Headquarters Beercade
Nightlife
10
3
Even though a few places like this are springing up across the country, it's still a pretty novel idea, and one of the biggest venues of its kind. You'll get to enjoy all those throwback arcade games without having to pay for them. Whether it's Mortal Kombat, Street Fighter, Pac-Man, Time Crisis, or Pinball, plenty of classics are covered. Game on!
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Chicago Athletic Association Hotel
Nightlife
12
3
To validate your class, yes I said that! To play pool, "Go Thorsten Hohmann (google him), shuffle board, chess, or bocce bay all while having the option of ordering food and drink. They have a rooftop area with a gorgeous view of the city and lake.
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Local Experience
Private Chicago Photo Shoot Tour
Prices from
40
USD
Duration
1 h
Languages
English
Hopleaf Bar
Nightlife
11
4
This is one of the most local feeling bars in Chicago. You can defiantly pick out the regulars by the way they interact with the waiters and bartenders. It defiantly has a community feel. Plan to see other parts of Andersonville during your visit since Chicago is a large city and distances can seem shorter than they are in reality.
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The Second City
Nightlife
12
4
This is where many of the most famous comedians had their start. Tina Fey, Stephen Colbert, Steve Carell, and Amy Poehler, just to name a few. Chicago is also the birthplace of modern improv comedy. You'll have great laughs, enjoy drinks, and get involved with the show if you're seeing an improve show. Definitely a must visit.
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Pequod's Pizza
Eating
15
4
Their deep dish pizza is baked in a pan lined with cheese, which leaves a delicious carmelized crust along the edges of the crust. You'll avoid the huge crowds at places like Gino's East, Lou Malnati's, Giordano's, and Pizzeria Uno (all great, but very touristy). It spans two floors, and the seating area runs deep into the building.
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City Winery Chicago Riverwalk
Eating
15
4
You should go for the great view of the river and great wine. The Riverwalk has been newly renovated so it still has the "new and shinny" feel. You can come here for a meal or just for drinks. I would recommend going early-ish to be the crowd since the place has become very popular
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Local Experience
Private Chicago Photo Shoot Tour
Prices from
40
USD
Duration
1 h
Languages
English
The Publican
Nightlife
10
1
You should visit to try their amazing culinary skills and be absorbed in the trendy atmosphere. Experiencing this restaurant is very defiantly a unique experience. The locals like it so much they have their weddings in the restaurant!
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Green Mill Theater
Nightlife
17
4
It is the most popular place for music in Chicago. Chicago artists themselves come to this joint to appreciate true talent. It is known all over the world however it still manages to give you the feel of an intimate bar and well kept secret by locals.
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Three Dots and a Dash
Nightlife
7
3
Because it is the famous Three Dots and a Dash Lounge. Perfect for birthdays to give it a fancy twist. 2nd or 3rd dates where you intend to really get to know your date. And the drinks are strong and tasty and interesting. Drink out of a skull, a shell or fire... Everything thematic about this place and its built to impress
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The Signature Lounge
Eating
8
3
There is no fee to enter The Signature Lounge and the price of a drink is cheaper than a ticket to see the view at Willis Tower (no bar at the top of the Willis Skydeck). If you want to get the most of the Chicago skyline come to this lounge for sure.
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Masada
Nightlife
3
1
You should visit for the entertainment! Last time I made it to Masada a the music changed and a belly dancer with a candelabra with lit candles on her head. You should go to see a different style...a modern middle eastern style
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The Violet Hour
Nightlife
3
0
This bar is the epitome of dark and stormy. It's great for quiet conversations while you and a date get tipsy. Every drink on the menu is worth the price (typically $12), but you can't go wrong with the Lazarus Reviver (stellar gin drink).
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Empty Bottle
Nightclubs
2
0
When I go to the Empty Bottle I go as a wing-woman for my single friends and we dance the night away as we check out the handsome men. It's a great place to grab a beer with someone new. This venue has a very local vibe so come here if you want to dance with a local.
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Winter's Jazz Club
Nightlife
3
0
Baffled at how they have never heard of it yet or that it is the name that is trickling & tickling musical ears around town. Acoustics: well placed, technology is so new, and the place isn't boisterous so you feel like you are among the select few who get to watch the best Chicago musicians up close. The walk in is out of the ordinary & romantic
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Lottie's Pub
Eating
5
1
Lottie was a transvestite. This info is 2nd-hand from a tour, Drinks W Locals & Travelers by Marco of LikeALocalGuide. Lottie held underground/bar activities & eventually got busted for. The bar closed down in 66' and Lottie was long gone. They reopened in 2000's and say her ghost looms the scene happy that customers still have a good time.
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