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 link further 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! If you’re looking for a luxury Airbnb in Chicago or something more budget-friendly, I’ve got you covered.

Best Airbnbs in Chicago

I’ve been booking Airbnbs for the last 5 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 if it’s 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 locations 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 just 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 around. 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 located in Wicker Park, close to tons of 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 certainly an impressive 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 normally 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 to book a stay that’ll let you take in the beautiful view. So, I did the work for you. I dug around for some of the best-rated Airbnbs in town that offer just that and more, some even have private rooftops!

Lux Sky Home near Navy Pier and the Mag Mile

This apartment seems to have a view from every single room! There are 2 bedrooms, 2 bathrooms, a private balcony, and a cool 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 has to offer 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 if you can swing it (or split it) then it’s worth the splurge. It has 5 bedrooms, 4 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. Plus, 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 one 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 great views, 2 beds, 2 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 is run by a company, but with these views, I’ll have to reconsider. 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 2 bedrooms, 2 baths, and offers some of the coolest views of the city. You won’t want to leave. | BOOK HERE



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  • 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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