We’re big fans of the Windy City of Chicago, and why wouldn’t we be? The city boasts everything from an unparalleled bar and restaurant roster to a vibrant art scene. And, of course, there’s the amazing deep-dish pizza, which we couldn’t get enough of. However, what interested us the most in Chicago was the interesting skyline and architecture. So, we thought, why not start with our Airbnb? Many examples of the city’s historic cityscape actually lie outside downtown, and it’s an eclectic collection of neoclassical-meets-gothic-meets-modernist. The best Airbnbs in Chicago range from restored prairie-style Frank Lloyd Wright homes to industrial lofts with soaring ceilings.
Superstar architects don’t get more famous than Frank Lloyd Wright, and the Windy City is full of his wondrous creations, ones we could actually rent! His most famous creation is the meticulously restored 1915-built Emic Bach home, which is often called “stacked cubes.” It boasts common Prairie forms, color schemes, and materials blended with modern comforts, which made our stay as historic and memorable as comfortable.
That’s not all that Chicago is known for. We’re talking, of course, about the iconic deep-dish pizza, which we discovered multiple versions of on this Downtown Pizza Guided Walking Tour. And trust us when we say that we needed all the walking after gorging on all the deep-dish pizzas! It’s no wonder that Chicago was voted the “Best Big City in the U.S.” for the fifth straight year, which is evident from the video below. So, what are you waiting for? Check out this guide to the Windy City’s Airbnbs.
Modernist Pilsen Loft
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Chicago is famed for its loft rentals, and this Modernist Pilsen Loft is among the best of the lot. This bright, light-filled, two-bedroom loft was perfect for us as have a hankering for modern decor. That, mixed with vintage furniture, really made this space an Instagrammable darling. Our mornings were reserved for enjoying tea and coffee in the yellow sunroom before catching up with some work in the sun-soaked office nook. The living space with a cushy couch and huge TV was perfect for spending time together after a long day of exploring the city.
The chefs among us really loved the huge, modern kitchen, as it had everything we needed to prepare a lavish meal. The main bedroom, with its retro-pink bathroom and bathtub, and the loft bedroom were both cozy to boot and ensured a good night’s rest. Finally, the southside Pilsen location puts us smack dab in the heart of the Chicago Arts District, which is all about museums, mosaics, and murals.
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Enchanted Garden Treehouse
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Best for couples. You’d think vacation rentals in the Windy City would be all brick structures, right? Imagine our delight when we found a perfectly gorgeous treehouse to stay in, and that too just 30 minutes from downtown! Welcome to the Enchanted Garden Treehouse, a dreamy vacation rental hidden away in the suburb of Schaumburg.
We completely forgot about the real world once we entered this magical one-bedroom cedar treehouse, which offers views of a koi pond and a stunning waterfall right beside it. The outdoors is absolutely stunning, complete with a bird and flower-filled garden with a cedar hot tub. It was perfect for enjoying a long soak to ease our sore muscles after walking all around Chicago.
The inside of the treehouse was equally blissful, with a cozy king bed and a TV right next to it. A ladder led to a single bed in the loft, where we’d cuddle up and lie watching the stars. Completing the picture of perfection was the kitchenette, where we’d cook romantic meals and enjoy the perfect getaway in the Windy City.
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Retro Andersonville Condo
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Trust Chicago to have the most beautiful and vintage vacation rentals we’ve ever seen in our lives! We’re talking, of course, about this lovely two-bedroom Retro Andersonville Condo, which screams vintage from a mile away. It’s only fitting that it sits in eccentric Andersonville, a northside Chicago neighborhood with Swedish roots. When we came to the private ground-floor apartment, we found a lovely, well-tended garden welcoming us. A quirky red door welcomed us within a neat little living space with colorful artwork, turquoise-blue accents, and the yellowest walls we’d ever seen. The rest of the condo is equally minimal and modern, especially the beautifully restored kitchen, where we could easily cook meals thanks to the updated appliances. Two comfy bedrooms with the plushest queen beds in the world and a modern bathroom complete the place.
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Wicker Park Spring Factory Tea Studio
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We’d heard a lot about Chicago’s industrial loft rentals, and we were dying to live in one of them. And we were fortunate enough to stumble upon the utterly gorgeous Wicker Park Spring Factory Tea Studio.
We felt veritably boho-chic as we stepped into this stunning rental, a restored one-bedroom loft in a converted tea factory. The interiors are all about lots of artwork, wooden accents, and soft earth hues.
The professional-grade kitchen was the main draw of rental for the chefs amongst us, but that’s not all we loved about this space. Since the owner is crazy about everything Japanese, we found everything from a Japanese soaking tub and a bamboo wall to a collection of rare teas. We especially loved the decor that pays homage to the building’s esteemed history as a tea factory. Think a window-panel wall, exposed pipes and brick, and Industrial light fixtures. Wrapping up the space is the equally lovely bedroom, which is great for couples looking to cozy up during their Chicago getaway.
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Victorian-era NOLA-style Mansion
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Best for luxury enthusiasts. Southern charm is present in spades at this four-bedroom Victorian-era NOLA-style Mansion, which is one of the best Airbnbs in Chicago. We were transported to what felt like the setting for a Southern Gothic novel when we entered this Victorian-era home. Styled with a NOLA-esque flair, this space is all about opulent decor and parlor rooms. Think oil paintings, a fleur-de-lis sunroom, high-backed velvet chairs, and bric-a-brac all over. What’s more, they’re spread out across three floors, which also feature five fireplaces and multiple parlors!
That said, it’s the 4,000 sq feet of space that had us charmed right off the bat. There was not just a pool table parlor, but also a light-filled atrium which was the perfect spot to cozy up with a book. The roof deck was an absolute delight to use as we were in Chicago during the summer. We even had a backyard with a grill to spend time in, especially when we wanted to enjoy barbequed meals alfresco. Four queen/double beds in the bedrooms and luxe bathrooms with a mix of modern and vintage fixtures had us retiring comfortably every night. A full kitchen, a laundry room, and a separate “mother-in-law” basement unit (with a separate entrance for the host) complete this place.
If you’re looking for an indulgent place to stay, then look no further than this Airbnb, which has everything you need – and then some!
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Room in Andersonville Home
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Best for budget travelers. If you’re looking for a room rather than an entire apartment or space, then a private room in this quaint Andersonville Home is perfect for you. The bedroom boasts a very comfy queen bed that is perfect for resting our weary heads after a long day. It was very spacious, complete with a cable TV, free Wi-Fi, and a large window bringing in plenty of light. The shared bathroom with heated tile floors lay just outside for utmost comfort. That said, the shared and outdoor spaces are fantastic here, and the hosts are even better. There were days we’d relax in the yard or on the huge deck overlooking the pond and stream all day, sipping coffee and cocktails. The hosts even invited us to join them for coffee in the mornings or cocktails in the evenings. How cool is that!
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Rock N Roll River North Apartment
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Most unique Airbnb. Are you a fan of rock n’ roll like us? Then you will love this two-bedroom Rock N’ Roll River North Apartment. The neighborhood was once home to a flagship Rock N’ Roll McDonald’s, which not only had themed decor but an entire exhibit on the history of the genre. The theme might have exited the McD’s, but it still lives on in this apartment. It’s loaded with rock n’ roll kitsch such as old records, Elvis cutouts, and guitars. We almost felt like we were walking into our own personal museum of memorabilia!
The rest of the flat is equally impressive and comfortable. Both bedrooms have queen beds; one is more romantic with a four-poster bed, while the other keeps up with the rock n’ roll vibe of the place. Our days began in the full kitchen, where we’d prepare coffee and breakfast. At the end of the day, we’d wind down with a glass of wine and kick back on the cushy living room sofa to a soundtrack of vinyl.
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Frank Lloyd Wright-designed Emil Bach House
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We were perhaps most excited about staying at the Emil Bach House, famously designed by Frank Lloyd Wright. This three-bedroom Chicago landmark even sits on the U.S. National Register of Historic Places and is called the “stacked house” because of its boxy appearance. We had an exceptionally enjoyable stay in this architectural treasure of a house, as it’s been painstakingly updated with mod-cons. It felt as if Lloyd Wright was guiding us through the entrance and the main floor, which was designed that way. Since we were a group of six adults, we’d love to get together in the living room, complete with a fireplace. We’d cook meals together in the full, modern kitchen and enjoy them together at the dining table.
Three bedrooms with pillow-top beds and two bathrooms aside, this place even had a study with its own balcony for relaxing and working remotely. Thanks to the washer-dryer in the basement, the Emil Bach House was perfect for our extended Windy City stay. That said, we loved the outdoor areas here, which include not only landscaped gardens but also a Japanese tea house!
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Shangri-La Artist Loft Duplex
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When one says Shangri-La, we immediately imagine a mythical, mystical, permanently happy Himalayan utopia. That’s what the three-bedroom Shangri-La Artist Loft Duplex is – only this one sits in the heart of Chicago in the River West neighborhood. Housed in a 1904-built former picture frame factory, this renovated home retains original elements like hardwood floors and exposed brick walls. However, it’s gotten major updates in the form of a full kitchen with modern appliances and even a new washer-dryer. But that’s not all.
This loft is primed for entertainment and even has a private screening room with a home theater and an Xfinity cable package! That means we had access to Amazon Prime, Netflix, etc., and spent every night watching our favorite movies. Even the bathrooms have gotten major updates, and we loved indulging ourselves in the huge Jacuzzi and the Grohe body spray showers. Heck, there’s even a pool table with a comfy chair swing right next to it to spend hours having fun right in the house. Oh, and did we mention that Alexa lives on the kitchen counter? Yes! Three bedrooms with the plushest king mattresses in the world complete the place.
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Edgewater Glen Home
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It’s hard not to fall in love with this beautiful sun-drenched, historic Edgewater Glen Home. Since it’s a historical space, the one-bedroom apartment is actually a suite as a part of a larger home. The highlight of the open-plan living room is the picturesque windows that look onto the leafy street. The kitchen is right next to it, with just a lovely teal-colored breakfast bar with seating separating them. It would be where we’d have coffee and breakfast every morning. The eclectic furnishings perfectly complement the bright wood floors, the stark white walls, and the stunning repointed brick masonry wall. We had a whale of a time clicking pictures for our Instagram feed for sure! The bedroom with the walk-in closet aside, there’s a lovely front porch with chairs where we could sip coffee and watch the world go by.
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Cortland, Logan Square
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Best location. The centrally located Cortland in Logan Square is hands-down one of the best Airbnbs in Chicago. We couldn’t have asked for a better location for our Windy City stay. For one, this four-bedroom home sits right in the heart of the leafy Logan Square. And we couldn’t go wrong staying here, what with its proximity to most of the top things to do in Chicago. What’s more, the house itself is amazing, with an immersive design and a smart home system that’s second to none. With six king and queen beds, this home had enough room for our large party of 12 people.
The expansive living-cum-dining space was the ideal spot to rest our feet after a day of sightseeing and architecture peeping. We had the full chef’s kitchen at our disposal, and meal-making times were as fun as eating times. Thanks to the washer-dryer, free Wi-Fi, and free parking, we were able to enjoy our extended stay thoroughly and without a hitch. Finally, we loved relaxing and unwinding in the back patio and garden, which had lots of alfresco seating.
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Our Verdict!
Write a summary paragraph to tell the readers why these hotels are the best based on our judgment. Follow with a list of these more specific categories:
- Best for luxury enthusiasts: Victorian-Era NOLA-Style Mansion
- Best for budget travelers: Room In Andersonville Home
- Most unique Airbnb: Rock N Roll River North Apartment
- Best for couples: Enchanted Garden Treehouse
- Best location: Cortland, Logan Square
Where to Stay in Chicago?
Chicago has some of the most richly diverse neighborhoods in the world. We start with Downtown Chicago, or The Loop, as it’s famously called. It’s a great place to stay, especially for first-timers, as it’s home to some of its biggest and best attractions and architectural landmarks. Next, we’re going to talk about Wicker Park, which is famous for its entertainment avenues, bustling nightlife, and dining venues.
Of course, there’s no talking about the best Chicago neighborhoods without talking about the Magnificent Mile. This prime Chicago shopping district lies just across the Chicago River and is luxurious to the last mile. We also love the prospects offered by Lincoln Park, which is a verdant neighborhood and is perfect for checking out the local life.
What is the best area to stay when visiting Chicago?
The best location for first-time visitors to stay in Chicago is Downtown, a.k.a. the Loop, which lies right at the center of the city.
Is Chicago a walkable city?
Chicago, especially downtown, is easy to navigate via walking. What’s more, many other parts of the city boast pedestrian-friendly designs and sidewalks, too.
What is the best way to travel in Chicago?
Trains and buses of the Chicago Transit Authority (CTA) are an excellent, cost-effective, and fast way to get around the city.
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