Sunday, January 29, 2023

Best Places To Stay In Chicago Airbnb

Best Airbnb For Quirky Stays In Chicago

Best places to visit in the world, best beautiful places in the world #bestplaces

Sunny Character-Filled Apartment in Trendy Ukrainian Village

Youll score a stay right by the happening quarter of Ukrainian Village at this Airbnb. Youll also score a truly unique pad. It flaunts a prestigious Plus rating for its stylish interiors, which bring together elements of exposed brick and 1950s Pop Art. Theres a single bedroom, a fitted kitchen, and tonnes of artistic touches to keep the eyes busy.

Why Stay At A Chicago Airbnb

Luis Boucault/Shutterstock

There are many appealing attractions in the city of Chicago. Going there for a family vacation or even just a weekend getaway will allow you to see a fantastic culture and take in incredible restaurants and entertainment options.

When staying in Chicago, you will see that hotels rooms can be limited in space. Due to the citys size, the square footage of available properties is limited. Therefore, you will find that rooms are smaller to accommodate more rooms and visitors.

One way to work around this is to stay at an Airbnb instead of a hotel. With more space, furnished bedrooms, and kitchen access, you will often find more space for the price when going the route of an Airbnb.

With the vast amount of Airbnbs available today, it can be hard to narrow down your search to find the best ones. To help you plan, we have rounded up a list of the 15 best Airbnbs in Chicago.

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Things To See And Do In Wicker Park

  • Visit the Flat Iron Arts Building, an all artist studio building.
  • Browse the stacks for your new favourite book at Quimbys Bookstore, an independent shop.
  • Listen to legendary artists and great live music at Subterranean.
  • Line up and get ready for the most amazing tacos at Big Star.
  • Try incredible diner-style dishes at Doves Luncheonette.
  • Start your day with a satisfying and indulgent breakfast at Mindys HotChocolate.
  • Sink your teeth into a tasty burger at Presidio.
  • Head up to Bloomingdale Trail also known as the 606 and enjoy amazing views of the city.
  • Sip extraordinary cocktails on the rooftop at Whiskey Business & Fry Bar.

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Which Chicago Airbnb Is Best

While we would love to point to just one option and declare it the best choice for your Chicago getaway, every visitor has their vision for the perfect accommodation. Therefore, there is no one size fits all selection that meets the needs and wants of everyone.

The Airbnbs listed above have many positive reviews and offer high-quality amenities to their guests. When youre planning your next visit to Chicago, be sure to reference this comprehensive list to find the best Airbnb for you and your group!

Fairfield Flat Airy Vintage Rehab

15 Best Airbnbs in Chicago, IL (2021 Edition)

The Fairfield Flat is a remodeled first-floor apartment, sitting close to the famed California Pink Line Station, Lagunitas Brewery and Tap Room, Douglas Park, and Petes Fresh Market. Just a short train ride away, there is Pilsen and West Loop.

Just like the Roosevelt Suite-Garden Studio, the apartment lies on the Little Village. Your stay here will give you an experience of mixed Mexican and Black American culture. They are the dominant inhabitants here and expect hospitality and mutual respect. However, take note that space does not allow filming or other productions.

Also, the apartment features a living room, a fully equipped kitchen, and a dining room. The master bedroom boasts of a sizable closet and vanity. Theres also a guest bedroom with under-bed storage, and both spaces contain window unit air conditioners.

Guests here can have access to private areas of the apartment, including the large patio. They can even make use of the barbecue grill and smokers but on a first-come, first-serve basis. The host also offers bicycles with helmets.

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Best Homestay In Chicago

  • $
  • 2 Guests
  • Memory Foam Mattress

Located in the heart of downtown with easy self-check-in and free luggage drop-off, this is an incredible Chicago Airbnb homestay. The hosts allow early check-in, as early as 11:00 am. They 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. Its also just a quick ride on the metro to Downtown!

Since its not in the heart of Downtown, its quiet enough that you wont hear any shenanigans going on outside at night. Enjoy a peaceful nights sleep in this beautifully designed Chicago Airbnb that will quickly feel like home!

Dont Forget Your Chicago Travel Insurance

Hey, I know, paying for insurance is no fun. But neither is paying medical bills.

Trust me, you dont want to know what that experience is like in the USA. Just get insured.

Its good to get lost sometimes, but its also good not to get too lost. There are people that want you home in one piece.

Theres one travel insurance provider The Broke Backpacker trusts for all his wildest shenanigans World Nomads!

And then let the shenanigans begin.

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Bespoke Wicker Park Suite No 2 By Zencity

The Bespoke Wicker Park Suite No. 2 offers one of the most attractive options you can get based on Airbnb Chicagos set of reviews. It lies appropriately at the border of Wicker Park and the Ukrainian Village atop a 3-story walk-up. It can accommodate up to five guests with its two bedrooms, two beds, and one bathroom. All these are fully-equipped with the essentials to give you a comfy stay.

Best Budget Airbnb In Chicago

Best places to visit in the world, best beautiful places in the world #bestplaces
  • $
  • Walking distance to public transit
  • 2 Guests
  • Billiards Room

This private bedroom Airbnb in Chicago is a wonderful budget option for those looking to save some dough so they can instead spend it on some deep-dish dough! Because as youll soon learn, thats the real highlight of any Chicago itinerary.

This Chicago Airbnb offers guests a stay in a historic Victorian-era home thats only 3 minutes walking distance from public transit. 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 you can play a game of pool in! With plenty of space, fast Wifi, and an unbeatable price, its definitely one of the best Airbnbs to stay in Chicago on a backpackers budget!

  • 10 Guests
  • Gourmet Kitchen

This four-bedroom and two-bathroom loft in Old Town Chicago is drool-worthy. Its 3,500 square feet of zen heaven. The artwork and furnishings, a mix of industrial and magazine-worthy pieces, make this Chicago Airbnb a haven for Instagram-worthy shots.

Additionally, there are four queen beds and one full bed, as well as air mattresses and baby cribs available. There are a total of seven TVs, including two 75 inch TVs strewn throughout this enormous apartment. While you can imagine that the price sure aint cheap, it becomes relatively affordable if you have a large group!

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Modern Chicago Loft With A Complimentary Garage Spot

Those looking for the best Airbnb rentals in Chicago will definitely want to take a moment with this apartment. Situated in the neighborhood of Avondale, this Airbnb Plus provides you with a central location that has shops and restaurants nearby, as well as easy access to downtown.

The first thing to jump out at you with this Chicago loft will be its clear sense of style. Inside theres plenty of exposed brick and classy, modern decor that makes the space immediately inviting. Since this is a studio apartment, couples and solo travelers will find themselves best suited to staying here. Theres plenty of comfort offered here thanks to the queen bed with memory foam mattress, while the studio makes the most of its space with a nice lounge area and even a little study space.

Guests wanting to prepare their own meals will be pleased with the apartments full kitchen, complete with a gas oven and stove, dishwasher, and coffee maker. Other modern amenities include Wi-Fi, heating, and air-conditioning, and the option for self check-in. Finally, guests also have access to a little balcony and free on-site parking.

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What To Expect From Airbnbs In Chicago

There are a ton of Airbnbs in Chicago, and they come in a seriously wide variety. From trendy, modern lofts downtown to listings that more closely resemble houses in the suburbs, theres an Airbnb in the Windy City for every budget and preference.

Centrally located Airbnb Chicago rentals tend to be more expensive, but thats the trade-off for being near the citys top attractions. If youre down to choose a place thats a bit farther away, you can save yourself some cash and instead use it on eating and exploring expenses.

With hundreds if not thousands of options to choose from, you should be able to quickly score a cool accommodation for your trip! Heres a bit more of a breakdown of what Airbnbs you can expect to find while planning your trip to Chicago:

Things To See And Do In Lincoln Park

Top 25 Airbnbs In Downtown Chicago, Illinois
  • See all your favourite animals from lions, tigers and bears to birds, reptiles and fish at the Lincoln Park Zoo.
  • Wander throughout the expansive and stunning Lincoln Park.
  • Explore the botanical gardens near the shores of Lake Michigan at the Lincoln Park Conservatory.
  • Dive deep into the citys rich and storied history at the Chicago History Museum.
  • Rest and relax on North Avenue Beach.
  • Tease your taste buds by digging into to a stack of pancakes at Batter & Berries.
  • Eat an incredible pot roast at Nookies.
  • Try Chicagos best pizza pot pies at Chicago Pizza & Oven Grinder.
  • Sample unique flavours and sweet treats at Mollys Cupcakes.

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Gold Coast And Lincoln Park

The Gold Coast is an exclusive neighborhood in the northern parts of Chicago right next to Lake Michigan.

With its beautiful combination of modern highrise buildings and traditional stand-alone homes, The Gold Coast contributes a great deal to the citys skyline.

This affluent part of town is for the most part very calm and quiet and would, therefore, be perfect if you are looking to escape the hustle and noise of livelier Chicago districts.

A little further north you will find the Lincoln Park community.

Here, you will find the world-famous zoo with the same name, numerous galleries and a thriving food scene.

Best Neighborhoods To Airbnb In Chicago

Chicago is divided into 77 community areas with 178 neighborhoods. With so many options, it can be difficult to pick the best place to Airbnb in Chicago. To help with your decision, I provide insight on the most popular Airbnb in Chicago locations.

Downtown neighborhoods are a great option for both first time visitors and business travelers. Many tourist attractions are located near River North and Streeterville. Business travelers should also consider the Loop and South Loop neighborhoods if they want to be close to most office buildings.

Neighborhoods north of downtown are also some of the most popular Airbnb in Chicago locations as they are close to the lake and home to the Lincoln Park and Wrigley Field. A few specific neighborhoods to consider are Lakeview, Lincoln Park and Old Town. Wrigleyville is also great for baseball fans.

Personally, I am a big fan of the west side of Chicago. Some of the best areas to Airbnb in Chicago include Wicker Park, Logan Square and West Loop. Throughout these neighborhoods, youll discover great restaurants, local taverns and trendy shops.

Each neighborhood has something unique to offer. I recommend taking several trips and staying in a different neighborhood on each visit to Chicago!

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Find The Best Chicago Str / Airbnb Property

Alex curates a list of properties that have a high chance of allowing Airbnb. From his experience, the average property has less than a 1% chance. His list has a ~50% chance. Beyond identifying the best properties for STR / Airbnb, Alex helps his clients de-risk and ensure their property will be approved by the city of Chicago before closing.

Buyers can find a Chicago property for Airbnb but it takes a partnership between the broker and the buyer to succeed. Active buyer involvement and the willingness to move on quickly if a deal falls apart during the de-risking process is required.

Contact Alex Cross if youre looking for guidance on how to buy a Chicago STR condo for Airbnb. Moreover, should you need help setting up, managing or optimizing your short term vacation rental check out his site Vacation Rental Advisory.

And by the way, if youre considering buying a house instead of a condo for Airbnb, check out our tips for buying a house for Airbnb in Chicago.

About the Author:Licensed since 2005, Chuck Gullett is the managing broker at Best Chicago Properties in Chicagos West Loop. He is consistently recognized as a Top Producer and has a true passion for real estate. Chuck is also the owner of ThreeSixtyChicago specializing in real estate photography. An earlier version of this article appeared in the January 2020 edition of Real Producers Magazine. The original version of this article was published by Best Chicago Properties, LLC on November 15, 2018.

Chicago Observation Deck: 2

Best places to visit in the world, best beautiful places in the world #bestplaces

âSkip the ticket line twice to enjoy the best panoramic views or a spectacular sunset over Chicago â 94 stories above the Windy City. Enjoy breathtaking 360 degree views across 4 states and Lake Michigan. See the sights in a different light.â

Price: From $28.50 USD

Review: âAmazing experience. I loved being able to go twice and experience the views. Completely different views. Enjoyed the night view betterâ Maureen â United States

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Planning A Trip To Chicago Or The Usa

Youâve made an excellent choice! Chicago is an exciting place to visit, and thereâs so much to see, do, and experience. While I plan on adding a lot of content about Chicago to my blog in the future, I do have a ton of U.S travel content to check out for other destinations you may want to visit across America.

Now that youâve hopefully found the best Airbnb Chicago has for you, I recommend the blogs below, which include city guides, Airbnb, and music festival lists plus so much more!

Stylish Studio In The Heart Of Logan Square

This beautiful studio apartment is located right in the heart of the hip Logan Square neighborhood. With a bedroom nook and tons of extra sleeping space, this cozy Chicago Airbnb can sleep up to six guests. Its perfect for couples wanting a romantic getaway or small families looking to be right in the heart of the action!

The thoughtful owners have put love and care into every detail of this Airbnb. Youll find cool amenities all around the studio including a record player with a selection of vinyl, original artwork, and tons of plants. The hardwood floors, picture-perfect vaulted ceilings, and modern décor all work to give this vacation home its unique character.

You can have a movie night in the homey living room, catch up on some reading on the comfy futon, or get some work done at the designated workspace. The kitchen is surprisingly spacious and has everything you need to cook at home. Enjoy your meals and morning coffee in the sun-drenched breakfast nook.

If you feel like going out, all of Logan Squares best restaurants, shops, and cafes are a short stroll away. Be sure to brunch at local favorite Lula Café and grab a beer at the ultra-popular Revolution Brewing!

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Best Airbnb In Chicago For Nightlife

  • $
  • 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 youre heading to Downtown, youll be surrounded by incredible nightlife from the Tiki bar of Three Dotsand a Dash, to the London House Rooftop Bar, to the glitzy Z Bar. Its hard to pick just one bar to visit, so go ahead and visit a few!

This one-bedroom with 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.

Which Neighborhood For Airbnb Rental

Amazing Airbnb Chicago homes you can rent

Hi all,

My husband and I are visiting Chicago for a long weekend in July. We have visited many times and have mostly stayed within a block or so of Michigan Ave. But last time we rented an AirBnB and stayed in a neighborhood near Wrigley. We loved feeling like “locals” and spent time in that neighborhood exploring shops and restaurants.

My question for this summer is – what are some good neighborhoods for me to target as I look for a place to stay? Requirements are:

Very near the El

Very walkable neighborhood with fun restaurants and shops to explore

We are both 40, and won’t have our kids with us. We aren’t that interested in live music, so aren’t necessarily looking for that.

Gold Coast

Before you pull the trigger on a rental, please post the cross streets of the rental that you’re considering. Many Airbnb landlords aren’t quite truthful in terms of location and safety issues.

Lincoln Square, and Andersonville.

A couple notes

– The Field Museum is not particularly near an el stop. Depending where you start, a bus is often a better idea.

– Most of the North side neighborhoods are not super convenient from O’Hare airport on the el because you have to go downtown and then back out again. To go to somewhere like Lincoln Park, for example, a train plus bus from O’hare is probably better.

Here’s a link to the prohibited buildings listing:

Edited: 4 years ago

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