The Best Bars Close the Chicago L: The Blue Line

So you've arrived in Chicago and booked an Airbnb. You ask the host where and what the nearest public transportation is to check out some of the great nightlife around Chicago. They tell you that a short few blocks away is the "blue" train line.


Have no fear! If you’re looking for a good night out on the town, and  a way to get around at the same time, you're in luck.  Welcome to our 4 part series of “The Best Bars Around the Chicago L”.

We’re going to go over the 5 best bars around the various stops on the Pink, Red, Blue and Brown L lines. This piece will be about the Blue Line.

Let's hop on this train and get going!

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Revolution Brewing

Neighborhood: Avondale

L Stop: Belmont

If you say you are from Chicago, then you have had a Revolution! Revolution beer and Revolution Brewing that is. Revolution Brewing is Chicago's favorite craft brewery. Since its opening in 2010, Revolution has become such an iconic Chicago brand, that it has virtually revived neighborhoods such as Logan Square and Avondale. The main brewery is in the Avondale neighborhood.

This is the best beer in Chicago in our opinion. The brewery has a HUGE taproom where the brewing process is in full view with wooden barrels in every corner, overseen by a glorious American flag. I love taprooms but this is my favorite one. Though huge in space, the taproom has a neighborhood feel, comfortable whether you're with friends or alone. But even when you are there alone, it doesn't feel so. Like America's favorite fictional bar, this is where everybody knows your name.

The brewery also has brewery tours almost daily.  On Saturday, they have it at 4, 5, and 6 PM. The brewery tour is very popular and is first come first serve and no appointments. You will see what a real micro brew operation is like. Unlike an Anheuser Busch tour, it's much more homey and cozy and the tour feels as if your drunk Uncle Johnny is giving you a good story to tell. Plus at the end of the tour, you get a nice cold can of Anti-Hero beer!

So, come check out why Revolution beer is the best craft beer in Chicago. Check out one of the greatest looking taprooms you will ever see. And check out the newest Chicago hot spot, where artists, professionals, and craft beer enthusiasts all happily converge in one place called Revolution Brewing! 

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Logan Bar and Grill

Neighborhood: Logan Square

L Stop: California

A new kid on the block seems to be appearing every week in Logan Square. Home of hipsters, artists and long time locals for years now is catering to the newest yuppies, young parents and wannabes (first the skyscrapers, what's next Baby Gap?). But if there is one thing constant, it's good old Logan Bar and Grill. You see, long before the newest, trendiest bars and restaurants opened in LS, LBG was already there. Serving the locals and the newest community members with happy service and good selection of beer, liquor and food.  

Yes the food! Such good bar food! That's usually my stop when I want good bar food with good beer because LBG has both. Options are plentiful from your typical nachos, wings and sandwiches to burgers. But what's not typical is how delicious they are. Hand crafted burgers with tastes for every palette. Your stomach won't feel empty as the dishes are sizable though your mouth might savor for more because it's so tasty.

Another reason to stop here besides, the food, drinks selection and being right next to the California Blue line, is how chill and relax the atmosphere is. Sure, you can go to a more crowded bar. A more dive-y bar. Even a more pretentious bar (yes they are creeping in Logan Square now, argh!), but Logan Bar and Grill has never changed - in a good way. Their service is impeccable from the moment you walk in, to the moment you leave the table. They seem to know how to hire the right people. Maybe it's because they want to keep the old Logan Square we knew and loved before it started changing. I'll stop myself there before I hurt anyone's feelings about their neighborhood. Bottom line, make Logan Bar and Grill your first stop in Logan Square before going to any other bars and you'll see that at the minimum, you'll have made at least one right choice that night.


Flat Iron

Neighborhood: Wicker Park

L Stop: Damen

Speaking of neighborhoods that are losing their way...cough, cough, our next stop is Wicker Park. In its heyday, Wicker Park was the Logan Square of Chicago. Every weekend and sometimes it seems, every weekday, people were always out and about. The energy level was vivacious and contagious. Besides plenty of original watering holes, places like Double Door would attract the coolest and best local acts that only people in the know have heard about. Unfortunately Double Door is closed and many other bars that made Wicker Park have been replaced by venues that are not beholden to the original contract of keeping it authentic. But the good news is there are still some places that exist for that purpose. And Flat Iron is one of them.

Flat Iron, for some novice to Wicker Park, may seem to him or her as not their cup of tea. Large, dark, grungy, dive-y, full of interesting wall art. But look past your mental box of what a bar you like should be, to what it feels like instead. And Flat Iron feels just right.

Come to Flat Iron because you miss the old Wicker Park. You know the one where you can be yourself. The one where beer is still affordable. The one where the guy sitting next to you may be from a different background but still can shoot the bull with you. The one where you can be alone and not feel alone. The one where playing pool or bar games isn't a hassle to start. That's Flat Iron. Now, isn't this nice and the way more bars in Wicker Park should be? 


Easy Bar

Neighborhood: Wicker Park/Ukrainian Village

L Stop: Division

Continuing on our quest to find another cool yet unpretentious bar, let’s stop and take a look on Division Street. There’s so much going on on Division Street, so let us make it easy for you: Easy Bar.

Easy Bar on Division street is easy alright. Walk right in, and the music doesn't stop. Walk right in and easily play a game of pool with a stranger. Walk right in, and the bartender or even the GM will say hello and serve you a beer quickly, yet have time to chat with you until the next customer beckons. Walk right in and sit at the bar, watch a game or go all the way to the back to their comfortable, yet history laden lounges. Yes it is dark and has an unassuming decor but that's part of what makes Easy Bar easy. No pretension, no fluff, no BS. But it's more romantic than meets the eye. The lit candles and the smooth music generate the mood for you and your significant other or the interesting guy or girl that you have an eye for. Easy Bar can get crowded late Friday or Saturday night but no matter what time you go, you'll feel at ease and at home.


Richard's Bar

Neighborhood: River West

L Stop: Grand

Alright, we have mentioned many good bars in our "Best Bars Around the Chicago L" list including some old school type bars. Holiday Club in the Red Line is a good example. But for a truly old school experience you have to visit Richard's Bar.

Located in the Milwaukee/Grand/Halsted six corners area, Richard's Bar is usually not the first bar that comes rolling off someone's tongue. And that’s because the neighborhood is not the newest or trendiest one to go to (though that will probably change quickly). That award goes to the likes of River North or Logan Square. And that’s just fine cause Richard's Bar is not built or catered to mass appeal. Besides, the look and feel of this bar hasn't changed for 50 years (even the bartender seems like he came of the 1940’s!). For one, the bar sells cigarettes and even have patrons smoking. Now, I know this will turn off many people, as most of us don't smoke anymore, but if you can handle some second hand smoke, the experience at Richard's is one to take home with. Some people come dressed like the "old movie" days with their hats and long blazer coats. Listen or play the jukebox that's always on and beloved by everyone in the room. People watch and let time slow down for you. That's Richard's and if you like all that, then step off the Grand station and immerse yourself in a different era.

Five great spots on the Blue line for you to check out. There are plenty of more bars along this route but since we cannot make them all, check out these five first! 

How To Handle Taxes with Your Airbnb and Short Term Rental

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With short term rental regulations changing day-day, it’s important to keep up and adapt with the regulatory landscape. A simple change, like ski-town, Breckenridge’s requirement of a responsible agent, can add another expense to your P&L.

Are you tracking your income and expenses for your short-term rental on Airbnb? Do you have an accountant to help with with your taxes? Have you considered the tax ramifications of your Airbnb, especially for your Airbnb in Chicago?
The good news is that there are tools and resources that can help you. And if you REALLY don't want to deal with them, we can help ;) Here are tax insights for your Airbnb:

Go Pro? The Right Questions to Ask

Whether you choose to prepare your taxes yourself or have a professional do them for you, it’s important to get the full scope of the tax implications so you know your true return, ie yield. We recommend walking through your taxes with professional help.

If you choose to do your taxes yourself, there are some resources that provide educational tools to understand the tax process. Ernst and Young and Airbnb havean in-depth guide here. This a must for most every Airbnb host. You'll learn how to cover everything from deducting maintenance costs to reporting rental income.

Here is a local guide for Illinois and Chicago taxes. The most relevant questions to ask yourself include:

  • How much of your Airbnb income must you report?

  • Which tax deductions do you qualify for?

  • Which forms should you file?

  • How can you stay compliant with estimated taxes and penalties?

How To Handle Taxes with Your Airbnb and Short Term Rental

Tax deductions are great because they help you pay fewer taxes. An Airbnb tax deduction is incurred in Chicago when you incur an expense in order to generate more income. For an Airbnb host, this may include:

  • Mortgage or monthly lease payments

  • Sheets, linens and other soft goods in your rental unit

  • Wi-fi

  • Cleaning fees you pay to a service provider

  • Netflix/entertainment service costs

The important thing is to track your expenses. In order to claim these deductions keep all receipts and proofs of purchase in order to reduce your risk of tax penalties.

The 14-day Exception: Room-sharing

If you rent out one room in your house, the 14-day rule applies in the same way as if you rent out your property. If guests stay for 14-days or less, you don’t have to report the income , but you cannot take any deductions either

Track+Keep records of rental periods

Airbnb and short-term rental platforms are nice because they help you track and keep records. If you rent out your place for two weeks or less, keep track of rental days and days you use the residence yourself.

If you rent for longer than the 14-day exception period, detail the dates precisely so you can properly divide out personal and business expenses, like mortgage interest.

Airbnb Occupancy Tax in Chicago

In Illinois and Chicago, the municipalities impose occupancy taxes on short-term rentals. These vary widely from one jurisdiction to the next, from the name of the tax—hotel tax in some states, transient lodging tax in others—to the rates and rules. Here are the tax rules for Chicago.

Sometimes, the host is required to collect the occupancy tax directly from renters and submit the money to the tax authority. However, in certain cities and states Airbnb collects and submits the taxes. Airbnb imposes and remits these taxes in Chicago.

Self-Employment Taxes for Your Airbnb

Depending on how you structure your Airbnb business in Chicago, you may have to pay self-employment taxes, as well as income taxes. Self-employment taxes cover Social Security and Medicare contributions for income you make when you are in business for yourself.

When you Airbnb your home, make bookings and provide amenities like coffee or breakfast, the IRS treats you as being self-employed in the vacation rental business.

Prepare, prepare, prepare

Track, prepare, and use a professional is our best advice. Airbnb is still a new tool so always be prepared to receive a letter from the IRS. Don’t worry, just keep all of your documentation at hand.

Airbnb's Economic Impact in Chicago - 2017


Airbnb, the short-term rental platform, continued to grow in the Chicago market in 2017. And it isn't welcome news for the city's hotel industry.

For travelers who like the Airbnb experience, it is a positive sign to connect people to local culture, bring business to little-known neighborhoods, and provide unique travel experiences.

Airbnb's Chicago 2017 economic impact study states that Airbnb hosts' income totalled $77 million last year, up from the $67 million earned by hosts in 2016.

Airbnb hosts welcomed 500,000 guests in 2017, a significant jump from the 390,000 guests reported in 2016. Total Airbnb guest spending in 2017 was estimated to be $270 million, with average spending per day by Airbnb guests pegged at an estimated $171.

Airbnb operations in Chicago generated a total economic impact of $345 million in 2017, up from $331 million a year ago.

In their report, Airbnb takes pains to note that the proliferation of homesharing in Chicago has particularly benefited the city's South Side, where growth in guest arrivals in 2017 was up 70 percent compared to the previous year.  Much of the South Side is more economically depressed than other parts of the city, and Airbnb looks to be serving as something of an economic stimulant.

Perhaps to ward off any more salvos aimed at Airbnb by Chicago's hotel industry, the home-sharing service included some upbeat data about Chicago's hotel business in its economic report.

Chicago's hotel industry has been particularly paranoid about the Airbnb threat since the service started gaining traction in Chicago. Per Airbnb, Chicago hotel occupancy increased to 75.19 percent in 2017, up from 72.1 percent in 2011. And Chicago annual hotel revenue has increased 39 percent since 2011, from $1.64 billion to $2.28 billion.

To make hotel companies feel a little less paranoid, Airbnb pointed out today that 94 percent of its Chicago listings are outside of the Loop, the epicenter of the city's hotel business.

Founded in 2008, Airbnb is now a presence in 65,001 cities in 191 countries around the world. If you're curious why it is called "Air" bnb, send us a message.