These 5 Chicago Airbnbs Will Have You Flying the W

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You haven’t seen anything until you’ve seen Chicago.

Planning a trip to The Windy City? Located right on Lake Michigan, Chicago is one of the most beautiful cities in the country. Before you snap your photos at Skydeck or The Bean, get comfortable in one of these Airbnbs.

Whether you’re taking a business trip or visiting for pure entertainment, you’ll want to take advantage of the beautiful amenities these Airbnbs have to offer. Indulge in the city life or relax in the suburbs — the choice is yours. The only requirement is that you enjoy your stay!

1. This Cozy Chicago Airbnb Feels Like Home

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What it features:

This two bedroom home in Chicago can comfortably sleep up to five guests. It features a private entrance and carport, allowing for a stress-free stay.

A breakfast bar with leather stools and leafy house plants make this space comfortable and welcoming. Unique, industrial-style metal finishing boasts a calm city vibe. Even equipped with a guide book of the city, guests will never run out of things to do!

Why it’s a great place to stay:

“Beautiful, clean home in a convenient location. Check in and check out was super easy and they were quick to respond and even let us check in a little early. Thoughtful touches throughout the place and a great list of recommendations on the fridge! Would highly recommend and stay again.” - Guest Review

How much it costs:

$92 per night

How to book it:

Rent this Chicago home on Airbnb here.

2. This Chicago Apartment Offers Unbeatable Views of the City

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What it features:

Conveniently located in the South Loop, this two bedroom apartment can sleep up to six guests. It’s just a short distance from Grant Park and a number of other fine restaurants, bars, and shopping options.

This Airbnb’s elevated design brings the feel of the big city to the comfort of the indoors. The modern, high-end kitchen provides a great space for cooking and enjoying meals. Plus, massive windows offer spectacular views of the Chicago skyline. Why it’s a great place to stay:

“I booked this place for a girl’s birthday trip, and we absolutely LOVED it! The pictures were accurate. The views were breathtaking. The beds were super comfortable. They provided a lot of kitchen supplies. It’s not a bad walk to downtown (10-20 minutes, super quick if you use the blue line which is a block away). They had extra pillows and blankets. Everything was cleaned. I HIGHLY recommend it!! I will definitely be booking with Kasa for future Chicago trips!” - Guest Review

How much it costs:

$186 per night

How to book it:

Rent this Chicago apartment on Airbnb here.

3. This Chicago Studio Includes A Private Hot Tub

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What it features:

This cozy studio provides the perfect level of intimacy while remaining spacious. It’s ideal for just one or two guests, so arrive solo or bring your partner along. The private outdoor hot tub sits in the leafy, fenced-in yard.

High ceilings, exposed silver ducting, and eclectic decorations create a one-of-a-kind space for guests to indulge in. The kitchen is functional and well supplied. Not to mention, this Airbnb is situated in a great location.

Why it’s a great place to stay:

“Brad was extremely helpful and easy to communicate with. The hot tub was a great addition to our stay and that was the comfiest bed we’ve ever slept on! My boyfriend and I had a great time and would definitely stay here again in the future.” - Guest Review

How much it costs:

$146 per night

How to book it:

Rent this Chicago apartment on Airbnb here.

4. This Light-Filled Loft in Chicago Boasts Modern Excellence

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What it features:

This Airbnb is artsy, cozy, and full of immense character. The sunshine and open layout of the apartment make it feel spacious yet inviting. It features glossy black and white hardwood floors, translucent walls, and a bright yellow balcony room.

Located in Pilsen, the surrounding neighborhood is cute, quiet, and has excellent dining choices. It’s also not a far ride to Chicago’s downtown.

Why it’s a great place to stay:

“Daniel and Tes’ loft was spectacular! Very unique in style but up to date on amenities. Pilsen is a good neighborhood and it was very close to the city and both my job. Beyond the amazing space, Daniel and Tes were very friendly and engaging and made sure I was comfortable and even recommended plenty of places for me to explore!” - Guest Review

How much it costs:

$105 per night

How to book it:

Rent this Chicago loft on Airbnb here.

5. This Stunning Chicago Home Was Designed By Frank Lloyd Wright

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What it features:

Stay in a true architectural treasure at this beautiful Chicago home! Designed by Frank Lloyd Wright himself, the space has been carefully updated to preserve history while affording modern conveniences.

With three bedrooms, up to six guests can comfortably stay here. Featuring multiple balconies, patios, and even a Japanese Tea Room, guests might find it difficult to leave this wonderful Airbnb. When it’s time to venture out, the home is only a block away from Lake Michigan.

Why it’s a great place to stay:

“Wow! Amazing to stay in a beautifully restored Frank Lloyd Wright house with all the luxurious modern amenities. Perfect for my husband and I with 4 teens visiting Northwestern and University of Chicago.” - Guest Review

How much it costs:

$486 per night

How to book it:

Rent this Chicago home on Airbnb here.