Best Chicago Speakeasies

Everyone likes to be in on a secret. It’s an exhilarating feeling – you’re special, knowing something your coworkers, family or friends don’t. It’s even more exciting knowing a city’s secrets, and trust us when we say Chicago has plenty. Our Free Chicago Walking Tours are loaded with them. When most people think of a night out in Chicago they think of well known areas like River North and Gold Coast–perfectly fine choices no doubt, but what they don’t know is that Chicago has some of the best hidden bars in the country. You can find speakeasies in the strangest locations throughout the city. It’s also a great way to explore new neighborhoods in Chicago. Keep reading to see which bars you cannot miss out on while in Chicago!

Violet Hour

1520 N. Damen, Chicago, IL (Wicker Park)

original_TVH_JohnHerndon__CassandraStadnicki

Source: The Violet Hour

Perhaps one of the most famous bars in the city, The Violet Hour may also be one of the classiest. Located in the bumping and trendy Wicker Park neighborhood, The Violet Hour will make you feel like one of Chicago’s elite. The Violet Hour has no door, sign or light. If you’re not careful you will walk right past the door which is typically painted over and a part of a larger mural that covers then entire front of the building. After ten minutes a bouncer will take you into a waiting room– a sign that you’re in. You must adhere to the strict dress code, never order anything that you’d drink at a frat party and refrain from using your phone.

What you need to know: No reservations. No use of cell phones inside. No baseball hats. No reservations, first come first serve. No ‘O’ bombs or jaeger bombs or any kind of bombs. No Budweiser.

What you need to try: Frites and aioli for a snack and wash it down with their version of a Manhattan – appropriately called Brooklyn.

 

Booze Box

823 W Randolph St, Chicago, IL (West Loop)

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Source:Sushi Dokku

Many people have heard of the restaurant Sushi Dokku in West Loop. It’s located in the arguably the hottest restaurant “district” in Chicago today. Sushi Dokku has neighbors with names such as Au Cheval, the Girl and the Goat and The Publican. Randolph Street is a gem amongst the restaurant and bar world of Chicago. But we digress. We’re talking about Booze Box here, the bar in the basement of Sushi Dokku that many that have dined there don’t know about. You have to walk 10 yards south to an alley behind Sushi Dokku where you will see a lonely bright red sign– the entrance to Booze Box. The atmosphere and what they are serving is just as unique as their entrance. Japanese street food, cold draft sake and a rotation of DJs spinning next to the guests at the bar all make a visit here worthwhile.

What you need to know: Booze Box is open only on the weekends – Thursday, Friday & Saturday – starting at 6pm.

What you need to try: Chill Gin Mojito

East Room

2354 N Milwaukee Ave, Chicago, IL (Logan Square)

eastroom

Source: Yelp

To be fair– East Room isn’t a speakeasy all the time. They open their doors to the main street when there is a special event or concert, but all other days you can only get in through the back door. The first time we went there it took us 20 minutes to find the place. Your phone will be telling you you’re standing right in front of it but you won’t see a soul near you. Everyone will be across the street at all the other bars lined up pretty in a row. But don’t give up! Just walk to the back alley until you see a strong looking man leaned up to the wall. He is your way into the second floor– a mix of cheap drinks, good music and wooden benches for good conversation.

What you need to know: Cash only! So, you know…bring cash or someone that has cash.

What you need to try: BYO-Vinyl. Yes, Bring Your Own Vinyl, as in records – East Chicago crowd-sources their music on Mondays.

 

3 Dots and a Dash

435 N Clark St, Chicago, IL (River North)

threedots

Source: Facebook

Consider this a new-age speakeasy. A new-age tiki-lounge-inspired speakeasy. This place is far from your traditional prohibition-era underground hush hush place. It’s still more well known than the other bars, but 3 Dots and a Dash is one of the funnest speakeasies in town. It boasts a Polynesian type theme complete with mini umbrellas in the drinks and almost any type of rum you could possibly dream of. You’ll often see large 21st birthday parties, bachelorette parties and groups of bar crawlers. This is a great speakeasy to have a drink at before hitting the clubs in the area.

What you need to know: It’s tricky to find. Walk up Clark St, then head east on Hubbard and go north up the alley. On your left (west) will be a small hanging sign that says “3 Dots and a Dash” – congratulations, you have arrived.

What you need to try: For those in a large group or with plenty of disposable income – or both, you definitely should order the “Treasure Chest” – a $400 cocktail that is served in a actual treasure chest on bamboo shoots carried in by a couple of waiters. Smoke (dry ice) billows out, the drink is lit up and the waiter pops a bottle of Dom Perignon and pours it into the concoction. Everyone at the table gets a giant straw and has at it.

Door No. 3

1572 N Milwaukee Ave, Chicago, IL (Wicker Park)

door3

Source: Facebook

Another speakeasy located in Wicker Park, Door No. 3 puts you in the mood with a secret entrance in the alley behind the Damen Blue Line stop. What makes Door No. 3 special is the live music. The DJs are skilled spinners that know how to keep people dancing and keep the party going. The interior isn’t shabby either with sexy leather furniture and blue lighting perfect for a chill, relaxed date night. It is also a go to destination to kick off a night of bar hopping in Wicker Park.

What you need to know: There is no food served here. They have a small vending machine   in the corner to satisfy your hunger. They aren’t known for any fancy cocktails either. Hipster beers like PBR and Tecate are available as well as your traditional mixed drinks.

 

Room 13

3222 N Sheffield Ave, Chicago, IL (Lakeview/Wrigleyville)

room13

Source: Old Chicago Inn

No questions about this one – Room 13 is definitely a speakeasy. Or maybe it should be a “speak hard” because it’s not easy to get into. Get it? Ha.

Located a half a mile south of Wrigley field like many speakeasies Room 13 is a part of another business: The Old Chicago Inn Bed & Breakfast. This place has all the markings of a speakeasy. Garden unit, check. Classic American cocktails, check. Dress code, check. Oh, and you seriously need to work to get in.

There are 3 options and only 3 options to get into this place:

  1. Stay at the Inn and you will receive an invite
  2. Buy a membership (aka become a member)
  3. Be a guest of a member

Mic drop. That’s it. If you are not fitting into one of those buckets you will not get in.

What you need to know: This place is seriously awesome.

What you need to try: Their cocktail flight. Reserved exclusively for guests of the Inn simply add the “Speakeasy Flight” to your reservation and you will receive a flight of 4 cocktails while the bartender explains the history of each drink. Cost is $55 for two people.

The Office

955 W Fulton Market, Chicago, IL (West Loop)

office

Source: Yelp

Ah yes, The Office. This will be sort of a good news – bad news situation. Let’s start with the bad news. This is another really tough one to get into. The good news? It’s underneath one of our favorite bars in the city which you can get into (if you have a reservation): The Aviary.

The Office is a 14-seat VIP speakeasy located beneath The Aviary. The bar features drinks and food that you will not find on The Aviary’s menu. If you’re a commoner just having drinks and food upstairs you might notice people going in and out of The Office and wonder – how do I get in? Well…you need to be invited. The staff at The Aviary invite guests to The Office. That’s it. Good luck!

What you need to know: If you have made it inside The Office and have to use the bathroom you’ll take a key from the bar, use the “commoners” restroom and get back inside The Office using the key.  And it’s not exactly cheap either. $20+ cocktails, $30+ appetizers, Make sure you bring your wallet!

What you need to try: The level of attention you receive from the staff and bartenders is incredible here. Instead of ordering off the menu tell the bartender your favorite spirit and let them come up with something that will impress. And if you’re in mood the mood for desert order their ice cream sundae. OMG.

If you have the time give all of these spots a try while visiting. And let us know in the comment section how the night went. We look forward to hearing from you!

Chicago Neighborhood Guide: Andersonville

Getting to Andersonville

Andersonville is one of Chicago’s great neighborhoods.  Located on Chicago’s far north side, it is easily accessible by public transportation.  Using the city’s “L” train, take the Red Line to the Berwyn stop or the Bryn Mawr stop.  From either stop, it’s just a 10-minute walk west to downtown Andersonville.   You can also catch the #22 city bus, disembarking at any of the stops along Clark Street, between Foster Avenue, which borders Andersonville on its south end, and Edgewater Avenue, which borders Andersonville to the north.

If the weather cooperates, you can get around by bicycle.  Consider taking advantage of Divvy, Chicago’s bike share system.  There’s a station conveniently located at the intersection of Clark St. and Bryn Mawr Ave.  But don’t worry—When the weather isn’t bike-friendly, cabs are always plentiful.

Andersonville History

Andersonville dates back to the 1850s, when it was settled by Swedish immigrants.  There are still plenty of signs of Andersonville’s Swedish heritage.  Andersonville celebrates its Swedish roots with Midsommarfest, an annual summer street festival.  The south end of Andersonville is anchored by The Swedish American Museum and features several businesses with Swedish roots, like Svea Restaurant and The Swedish Bakery.  The Swedish Bakery makes some of the best pastries in the city, including an assortment of Swedish pastries.  Be warned that The Swedish Bakery is closed on Sundays!

Andersonville is home to one of the largest LGBT populations in Chicago.  It boasts several gay bars, including @mosphere, The Call, and Mary’s Attic.

Andersonville in 1 Day

If you only have one day to spend in Andersonville, consider these suggestions, all of which are located along Clark Street, Andersonville’s main drag.

Start your day on the north end of Andersonville, with breakfast at m. henry (5707 N. Clark St.).  This breakfast, lunch, and brunch spot is insanely popular.  If you want to enjoy a classic weekend brunch, arrive very early or face a 90-minute wait.

After breakfast, enjoy Andersonville’s shopping scene, which is refreshingly void of any big chain stores.  Just north of m. henry, you’ll find Gethsemane Garden Center (5739 N. Clark St.). Even if you’re not into gardening, you’ll enjoy its Wild Pansy Gift Shop.

andersonvilleshopping

Moving southwards on Clark Street, you’ll find a dizzying array of independently-owned home furnishings and antique shops, like Roost (5634 N. Clark St.) and Room Service (5438 N. Clark St.).  You’ll also find fabulous gourmet food and wine shops, like City Olive (5644 N. Clark St.) and In Fine Spirits (5418 N. Clark St.).  Fans of Italian food will enjoy Piatto Pronto (5624 N. Clark St), a grocery and deli carrying Italian imports and the biggest, most delicious, and best-priced deli sandwiches in the city.

If you’re in the mood for a sit-down lunch, stop by Big Jones (5347 N. Clark St.) for U.S. coastal southern cuisine. Start with a Pickle Tasting (a sampling of homemade pickles and home-baked Sally Lunn bread) and an order of fried green tomatoes.  For your main course, enjoy Big Jones’ award-winning fried chicken or an order of shrimp and grits.  Lunch is available Monday-Friday only.  If you come on a weekend, enjoy a Big Jones brunch from 9.am. – 3 p.m.

After lunch, enjoy a mani/pedi at 2×10 Nails (5414 N. Clark St.).  If that’s not your thing, while away the afternoon browsing more of Andersonville’s locally-owned shops.  Vinyl lovers will appreciate Borderline Music (5351 N. Clark St.).  Book lovers will enjoy Women & Children First, an independently-owned bookshop (5233 N. Clark St.) specializing in feminist and children’s books.  This shop is a gem if you’re looking for a gift, but aren’t sure what to buy.  Their sales staff makes excellent suggestions and complimentary gift-wrapping is offered.

No trip to Andersonville would be complete without a trip to Andersonville Galleria (5247 N. Clark St.), a retail building that houses 90+ tenants.  Its tenants are local artists and entrepreneurs, selling everything from jewelry, gourmet treats, unique homemade gifts, and more!

Care for a cocktail before dinner? Stop by Marty’s Martini Bar (1511 W. Balmoral Ave., just one block west of Clark St.) for an expertly-made cocktail.  Warning: Marty’s is small and extremely popular, so arrive early!

Andersonville has an enticing array of restaurant options.  For an upscale dinner that isn’t at all stuffy, choose Anteprima (5316 N. Clark St.).  Anteprima services seasonal Italian cuisine, complemented by a full bar.  The dinner menu features standouts like Arneis Braised Rabbit and Grilled Lamb Leg.  Anteprima emphasizes fresh, seasonal ingredients, so the menu changes often.

Free Chicago Walking Tours Andersonville Food

For a more casual dinner option, choose Jerry’s Sandwiches (5419 N. Clark St.)  Jerry’s Sandwiches features 100+ sandwich options and offers even more craft beer choices, many of which are made right in Chicago.

After dinner, head over to Mary’s Attic (5400 N. Clark St.), which is the 2nd floor of Hamburger Mary’s Restaurant. Mary’s Attic is a bar featuring an ever-changing menu of entertainment options, like live bands and MaryOke (karaoke).  Straight people are welcome at this establishment/gay bar.  Or if you’re in the mood for comedy, check out The pH Comedy Theater (1515 W. Berwyn, one block west of Clark St.).  This comedy theater offers a wide variety of comedy shows…improv, standup, sketch, and musical.  Its shows come “For the Family,” “PG13,” or “Adults Only.”  Check out their website www.whatisph.com for a schedule.

Andersonville…a fabulous neighborhood with something for everyone!

12 sites to help you plan an unforgettable visit to Chicago

Chicago is a massive city – covering over 237 square miles. There are roughly 2.7 million permanent residents and more than 48 million visitors to the city each year. There are almost 5,000 restaurants to choose from. You could visit a different museum every weekend and still have leftovers, because we have 60 of them – including the #1 Museum in the World. (spoiler: Art Institute of Chicago). There are over 200 theaters & over 225 music venues in Chicago. Getting around in the city can be a breeze or you could feel like it requires an advanced physics degree. Chicago has 28 bus routes & 8 train routes that connect 146 stations. Over 3,000 bikes spread amongst 300 stations are available to rent by the hour to help you tackle one of the countries most bike-friendly cities. And while Chicago ranks #3 by population in America we’re still home to 8,1000 acres of green space, 580 parks and 26 beaches.

Source: City of Chicago

So how the heck are you supposed to figure all of this out on your short weekend trip or heck, even week-long trip to Chicago? Free Chicago Walking Tours is going to help. We present to you the top 12 resources to “hack” your way to an unforgettable Chicago vacation. These websites are a special selection that will make you you make the most of your Chicago trip by having fun, learning & meeting people.

START HERE WITH THESE GENERAL TRAVEL & CHICAGO SITES

TripAdvisor Chicago – Hear us out first. Free Chicago Walking Tours recommends using TripAdvisor Chicago as a way to start the brainstorming process and see what other visitors did in the city.  There is so much information in one place. From things to do, to restaurants, hotels and short-term rentals. Free Chicago Walking Tours even challenges Chicago-area locals to take a look for themselves and find out what is hot in Chicago.

Wikitravel Chicago – Online since 2003, Wikitravel bills itself as the original crowd-sourced travel guide with over 300,000 destinations, including Chicago. There is so much information here. Free Chicago Walking Tours loves this information because it really doesn’t come with an agenda. It’s simply there – use it as you please. It coves topics you really won’t find on other travel sites. Topics such as staying safe within the city and includes a listing of all of foreign consulates located within the city as well as their address and phone numbers. But there really is so much more than this. if you have an hour or so to spare and have never been to or read about Chicago you must visit this page.

Choose Chicago – Yes, we know. Not really a hidden gem or a secret, but this is a catch-all site that is dedicated to Chicago and it didn’t feel right leaving it off. Choose Chicago has a little (OK, a lot) of just about everything. It can be a bit overwhelming because there is so much information, but used correctly and it can be a real asset. Their Chicago Trip Planner is an excellent place to start for those visiting for the first time or the fifth time.

OVER 30% OF VISITORS TO CHICAGO SAY “CULINARY EXPERIENCES” ARE THEIR PRIMARY REASON FOR THE VISIT. THESE SITES WILL MAKE SURE THOSE EXPERIENCES ARE UNIQUE AND MEMORABLE.

Eater Chicago – If you’re looking for the scoop on Chicago dining, drinking, food and nightlife check this site out. If you’re local and haven’t heard of it then you’re going to have some fun for a few hours. If you’re visiting and want to get down to the nitty gritty here are the best features for you:

  • Eater Chicago Essential 38 Restaurants (the answer to: “Can you recommend a restaurant?”
  • Eater Chicago Heat map (hottest Chicago restaurants)
  • We can’t link to this one, because it changes every weekend. But Eater Chicago has a feature every Friday & Saturday they present the best restaurants in Chicago with last minute reservations available from Open Table. Check it out when you’re in need of a place to eat but completely forgot to reserve your spot.

LTH Forum – This is a legit foodie website. It’s not flashy. It’s not sexy. It gets right down to business. The site is the work of Chicago locals who left another “more restrictive” food blog to start their own. Whether you want to meet up with locals to break bread together or you’re interested in getting the scoop on some neighborhood haunts – check this site out.

WEATHER AND TRANSPORTATION ARE TWO VERY UNPREDICTABLE ASPECTS OF CHICAGO LIFE. USE THESE SITES AND APP TO HELP YOU PLAN AND PREPARE FOR ANYTHING.

Spot Hero – For anyone that is going to be driving and parking in Chicago. This is the app for you. It’s almost too good to be true. You plug in where you need to park (an address, landmark, whatever) and the date range. Next thing you know it’s telling you all the spots – both public and private – that you can park at, their location and their price. That is it. Search for the spot, find the spot and pay for it.

RideScout – The all-in-one-whatever-mode-you-want-to-travel transit app has arrived to Chicago. Yay! This app will help you get from point A to point B. Whether you want to take a taxi, a bus, walk, bike, car share, park your care or whatever. All in one simple screen. This is great for those that want to take advantage of every single type of transportation possible in a city (you know who you are) and for those looking to take the most efficient route because they’re running late. Or for those that just want to see how close their friends can guess as to the time difference between taking a bike vs a ride share. Have fun.

Chicago Pedway – Wait, what’s a pedway? It’s a noun -a footway built for pedestrians in an urban area. In Chicago’s case it’s an underground pedway. But why you may ask? To help give you cover for our awful Chicago winters. Many locals don’t even know about it. Now you’re in-the-know. It’s sort of a tangled mess of underground walkways, but we have to admit it’s quite unique and if you have time (or for some reason you’re visiting in the winter) make sure you take a visit.

Dark Sky – Chicago is the Windy City. You have probably heard all of the silly one-liners. “If you don’t like the weather in Chicago, wait 15 minutes.” Chicago has four distinct seasons and then some. Cheers to Dark Sky and the technology behind it that can alert you down to the minute (not kidding) when it will rain or snow in Chicago.

CHICAGO ENTERTAINMENT. ENOUGH SAID.

Free Museum Passes from the Library – Sorry out-of-towners, this one is strictly for locals with a valid ID and Chicago address only. We just couldn’t leave it off our list though, it’s too good. This might even be the last drop in the bucket to motivate you to pack up and move to Chicago.

Just like the link says, if you have a Chicago Public Library card you can “check out” passes to the museum good for up to two adults. The catch? You MUST be accompanied by a child under the age of 18. And yes, the #1 Museum in the World is on the list.

ChicagoPlays – Remember those 200+ theaters that were mentioned in the opening paragraph? ChicagoPlays will make it much easier for you to navigate all that is happening in Chicago. Find a theatre. Find a play. Look by date. Look by what is hot. Buy Tickets. Have fun.

Did we miss a great site that needs to be added on this list? Let us know by adding your comment below.