Chicago, Illinois is one of the biggest and brightest gems in the Midwest and a true great amongst American cities. It has renowned architecture and over forty museums, not to mention nearly 7000 restaurants that serve up some famous food like Chicago deep-dish pizza and Chicago hot-dogs. If you’re headed to Chicago, you’re in for a real swell time.

However, trip planning just wouldn’t be complete without figuring out where to stay. While hotels cost more than a pretty penny and hostels aren’t really a thing yet in Chicago, we think that Airbnbs in Chicago are the way to go! Check out our list of rentals in Chicago below to figure out which of our top 15 Airbnbs are right for you.

We’ve sorted them out by travel group size, style, vibes, and budget for your convenience. Ready to find the perfect Chi-Town Airbnb for you? Let’s get to it!

Quick Answer: These are the Top 5 Airbnbs in Chicago

City View Apt with Pool and Gym

City View Apt with Pool & Gym

  • > $
  • > 2 guests
  • > Access to Pool & Gym
  • > Private Sauna
Sunny Room in Central Apt

Sunny Room in Central Apt

  • > $
  • > 2 guests
  • > Memory Foam Mattress
  • > Free Parking Space Provided
Artsy Apartment With Funky Vibes

Artsy Apartment With Funky Vibes

  • > $$
  • > 2 guests
  • > Private free parking
  • > Unique Artwork & Atmosphere
Stylish Apt w Thoughtful Touches

Stylish Apt. w/ Thoughtful Touches

  • > $$
  • > 8 Guests
  • > High Chair & Crib
  • > Modern Space w/ Custom Comforts
Zen Loft in Downtown

Zen Loft in Downtown

  • > $$$$
  • > 10 Guests
  • > Gourmet Kitchen
  • > Seven TVs

Looking for other types of accommodation? Check out our guide to Where to Stay in Chicago!

Why Stay in an Airbnb?

  • Local Experience: Having a local as a host means you can find out all the best places to visit and things to do that are off the beaten tourist track. That doesn’t just go for Chicago, but for all travel destinations in the Illinois.
  • Unique properties: Airbnb has every kind of property you could think of. There’s even a ‘unique stays’ search function, where you can find your dream property on the site.
  • Privacy: Another great filter – choose an entire place to ensure you won’t be disturbed during your trip. 
  • Safety: It might seem a little weird staying in someone’s house; however, both hosts and guests are vetted by Airbnb reviews to ensure the safety of both. Chicago is overall safe, and the Airbnb booking security just adds a little extra to it.
  • Airbnb Experiences: Choosing Airbnb isn’t just about where to stay – it’s about enjoying the area like a local with curated tours, too!
Airbnb Chicago
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The 15 Top Airbnbs in Chicago

Whether you’re visiting Chicago over the weekend or end up staying long term, there is always the right Airbnb waiting for you. To make the search a bit easier for you, we’ve listed the absolute top Airbnbs in Chicago down below.

Overall Best Value Airbnb in Chicago | City View Apt with Pool & Gym

City View Apt with Pool and Gym
  • $
  • Private Sauna
  • 2 Guests
  • Access to Pool & Gym

This incredible studio loft is an unbelievable find in Chicago. Coming in at an astonishingly low rate, this Chicago Airbnb is not one to pass up on. With a swimming pool, basketball court, gym, and private sauna the amenities of this complex have been out of this world at this price point. Just a few steps off your front door is the historic State Street and the Magnificent Mile.

You’ll be very close to the Navy Pier, as well as other tourist hotspots. There is even a lovely balcony that is perfect to enjoy taking in a breath of fresh air.

Best Budget Airbnb in Chicago | A Budget Traveler’s Dream Room

A Budget Travelers Dream Room
  • $
  • Luggage Drop-Off
  • 2 Guests
  • Billiards Room

This one private bedroom Airbnb in Chicago is a wonderful homestay option for those looking to save some dough so they can spend it instead on the deep-dish dough! Yes, we have a joke or two up our sleeves…if you thought that was cheesy (you know, cheese/pizza) wait til you see what else we have in store.

Anyways, this Chicago Airbnb offers guests a stay in a historic Victorian-era home. The room has a king size bed, as well as a sofa bed for those traveling in a group size larger than two. Also, guests are invited to use the full-size kitchen as well as the outdoor and indoor living room areas. There is also even a billiards room that guests can enjoy and play a game of pool! It’s definitely one of the best Airbnbs to stay in Chicago on a budget!

Budget Tip: Dorms in Chicago start from $20USD per bed. They’re the cheapest accommodation in the city. Search for hostels in the area!

Perfect Short-Term Rental for Digital Nomads | Heavenly Room w/ Breakfast

Heavenly Room w Breakfast
  • $
  • Breakfast Included
  • 2 Guests
  • Washer & Dryer In-Unit

This private room short-term rental in a Chicago homestay is a dream come true for the digital nomads out there. With a comfy queen-sized bed and a room filled with plenty of sunlight, you’re staying in digital nomad heaven. There is also a mini-fridge, desk, chair, ironing board, and TV inside your room itself.

Guests are welcome to use the balcony and the seating area, as well as the in-unit washer and dryer. With just a fifteen minute walk to downtown, you’re close to everything you could need. There is actually even a restaurant directly below this apartment, so you won’t have to go far for a bite to eat! This is the best Airbnb in Chicago for digital nomads for sure!

Perfect Airbnb for Solo Travelers |  Cozy Studio Apt. Close to Downtown

Cozy Studio Apt Close to Downtown
  • $
  • Vibrant Neighborhood
  • 2 Guests
  • Free Parking

This one bedroom and one bathroom short-term rental in Chicago is perfect for the solo travelers out there. It’s a small studio, with hardwood floors, that is best described as sweet and simple. Also, there is a kitchenette to use that has all the basics, including coffee for those java fiends out there.

If you’re looking for somewhere to stay on a budget, as a solo traveler, with no frills or fickleness, this is the Chicago Airbnb for you! Located in Pilsen West side, this is a spot full of arts and culture and delicious food, not too far from Downtown at all. Just a 15 minute ride on public transportation is all you need!

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Best Airbnb in Chicago for Nightlife | Modern Room in the Heart of Loop

Modern Room in the Heart of Loop
  • $
  • Use Apartment to Fullest Extent
  • 2 Guests
  • Free Coffee & Tea

Chicago is home to hundreds of incredible bars and pubs, quite a few of which are now city landmarks. If you’re heading to Downtown, you’ll be surrounded by incredible nightlife from the Tiki bar of Three Dots and a Dash, to the London House Rooftop Bar, to the glitzy Z Bar. It’s hard to pick just one bar to visit, so go ahead and visit a few!

This one bedroom and one private bathroom room rental in a Chicago apartment is the perfect place to stay to be close to all the nightlife. The room itself is spacious and has high ceilings. Also, guests are lol allowed to use the apartment to the fullest, and enjoy using the kitchen, dining room, living room, and laundry facilities. This is just a two bedroom and two bathroom apartment, so you only have to share the apartment with just the hosts themselves.

Best Short Term Rental for Couples | Artsy Apartment With Funky Vibes

Artsy Apartment With Funky Vibes
  • $$
  • Unique Artwork & Atmosphere
  • 2 Guests
  • Private free parking

This one bedroom and one bathroom Chicago apartment is perfect for your Chicago getaway. It is in a great location of Chicago’s Wicker Park/Bucktown community. It’s just one block from the subway and is conveniently located near great eateries and shops. There is a comfortable queen-sized bed, as well as a kitchenette with a refrigerator and microwave.

This beautiful home makes for a memorable stay for couples visiting the Windy City. With free private parking to boot, this is the best Chicago Airbnb for all you love-birds out there!

Best Homestay in Chicago | Sunny Room in Central Apt

Sunny Room in Central Apt
  • $
  • Free Parking Space Provided
  • 2 Guests
  • Memory Foam Mattress

Located in the heart of downtown, with easy self-check-in and with free luggage drop-off, this is an incredible Chicago homestay. The hosts allow early check-in, as early as 11:00 am, and also provide a free parking spot for your car. The location is truly incredible! Just a five-minute walk to the University of Illinois Chicago, and a five-minute walk to public transportation— it’s also just a quick five-minute ride on the metro to Downtown!

Since it’s not in the heart of Downtown, it’s quiet enough that you won’t hear any shenanigans going on outside at night. Enjoy a peaceful night’s sleep in this beautifully designed Chicago Airbnb!

Runner-Up Homestay in Chicago | Picturesque Master Suite w/ Hot Tub

Picturesque Master Suite w Hot Tub
  • $
  • Hot Tub
  • 2 Guests
  • Private Bathroom w/ bathtub

This private room rental is a wonderful Chicago homestay. This short-term rental is for a large master suite room that has plenty of space to move around and breathe. Located just outside of the center of Chicago, it’s just a ten-minute ride metro ride to downtown or to other popular tourist spots from Millenium Park to the Willis Tower.

Additionally, the private bathroom is divine. Complete with a bathtub and a shower, you can enjoy a warm bubble bath after a long day exploring Chicago. This host also allows last minute reservations, canceling within 24 hours for a free refund, and no security deposit. So if you’re a little unsure about your travel specifics, this Chicago Airbnb is the one for you!  What’s better having an Airbnb with a hot tub? (Well, an Airbnb with 2 hot-tubs and a helipad. But we can’t fine one).

Amazing Luxury Airbnb in Chicago | Stunning Downtown Artist Loft

Stunning Downtown Artist Loft
  • $$$
  • Brick and Timber Styled Loft
  • 2 Guests
  • Washer & Dryer

This one bedroom and one bathroom apartment in the West Loop of Downtown Chicago is a dream. It’s got a rustic vibe going on, with exposed brick walls and moody lighting, yet modern with its furnishings and tasteful touches. It’s a 900 square foot traditional brick and timber loft that has all the amenities you could need. The washer and dryer make your stay in this Chicago Airbnb even easier. The minibar and Keurig machine are also great additions!

This big, open, stylish loft is the answer to all your Chicago travel problems.

Over-the-Top Luxury Airbnb | Zen Loft in Downtown

Zen Loft in Downtown
  • $$$$
  • Seven TVs
  • 10 Guests
  • Gourmet Kitchen

This four bedroom and two bathroom loft in Old Town Chicago is drool-worthy. It’s 3,500 square feet of zen heaven. The artwork and furnishings, a mix of industrial and magazine-worthy enormous artwork make this Chicago Airbnb a haven of Instagram-worthy shots. Additionally, there are four queen beds and one full bed, as well as air mattresses and baby cribs being available. There are a total of seven TVs, including two 75 inch tv’s strewn throughout this enormous apartment.

Best Airbnb in Chicago for Families | Stylish Apt. w/ Thoughtful Touches

Stylish Apt w Thoughtful Touches
  • $$
  • Modern Space w/ Custom Comforts
  • 8 Guests
  • High Chair & Crib

This three bedroom and one bathroom Chicago apartment comes with a total of four beds. If you and your big family are heading off to Chicago, this is the Airbnb for you! There is a free parking space in the garage, as well as a fully equipped kitchen and even a high chair for the kids. Also, there is high-speed WiFi 250-350 MB/sec so the kids won’t be complaining about the internet struggling to load the My Little Pony show on youtube.

Situated in the South Loop of Chicago, you’ll be less than 3km away from Grant Park, the Art Institute of Chicago, and the Field Museum of Natural History. This is one of the best Airbnbs in Chicago in terms of furnishings and facilities as it’s filled with lots of thoughtful touches that will make you and your family feel right at home.

Best Airbnb in Chicago for a Group of Friends | Aloha Dreamy Paradise

Aloha Dreamy Paradise
  • $$$
  • Giant Neon Palm Tree Sign
  • 10 Guests
  • Skylights & High Ceilings

This four bedroom and two bathroom Chicago Airbnb has a total of five beds. It’s located in the heart of Wicker Park— where there are endless things to do and see! The decor is super fun, with an enormous neon palm tree sign and giant pink shark adorning the walls. This entire apartment seems to come right out of a Hollister magazine, with bright furnishings and whacky knick-knacks, from seashells to tiki statues.

The kitchen is stocked up with everything you need, that really goes beyond the basics including a blender and a waffle maker!

Best Airbnb in Downtown Chicago | Spacious Apt By Millennium Park

Spacious Apt By Millennium Park
  • $$$
  • Ideal Location Facing Michigan Ave
  • 2 Guests
  • Gym & Pool Access

Spacious and minimalist, this one bedroom and one bathroom Chicago apartment is right by Millennium Park, facing Michigan Ave. It’s less than a 10-minute walk to incredible Chicago tourist hot spots, from the Art Institute to Grant Park. If you’re traveling without a car, and don’t want to deal with metro cards and long walks, this is the Chicago Airbnb for you!

Moreover, this Chicago apartment is quite well-equipped to make your stay extra comfortable, from complimentary breakfast items, to plenty of clean towels, to a TV with Netflix already hooked up! In the building itself, you’ll get to use the indoor pool and the 24-hour gym. There is also a doorman on-site 24-hours a day for an added safety feature.

Another Great Apartment in Downtown Chicago | Calm Studio in Downtown Core

Calm Studio in Downtown Core
  • $$
  • 2-Min To Millenium Park
  • 2 Guests
  • Great Views from Apt

This one bedroom and one bathroom studio apartment is perfectly located Chicago Airbnb right in the heart of Downtown. Seriously, it couldn’t be more Downtown than this! Truly unbeatable location. Sightseeing all happens within a two-minute walk! There is also Pizzano’s just around the corner that serves up some famous Chicago deep-dish pizza! This Chicago apartment is just what you’re looking for. Of course, it includes all the basics from fuzzy, fully towels to a fully-equipped kitchen.

You’ll be sitting pretty in this Chicago Airbnb.

Top Value Airbnb in Lincoln Park | Artsy Apt with Great Value

Artsy Apt with Great Value
  • $$
  • HDTV & High-Speed WiFi
  • 2 Guests
  • Quality Air-Con

This one bedroom and one bathroom studio apartment in Lincoln Park is packed with value. In terms of location, there is fantastic food and vibrant nightlife just outside this Chicago Airbnb’s doorstep. The Orange Cafe is on the same block, for a fabulous brunch or Trader Joe’s is up the block if you want to snag some goodies to cook your own meals in the fully equipped kitchen. It’s a very comfortable space, with a cozy bed filled with little artsy touches from pillows to paintings.

An extra air mattress can also be provided should an extra guest be tagging along!

FAQ about Airbnbs in Chicago

Here’s what people usually ask us when they look for vacation homes in Chicago.

Final Thoughts on Chicago Airbnbs

Chicago is quite the fun city to visit! With plenty of skyscrapers and fantastic museums to visit, there is very nearly too much to do in Chicago for just one trip! Hopefully, our list of the top 15 best Airbnbs in Chicago helped you check one very important item of your trip-list: accommodation planning! Let us know in the comments below which Chicago Airbnb was a dream come true for you.

If you’re heading to Chicago, you might want to look at some travel insurance. We’d like taking a peek at  World Nomads and requesting a lighting-fast-no-strings-attached quote. Go get ‘em tigers!

And don’t forget to take out Travel Insurance for your trip! I have been using World Nomads for some time now and made a few claims over the years. They’re easy to use, professional and relatively affordable. They may also let you buy or extend a policy once you’ve started your trip and are already abroad which is super handy.

If there’s one insurance company I trust, it’s World Nomads. To find out why I use World Nomads, check out my World Nomads Insurance review.

Getting an estimate from World Nomads is simple – just click the button or image below, fill out the necessary info, and you’re on your way!

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