11 Amazing Airbnbs in Chicago (Including the Best Views)

Whether you’re visiting Chicago or just a local in need of a break, here are 11 of the best Airbnbs to fully enjoy your trip.

With this being my hometown, I understand the overwhelm of choices when it comes to Airbnbs in a big city. I also know all the best neighborhoods to stay in and explore, and I link additional Chicago guides below.

This Airbnb list is full of everything from an art gallery condo to the best views in the city and even a castle-like stay! I’ve got you covered if you’re looking for a luxury Airbnb in Chicago or something more budget-friendly.

Best Airbnbs in Chicago

I’ve been booking Airbnbs for the last five years and am very careful about where I stay. I’ll share more on how I choose a place so you can feel more confident about this list.

The host needs to be a superhost because, from my experience, 9/10 times, they go above and beyond. Typically I only book Airbnbs where I can reserve the “entire place” since we like our privacy. I’ll maybe stray from that if it’s super unique or a bed & breakfast type place.

I search for Airbnbs with a rating of 4.90 and above. I will only go lower if the place and location look incredible, and I can’t find a concerning review. Also, I always make sure the areas of the Airbnbs are optimal for my travels, and I’m not wasting time commuting during a trip.

During this 2020 pandemic, I look for “enhanced cleaning.” This means that the host is committed to Airbnb’s 5-step enhanced cleaning process.

Note: All photos courtesy of Airbnb and belong to the individual Airbnb owners.

Modernist, Creative, Light-Filled Loft in Pilsen

I love the sunshine-yellow balcony room! This space seems to breathe life into any season you can experience in Chicago (especially our gray winters). This loft is located in the Pilsen neighborhood.

Pilsen is an art-filled area that offers lots of cool murals and some of the best restaurants. So you’ll not only be inspired by the creative space you’re staying in but also the neighborhood you can easily explore. | BOOK HERE

Wicker Park Spring Factory Conversion

The coolest factory-turned loft is located in Wicker Park, close to many restaurants, bars, and cafes. This artsy space provides enhanced cleaning, a king-sized bed, and a Japanese soaking tub! Plus, you’ll be steps away from just about anything you need. | BOOK HERE

Hip & Historic Coach House in Humboldt Park

What used to be a machine shop is now an airy, sunny studio perfect for 2. The studio is located in Humboldt Park, close to Wicker, with lots of great local spots and easy access to public transportation. I love that it has both a soaking tub and a rain shower because who doesn’t want options? | BOOK HERE

Handcrafted Art Gallery Condo in River West

This gorgeous art gallery condo is roomy (for up to 8), has city views, a private balcony, and some pretty cool mentions. It’s been featured in Architectural Digest and Condé Nast Traveler. It’s undoubtedly a unique place located in Chicago’s River West neighborhood. | BOOK HERE

Room 21 at Castle-Like Oak Park Mansion

Okay, this castle-like Airbnb looks so cool and unique! I know you’re not booking the “entire place” as I usually prefer, but this seems to be more like a B&B without breakfast. They rent out several rooms (each with a private bath), and the one I linked is the most reviewed private room in the house.

This historic 1905 Revival Tudor seems so spacious that I’m sure you’ll have plenty of privacy. It’s located in Oak Park, one of Chicago’s prettiest suburbs. It’s two blocks from Frank Lloyd Wright’s home and two blocks from Hemingway’s Birthplace Museum. You’ll be surrounded by history. | BOOK HERE

Chicago Airbnbs with a View

Chicago is filled with impressive architecture that is famous around the world. One of the best things you can do when exploring this city is book a stay that’ll let you take in the beautiful view. I dug around for some of the best-rated Airbnbs in town that offer just that and more; some even have private rooftops! So, I did the work for you.

Lux Sky Home near Navy Pier and the Mag Mile

This apartment seems to have a view from every single room! There are two bedrooms, two bathrooms, a private balcony, and a fabulous rooftop you can enjoy — all showing off different views of the city. It’s located in downtown Chicago, so you’ll be in the heart of many things the city offers, including some of the most popular tourist attractions. | BOOK HERE

Old Town Penthouse with Private Rooftop

This stunning 4,000 sq ft penthouse is perfect if you have a larger family. It’s located in Old Town, one of my favorite Chicago areas. This luxury Airbnb is the priciest one on this list, but it’s worth the splurge if you can swing it (or split it). It has five bedrooms, four bathrooms, a jacuzzi tub, steam shower, fireplace, and your private roof deck with panoramic views of the city. | BOOK HERE

Apartment in The Loop steps to Millenium Park

This downtown apartment faces one of my favorite views. Spot the Chicago corn cobs (Marina City) in the background! If you’re looking for a simple, affordable, well-rated place with incredible river and city views, this is your place. You’ll be steps away from Millenium Park and the Willis Tower. | BOOK HERE

Penthouse with Views from Private Rooftop

This line alone sold it for me, “Soak up sweeping skyline views and sparkling city lights from the luxurious rooftop terrace at this light-filled penthouse.” You won’t be near the river, but you’ll experience Wicker Park, one of the coolest neighborhoods in Chicago. Milwaukee Avenue alone is lined up with bars, restaurants, and shopping. And you’ll be staying in a lovely apartment with your very own rooftop, what more can you need? | BOOK HERE

Modern Gold Coast Apartment Lake Views

This apartment is located in the Gold Coast area, another of my favorite Chicago neighborhoods. You’ll have plenty to do right outside your door! In my opinion, the Gold Coast is one of the most picturesque areas in the city. This Airbnb has excellent views, two beds, two baths, and access to the rooftop pool when in season. | BOOK HERE

Sonder Apartment at Essex on the Park

I’m usually wary of booking an Airbnb that a company runs, but I’ll have to reconsider with these views. Also, with the great reviews and extra covid precautions, I think this place may be a winner. It’s located in the South Loop, right across from Grant Park. It has two bedrooms, two baths and offers some of the most incredible views of the city. You won’t want to leave. | BOOK HERE



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  • Reply cow squishmellow August 16, 2022 at 5:32 am

    I visited Chicago in 2019 and I cherished it! I desire a good way to visit once more! I truly love a majority of these places that you shared! They are so first-rate that I don’t know which one to choose

  • Reply Kay December 12, 2020 at 8:15 pm

    I WANT TO VISIT CHICAGO FOR THE VIEWS ALONE!! i think I lean more towards the airbnbs that have a light modern feel, but that’s just me! Haha

    • Reply Lily December 13, 2020 at 9:39 pm

      I love those Chicago views!😍

  • Reply lisa December 12, 2020 at 2:42 pm

    Wow, these airbnbs are amazing! I love the Mansion and the Lux Skyscraper airbnb – both are so unique and gorgeous! <3

    • Reply Lily December 13, 2020 at 9:39 pm

      Right? I want to move in to some of these!

  • Reply Ophelie December 12, 2020 at 2:39 pm

    I visited Chicago in 2019 and I loved it! I hope to be able to visit again! I absolutely love all these places that you shared! They are so amazing that I don’t know which one to choose!

    • Reply Lily December 13, 2020 at 9:38 pm

      Thanks for reading! I hope you make it back too 🙂 it’s such a great city.

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