Holiday rentals with a fire pit in South Loop, Chicago

4.95 out of 5 average rating, 396 reviews

Home in Pilsen

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

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

Guest suite in Noble Square

4.96 out of 5 average rating, 344 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

5 out of 5 average rating, 4 reviews

The South Loop Suite

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

4.97 out of 5 average rating, 309 reviews

Flat in Cicero

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

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

4.99 out of 5 average rating, 145 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.

4.9 out of 5 average rating, 394 reviews

Loft in Little Italy

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

Apartment in Little Italy

4.94 out of 5 average rating, 208 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

5 out of 5 average rating, 9 reviews

South Loop | Rooftop With In & Out Parking | 1

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, two-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🔥 Rooftop Patio W/ BBQ 🏊‍♂️ Rooftop Pool 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🛏️ 2 Bedrooms | 2 Bathrooms 🛌 2 Queen Beds 🛌 1 Inflatable Airbed 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included

4.67 out of 5 average rating, 311 reviews

Sentral Premium 2BR Apt South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

4.84 out of 5 average rating, 118 reviews

McCormick 2B/2Ba w opt parking for up to 6 guests

• 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 HDTVs in ALL ROOMS(Netflix and Roku) • Fully equipped & stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Flat in Ukrainian Village

4.9 out of 5 average rating, 527 reviews

iKlektik House Chicago / Robin

CLOSE TO THE UNITED CENTER! Bright, Sunny and Stylish one bedroom, full kitchen, balcony overlooking the backyard in West Town WITH FREE STREET PARKING. Close to Wicker Park, Ukrainian Village West Town and Bucktown. The space is amazing...just read the reviews! Very cozy! There is FREE street parking. WiFi Speed has been upgraded to 1200mps!! NEW mini-split system that is very quiet heating and cooling. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM

4.82 out of 5 average rating, 129 reviews

Apartment in South Loop

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of the Park & Lake ✅ Central Location ✅ Parking garage attached to building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Rooftop Deck ✅ 1 block from Red, Orange, Green "L" subway ✅ Close proximity to Park, Soldier Field, Museums

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Popular amenities for rentals with a firepit in South Loop, Chicago

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a firepit

4.96 out of 5 average rating, 122 reviews

Home in Bridgeport

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

LuciaRating, 5 stars2 weeks ago

We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.

4.9 out of 5 average rating, 367 reviews

Home in Lake View

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

4.97 out of 5 average rating, 152 reviews

Home in Wilmette

Unique porcelain-enamel paneled "Lustron" home

MichelleRating, 5 stars2 weeks ago

We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=

4.94 out of 5 average rating, 148 reviews

Home in Avondale

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars1 week ago

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

4.98 out of 5 average rating, 114 reviews

Home in Lincoln Square

Entire first floor in Lincoln Square!

MeganRating, 5 stars1 week ago

We loved Nora’s apartment! It was perfect for two adults and an infant. The pack n play plus high chair were huge helps to have on-site. The free laundry in building laundry was also fantastic. The apartment is charming, clean and close proximity to the park and main strip of restaurants and shops in Lincoln Square. We would definitely stay at Nora’s again.

4.86 out of 5 average rating, 137 reviews

Home in Chicago

Boho Chic Coach House 30Min to downtown W/ Parking

LinaRating, 5 stars1 week ago

I loved the little cottage. Quiet neighborhood, felt safe. Restaurants were walkable. Reached out to Marilyn for a breakfast recommendation and checked out bacon and jam, amazing. House was easy to find. Clear instructions. Felt at home.

4.92 out of 5 average rating, 137 reviews

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

AshleyRating, 5 stars1 week ago

A great spot!! A friend and I were in town for a concert and this place was perfect! The patio was really cool and Tom has the cutest dog!!

4.95 out of 5 average rating, 151 reviews

Home in Logan Square

The Grand Kimball Lodge, Logan Square, Sleeps 14

AndrewRating, 5 stars3 weeks ago

Our hosts were excellent - communicative, welcoming, friendly. We were greeted by Bob who was very laid back and accommodating. He offered good recommendations and amenities during our stay. The space is perfect for large groups and certainly impresses with its charm and personality. The neighborhood is walkable to the Blue Line and many bars/restaurants. Overall 10/10 a perfect stay and would absolutely book again in the future.

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Apartment rentals with a firepit

4.82 out of 5 average rating, 45 reviews

Flat in Humboldt Park

Sunny garden apartment in West Logan Square

NatRating, 5 stars4 days ago

Cozy and great place! The neighborhood is quite safe and very close to 606. The rooms are spacious and clean.

4.98 out of 5 average rating, 103 reviews

Flat in Humboldt Park

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

BriantRating, 5 stars1 week ago

We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.

Flat in McKinley Park

4.8 out of 5 average rating, 5 reviews

Cozy apt close to Loop & MDW 1 Free Parking Space

Gia HuyRating, 5 stars2 weeks ago

Amazing place and wonderful host. The host was extremely accommodating and responsive. Would totally recommend

4.98 out of 5 average rating, 51 reviews

Flat in Uptown

Private studio near Wrigley

SteveRating, 5 stars1 week ago

It’s been an amazing stay here in Chicago! The Airbnb is really Cozy and spacious. Nicholas and Aaron took care of every little detail to make our stay very pleasant. It’s really easy to get to downtown Chicago with the strategic location. It’s close to Wrigley Field and nearby restaurants and bars. It a safe area in a quiet neighborhood that is very walkable. I would recommend this place to anyone visiting Chicago!

4.92 out of 5 average rating, 51 reviews

Flat in Albany Park

Montrose Gardens

AndrewRating, 5 stars1 week ago

Great location, walkable from Metra & CTA stations. Cozy space. Exactly what I needed

4.9 out of 5 average rating, 527 reviews

Flat in Uptown

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

NikkiRating, 5 stars4 days ago

This was my first time booking with Airbnb and all I can say is that it could not have been a better experience! Aaron was so nice and beyond helpful. The apartment was the perfect size for my husband and I. It is in a good location, we were able to get to anything we needed or wanted with just a short walk. Not only that but the building itself was so cool, the lobby is beautiful and the amenities were spectacular. We ventured to the rooftop many times because of how nice and peaceful it was. We attended a concert at the Aragon Ballroom and it’s the first time we’ve not stressed about how to make the trip there and back. It was maybe a 3-5 minute walk at most! Overall it was beyond what I was expecting. If available, anytime we will be in the area this will be our first choice!!

4.93 out of 5 average rating, 126 reviews

Flat in Logan Square

Logan Square Garden Sanctuary

PricillaRating, 5 stars6 months ago

Tess’s place was exactly as described. Very clean and there were lots of little extra amenities that were appreciated. Seemed they thought of everything! Extra toothbrushes and disposable razors, Q-tips, cotton balls, snacks, water and more! Our only issue was spotty internet which might have been due to provider outages. Wasn’t too much of an issue for us as we were out exploring the city most of the day.