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
Nightlife
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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Local Experience
Private Chicago Photo Shoot Tour
Prices from
20
USD
Duration
1 h
Languages
English
City Winery Chicago Riverwalk
Nightlife
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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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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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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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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Local Experience
Private Chicago Photo Shoot Tour
Prices from
20
USD
Duration
1 h
Languages
English
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
Things To Do
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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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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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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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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London House on 22nd
Things To Do
3
1
LH is a historical building, positioned strategically so you fall in love with the river&architecture. You're Surrounded by a panoramic "quiet" & behind the scenes is the charming Chef Riley Huddleston & his team athletically creating your culinary encounter with hand picks from all over the world, to assure you that times stops and you just live.
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Lottie's Pub
Nightlife
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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Monk's Pub
Nightlife
3
1
They have filling food. Cold Beer. And its the best bar closest to the Thompson Center where most train lines are. It is packed after work hours everyday but it doesn't give you that annoying "too many people feel." Instead It is bustling with the happy energy of loop professionals and the bar gives free peanuts that you can toss on the floor.
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Best Intentions
Nightlife
1
0
Authentic and genuine atmosphere
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