable stay for up to 6 guests at a time • Access to the Gym in the building • Fast dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

4.94 out of 5 average rating, 127 reviews

Guest suite in Chicago

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.

4.96 out of 5 average rating, 275 reviews

Super clean and family-friendly 3-bdrm entire apt

Live like a local in this classic Chicago two-flat apartment (aka Hamlin House), built in 1908. The living area features beautifully restored hardwood floors and a recently rehabbed bathroom. We want you to feel at home in Logan Square! The unit has a kitchen full of utensils, cookware, and enough serveware for entertaining. We are around to answer any questions and help you navigate the area. Perfect for families, friends, and short or extended stays.

4.95 out of 5 average rating, 699 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

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Popular amenities for North Side Holiday Accommodation with Fire Pit

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fire pit

4.83 out of 5 average rating, 100 reviews

Home in Bensenville

Skyway w/ Shuffleboard

HeatherRating, 5 stars1 month ago

Wonderful house for our group of 10 ladies! Blaine was great and prompt with all communication. Would definitely stay again and recommend to others

4.96 out of 5 average rating, 123 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

KristenRating, 5 stars2 days ago

Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!

4.89 out of 5 average rating, 174 reviews

Lake View | Wrigley Designer House w/Patio

AmyRating, 5 stars2 weeks ago

We had a great stay! Super comfortable, lots of room and great location. Host was quick to respond to questions and helpful. It was perfect for our girls trip (party of 6). Book it!

4.95 out of 5 average rating, 398 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

CarmenRating, 5 stars1 week ago

One of the best Airbnbs I have stayed at. It was beautifully decorated and super clean. Had everything I needed to feel comfortable and at home. The host was extremely responsive. The parking was a bit difficult but would not deter me from staying there again. Very close to downtown, about 10 minutes. Highly recommend.

4.86 out of 5 average rating, 139 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

ShaniaRating, 5 stars2 weeks ago

I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!

4.85 out of 5 average rating, 126 reviews

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

MicahRating, 5 stars1 week ago

Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.

4.95 out of 5 average rating, 152 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars3 weeks ago

Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!

4.93 out of 5 average rating, 107 reviews

Beautiful Chicago Greystone

RoxanaRating, 5 stars2 weeks ago

Great place to accommodate a big group. Close enough to the city if you don’t want to be in the heart of the city. Responsive host

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Apartment rentals with a fire pit

4.92 out of 5 average rating, 197 reviews

iKlektik House Chicago / BlueJay

ARating, 5 stars2 weeks ago

We really enjoyed our stay here! Perfect for two people. This place is really cute and unique. Love the decor and seeing all the cool art projects. This place was within a couple miles of all the places we wanted to see, especially Soldier Field, so a Uber/taxi ride was cheap and very convenient. Super cute neighborhood too with beautiful row houses both modern and original. It is a nice quiet neighborhood as well and we felt very safe! We would recommend the Iklektik/Blue Jay house to anyone visiting Chicago that wants a comfortable and cozy experience!

4.88 out of 5 average rating, 120 reviews

Garden Oasis

KenlyRating, 5 stars2 weeks ago

Susan was a fantastic host with great communication and super friendly! The place is in a great neighborhood that’s safe and walkable to many restaurants and bars. Easy street parking was also a perk! Would definitely stay here again in the future!

4.97 out of 5 average rating, 123 reviews

Stylish 2BR stunner w/ unbeatable location

KathleenRating, 5 stars6 days ago

We had the absolute best experience staying at Eric’s place in Ukrainian Village. The parking was a huge plus, it was walkable and felt so safe and charming! The space was stunning and matched the listing perfectly. Will definitely be staying here next time we come to Chicago!

4.99 out of 5 average rating, 156 reviews

Apartment in Forest Park

Sunny 1 bedroom apartment 1 block from restaurants

EleanorRating, 5 stars1 week ago

Jim was a fantastic host. Very responsive and timely in his communications and support for our needs during our stay in their place. Their home was comfortable and well appointed with additional amenities you don't often see in AirBnB spaces, like N'espresso appliances and supplies. We would definitely consider repeat visits! Thank you, Jim!

4.86 out of 5 average rating, 113 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

DeniseRating, 5 stars2 weeks ago

I loved everything about my stay ! Very nice and clean and the host were amazing

4.84 out of 5 average rating, 101 reviews

Charming retreat w/ fireplace

BriRating, 5 stars2 weeks ago

We truly had the best time staying at Alec’s. The space is lovely, comfortable, and has everything you’d need. The outdoor spaces were beautiful and private with a high fence surrounding it. We enjoyed spending time by the fire and the neighborhood is great. Our favorite part by far were Alec’s two lovely pups Molcajete and Lobita. They were absolute ANGELS and made us so happy- we hated leaving them. Alec was a great host- super communicative, friendly, and just what we needed. When we come back to Chicago, we’ll definitely stay with him again.

4.97 out of 5 average rating, 310 reviews

Apartment in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

PatriciaRating, 5 stars3 days ago

5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!