The Best Bars Around the Chicago L: The Brown 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 "brown" 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 Brown Line.

Let's hop on this train and get going!


The Red Lion

Neighborhood: Lincoln Square

L Stop: Rockwell

The Red Lion is a cozy neighborhood pub hidden in quaint Lincoln Square. The English styled pub prepares and serves fares grown locally with what it calls "Heritage Recipes", family recipes it says passed down from England for over 100 years. It features a large selection of twenty five classic and unique single malts such as Balvenie, Oban, Auchentoshan, Caol Ila, Bowmore and others. They also feature small batch Bourbons and Ryes. Their beer list includes over thirty five local, craft and imported beer, from the UK of course. For an intimate pub, that's an impressive list!

Another reason to stop by The Red Lion is, if you haven't guessed, the amount of Englishness it has. From a painting of the elegant Queen Victoria and a victorious English sea battle to the staff wearing a bearskin hat (you know the ones you see red English guards wearing?), it's a perfect place for an Anglophile to visit. Even if you're not, it's definitely a charming place to have a beer before you head to the next bar on the Brown line.

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Neighborhood: Lincoln Square

L Stop: Western

Since we're on the subject of great European style bars, let's move on to one of the other great countries in Europe, Germany. And being Lincoln Square with its traditional large German population, Huettenbar would have to be on the top of the list.

Huettenbar is a classic German pub. It has an Old World decor to it like its triangular roof, wooden front doors, sloped wood paneled ceiling and a floor of multicolored ceramic tile in earthy tones. The bar name is inspired by Alpine slopes which "Huettenbar" is loosely translated as "mountain hut/bar" in German. From the moment you enter the bar to sitting down, you'll feel like you stepped into an Alpine village pub.

Huettenbar doesn't serve food but it does serve plenty of German beers. It has 10 beers on tap like Kutschen Alt and Spaten and a nice selection of German liqueurs, such as Jagermeister, Westfalen Jager, Kabanes, and more fruity flavors like Edel-Kirsch, Echte-Kroatzbeere, Crazy Ananas , and Barenjager. 

Now that you have found an authentic German bar in Chicago, we're ready for our next stop for more great drinks! 


Schubas Tavern

Neighborhood: Lakeview

L Stop: Southport

Now that you have been to two cool bars that remind you of Europe, it's time to step into a bar that has been a staple of the northside and known for its great musical acts.

This bar is Schubas, a Lakeview establishment that goes wayyy back. Schubas was originally built around the turn of the 1900's as one of the Schlitz Brewery tap houses (they have Schlitz in bottles today). You can tell immediately the history of this place walking in. And though it sits on Southport street, it has the feel of a small neighborhood corner bar. Entering inside, the green-painted front room opens up to a 30-foot Brunswick mahogany bar. Above are traditional looking ceiling fans with tin ceiling above. You'll see the bar room with old bar goodies like a jukebox, photo booth, old TV's and even a mounted elk head.

And if you have all day, try their 70+ different types of hard alcohol, including a selection of bourbons, and several beers on draft and in bottles.

But the bar is as we said known most for its live music shows. On a weekend evening, you'll hear music even before you enter the doors. This Lakeview spot has everything a music fan wants - a small inviting room, excellent sound and an atmosphere that music fans can appreciate. Local bands come to belt their music, anywhere from rock, country, funk, indie, jazz to even folk. Usually you can come to the music room without a ticket but it's a good idea to call ahead.

So come to Schubas in the day for a low key affair or come at night to hear some great local music.


Local Option

Neighborhood: Lincoln Park

L Stop: Fullerton

Looking to drink at an intimate bar with great craft beer without all the hype or pretentions in Lincoln Park? Perfect, stop at Local Option! 

Local Option is nestled in a quiet Lincoln Park neighborhood, not far from DePaul. Which this is why it may surprised you that the crowd at Local Option is not college-heavy but instead gravitate toward a more mature crowd from later 20's to 50's. The more mature, but beer sophisticated crowd, like Local Options array of delectable craft beers. Names like Mourning Wood, Outlawger, Exorcist, Sky burial and so on. Interesting names aside, the beers are crafted strong and flavorful, ranging in alcohol content of six to as high as fourteen percent. It's definitely a craft enthusiast's dream.

Food is another intriguing aspect about Local Option. They range from NOLA style fare to Mexican food. The wide selection makes you want to try it all but definitley go for their jambalaya and tacos as well as their po'boys. They are good, good, good!

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Neighborhood: Old Town

L Stop: Sedgwick

As our train rolls around the bend to Old Town, we get off on the Sedgwick stop. Here we step foot into Old Town, a neighborhood west of Gold Coast, north of River North and east of Wicker Park. Money seems not to be a problem with its expensive condos all around but don't be intimidated, there are many good bars here. One of our favorite bars in this neighborhood is Corcoran's. 

Walk into Corcoran's and get ready to explore.The first bar is small and narrow, with not much room to stand but as you keep walking past tables you'll find a cool beer garden. Sit with your friends and talk about life or just people watch as others walk by. Or keep on going and you'll step into a "coach house" of sorts known as "Thade's Room." This room is quite unique. Always happening and full of fun people, it's a place you'll always remember, even if you had too much too drink! The beer garden and Thade's Room is what makes Corcoran's a great place for a cold Sunday drink or just a really fun Friday night out.

Five great spots on the Brown 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! 

Chicago's Growing Airbnb Culture and Investment Market

Want to explore the little-known neighborhoods of Chicago? Own a home in one of Chicago's hidden-gem neighborhoods? There is a growing trend of short-term renters and travelers in Chicago. According to Airbnb, in 2016 there were 300,000 travelers in 2016. 500,000 in 2017. Wow. That is growth.

It is creating a new culture along with it, too. The lesser known neighborhoods, and their businesses, now benefit in unexpected ways.

The Overview: Airbnb In Chicago

Airbnb gives property owners with extra space to rent a platform to connect with travelers. Through the Airbnb platform, owners and investors in Chicago can list their property with images, amenities, and details for their ideal guests.

Chicago travelers look through the listings, and when a user finds the right place to rent, they can simply (and safely) book and pay.

The Airbnb platform makes it simple to rent out your garden unit or coach house or guest suite or any space that you only use occasionally.

Here are the Airbnb benefits for Chicago property owners include:

  • Surge pricing for events, Seasons, and weekends
  • Supplemental income
  • Potential to meet guests from across the world
  • A nice place to house family and friends coming into Chicago

Airbnb guests get a local Chicago experience instead of being limited to hotels. This seems to be highly appealing to Millennials, but we've seen all ages use Airbnb to save money (versus a hotel) and stay closer to family/friends. Others look for truly unique accommodations in a home-like atmosphere. Here are some of the benefits:

  • Airbnb's safe vetting and identification process
  • More options in more Chicago neighborhoods
  • The LOCAL Chicago neighborhood experience
  • Unique buildings

Little-known Airbnb Gems in Chicago

Some Airbnb options fulfill your basic needs. You get a place to sleep, a kitchen, a bathroom — just the basics. Others go way beyond average with creative decorating themes, unique buildings and designer touches. While some people go for affordability, many want the experience of staying somewhere unique. The city has many of those standout options that solve the dilemma of where to stay in Chicago.

What are some of the top-notch Airbnbs in Chicago? Here are some unique offerings in the city:

Nestled in Southport Corridor, a short walk to Wrigleyfield, this duplex features two floors of newly renovated finishes. Equipped with 4 beds and room to sleep up to 10, you can find this home on a quiet one-way street only one block away from the Brown "L" stop.  Enjoy the fully-equipped kitchen and bathrooms before heading out to a Cubs game! You even get a personal parking spot in a gated area.

winchester chicago airbnb

Bucktown is one of the sought after neighborhoods for families and young professionals. It has some of the best food, coffee, and cocktail joints in the city.  This home is all custom-made. It even has heated floors in the basement!

From the outside, you see a quaint garden in the front and when you enter you can see that everything has been meticulously detailed. The architecture and detailing leave you in awe over this Bucktown home. The outdoor area is fully stocked with a grilling area, garden, sound system, and a nice little yard. This home is great for business traveling groups and families!

RIVER NORTH GALLERY on the Park w Parking

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The apartment is located in River North in Downtown, Chicago. It is in the Near North Side district, and as seen on the map below, in the River North area. There is a very prestigious high school (Walter Payton College Prep) closeby, town homes with young families and popular cafes and restaurants (Big and Little's) in the neighborhood.

It's the place to be! Formerly home to many factories, it's modern mix of high-rises and historical buildings adds to the neighborhood's eccentric feel. You can find some of the most popular restaurants, dive bars, lounges (nightclubs), jazz clubs and art galleries here. The area is ideal for a traveller. The apartment is near all major shopping and nightlife streets, while also being walking distance from Lake Michigan.

Airbnb Effect on Chicago Neighborhoods

Airbnb’s impact in Chicago is a top of debate among property owners, city government leaders and community members. The news in the beginning of 2018 says that Airbnb raised $2.9 million for homeless services.

Some argue that Airbnb rentals hurt the market.  They say that short-term rentals take away the option for longer term renters to claim space, leaving fewer rental options and driving up the prices. They also say that it takes away from the sense of community.

For these reasons, Chicago has put in regulations with the goal of keeping the sense of community and not driving up prices.

Proponents for Airbnb in Chicago know that the guests bring money into the Chicago communities where they are located. A visitor who might normally choose a hotel in the heart of Downtown Chicago instead chooses a unique rental in a lesser-known neighborhood. The restaurants, boutiques and other businesses in that area earn increased revenue as more guests stay in the area.

For Chicago property owners and investors, the home-sharing market offers a major benefit. In 2017, according to data from Zillow and Airdna, Short-term rentals on average made 40.1% more money than longer-term rentals. Airbnb investment properties give owners a major source of income to offset the cost of the mortgage. For homeowners who rent a room or the whole unit, home sharing is a way to supplement income or help pay for the home. For business owners with investment properties, it maximizes profits.

Chicago Regulation For Airbnb

While guests seem to want a more local experience through Airbnb, the growth has caused many cities to implement regulations. 

Chicago passed regulations in 2016, and a supplement in 2017, to better foster home sharing in Chicago. Airbnb property owners now must upgrade their homes and experiences. Some home sharing opponents feel there is room for more regulation. Here are some components of the regulations:

  • Extra tax on the income generated from the property
  • Cap on how many units in a 5+ unit building can be rented via Airbnb — 6 units or 25 percent of the total units, whichever is smaller
  • Requirement for hosts to keep records on guests
  • Inspections of rentals from building commissioners
  • Primary residence requirement for single-family homes and buildings with two to four units

Another component is the Prohibited Housing List. Essentially, the owner of a building can place units on the list, meaning those spaces are ineligible for renting on Airbnb. As of 2018, about 91,000 apartment and condo units are on the list. That may sound like a lot of units, but it’s only about 7.6 percent of all Chicago housing units, so there are plenty of properties not on the list.

The list of properties on the list is concentrated highly in the downtown area, especially for big condo buildings, although there are properties throughout the city that don’t allow home sharing. Always check before purchasing a property as a rental. No matter how tempting it is to rent out a unit for profit, ignoring the rules can result in fines of $1500-5000.

How to Invest in an Airbnb Property

Evaluate your readiness to jump into an Airbnb rental business with these questions:

  • Do you have the capital to invest or secure a loan for the property?
  • Can you cover the payments if you aren't able to rent out the place regularly?
  • Is the building suited to have short term rentals? (ie security, egress, maybe separate entrances)
  • Does your insurance allow for short-term rentals? (We know a few that do!)
  • Are you prepared for the possibility of damage to the property?
  • Do you want to manage all of the guests and increased turnover by yourself or with a management firm?
  • Do you know the latest regulations for Chicago Airbnb properties?
  • Do you have time to manage needy guests and bookings?
  • How much more income can you make, and is it worth it?
  • Will you handle cleaning, check-in and check-out, customer service and other issues yourself? If not, can you still make a profit when you hire someone to handle the work?

What makes a good Airbnb investment


Most Airbnb rentals in Chicago are unique. They stand out as an experience to remember rather than just a place to stay while in Chicago. When considering investment opportunities for Airbnb property in Chicago, here are a few factors to consider:

1. Location

Proximity to the downtown is the name of the game. Imagine you are at traveler who has never been Chicago - you don't know about the neighborhoods or local tastes. Airbnb guests in Chicago want proxmity and safety!  Look at the location from a traveler's perspective. They want neighborhoods that are safe, close to amenities and give them easy access to other parts of the city.

Distance to public transportation is not as important as you think. While it helps for business travelers,  it is not as big of an issue because Chicago has Uber/Lyft. That said, public transportation helps because renters want access any attraction in the city. Investing in a property with a prime Chicago location increases your chances of filling up your calendar with rentals.

2. Compliance

Regulations in Chicago can change at any time. Make sure a potential investment property meets current Airbnb regulations set by the City of Chicago. Ensure the property isn’t on the Prohibited Housing List. Verify that the building association or homeowners’ association doesn’t have restrictions in place on home sharing.

3. Amenities

What amenities does the property offer, or can you offer? Does it have outdoor space, a patio, a hot tub, a pool table, great views or a gourmet kitchen? What about parking? Those extra touches make your Chicago Airbnb more appealing to Airbnb guests who want a unique, homey experience. 

4. Size

This is a sleeper. The size of the unit is an important factor because the bigger the unit, the more people you can sleep. The more people you can sleep, the more money you can potentially make (as long as it is compliant with Chicago's fire code!). 

Some Airbnb guests want to accommodate a whole family. Others use Airbnb to find even larger spaces for reunions, retreats or other large-group travel. 

5. Style and Character

Chicago homes with classic character and unique style often gain attention on Airbnb because pictures are one of the most important parts of your listing. 

You don’t need to buy an old church to have a popular rental option. You might choose a modern-style loft space or a vintage apartment with exposed brick walls.

From long-term to short-term rentals?

If you’re a property owner in Chicago, upgrading your home with Airbnb travelers in mind can be a ticket to making more profits with Airbnb.  Simple cosmetic updates or renovations can make your Airbnb more appealing.

Here are a few ideas to boost revenue:

  • Simple Guest Amenities

Simple additions to your home make for great guests stays. Think of the things we take for granted at home, sometimes. Maybe a rain showerhead or free Wi-Fi and free parking? A fireplace? Coffeemaker? 

  • Outdoor Space for Summer, Spring, Fall

Any outdoor space from a balcony to a backyard is a value-add to be included in pictures and to be upgraded for a great guest experience. Add seating if the space allows. Other options to upgrade outdoor spaces include plants, BBQs, hot tubs, and gardens.

  • Nice Finishes

You don't need to do a full renovation, but guests want to stay somewhere nice and clean. Take time to upgrade the kitchen, common areas, and any part of the property that guests may become attune to. 

  • Create Your Own Theme

You'd be amazed what some art and knick-knacks can do for your place and for the photos. Add some decorative touches to give it a distinct theme. If your space is an industrial-loft, play up the contemporary industrial vibe in your color choices, furniture and decorations.

  • Home away from home :)

How can you make your airbnb homey and have your guests feel like they are home away from home? Adding little accents that make it feel more like home help a lot! Hang artwork on the wall, places flowers in a vase and display coffee table books in the living room. Simple touches make a big impact.

One way to identify upgrades you need to make is to spend the night in your own rental from the perspective of an Airbnb traveler coming to Chicago. If you were to rent that space for a vacation, what would you like? What would you dislike? What would you change? 

What do you think of our guide to the growing Airbnb market in Chicago? It seems to continue to grow so don't get in too late! 

For the local Chicago Airbnb Experience: Chicago's most secret bars


You can do a Google search and find most of Chicago's hidden speakeasies, but can you actually get in? How easy is it?

From romantic cocktail hangouts  to Irish dive bars, here's how to access top secret bars all over Chicago when you are coming to Chicago for your Airbnb experience.

Local Airbnb Travel Experiences in Chicago


The Library at Gilt Bar

If you’re looking to get intimate somewhere dark and cozy for the evening, try to find the Library in River North. The sexy subterranean bar is located just below Gilt Bar, but chances are you’ll need some serious help finding the hidden doorway.

Before you go, here are a few things to know: The space is only open Thursday to Saturday starting at 6pm. They take reservations. When you arrive at Gilt Bar, let the host or hostess know that you’re heading down to the Library and they will show you the way. Once you’ve made it inside, you’ll be rewarded with plush red banquettes, candlelight, classic cocktails and Gilt Bar’s full menu.


The Drifter

Green Door Tavern is one of the oldest bars in the city, and in River North. The bar’s basement speakeasy, the Drifter, is a cocktail haven that only requires a little patience to find. 

Here's what you'll do: Walk into Green Door, head to the back of the bar and hang a left to go down the stairs as if you were going to the bathroom. At this point, you may encounter a line for the Drifter. If not, look for a knickknack-adorned door at the bottom of the stairs. Once inside, you’ll be handed a few tarot cards, which double as the cocktail menu. It’s all luck of the draw. 


Booze Box

The West Loop is full of industrial-masked, hidden surprises. From the outside, you wouldn’t guess that Sushi Dokku in West Loop has something to hide, but insiders know it is a special treat.

You’ll feel like a covert spy  for boozy cocktails and quality hip-hop music once you land inside Booze Box. Head to the alley just behind Sushi Dokku and look for the red light above a door—you've successfully found Booze Box. If you can’t find it, the staff will be happy to escort you downstairs. 

Fifth Province Pub

Irving Park’s Irish American Heritage Center houses a library, a museum, an art gallery, an auditorium and a banquet hall, but you can also stop by for a drink at its authentic Irish pub. It’s easy to get into—just walk in through the building’s main entrance take a left and you’ll soon find yourself in a bar called the Fifth Province. You can order a pint of Guinness, sip on some whiskey or dig into a giant basket of steak fries.

It’s a popular destination for Irish tourists and musicians playing traditional Irish music—if you’re lucky, you’ll overhear someone speaking with a genuine brogue.

The Pub at U of Chicago

If you're up for a challenge and an adventure, the members-only Pub at the University of Chicago is perfect for you. To get there, walk into Ida Noyes Hall, turn left and go down the stairs. You'll be deposited in a nondescript hallway, to the right is the Pub.

The bar itself has a tiny entrance, so "sneaking" in is truly impossible. Instead, stand outside and wait for members to arrive and politely ask a friendly face to be your escort in. It'll cost you a $3 cover and a peek at your ID. Just be sure to buy your host a beer once inside as a token of your gratitude. But believe us, the beer selection and the nachos are worth it.

For a true Chicago Airbnb nightlife experience, try these hidden bars and tell us what you think!