Chicago
United States / North America
Overall score
Quality of life score
Good
Family score
Good
Cost
Internet
Fast: 45Mbps (avg)
Safety
Good
Top Ten
Restaurants
1. Oriole
3. Joe's Seafood, Prime Steak & Ston...
6. Wildberry Pancakes and Cafe
8. Steak 48
Attractions
1. The Art Institute of Chicago
2. Museum of Science and Industry
3. 360 Chicago Observation Deck
4. Cloud Gate
6. Field Museum
10. Lincoln Park Zoo
Triploaf Picks
Architecture Boat Tour
This bad ass tour will take you through the Chicago river but give you some history and really informative information about Chicago's skyline. Its one of the best tours I have done. Not for the winter though.
Harold's Chicken Shack
Who like fried chicken? everyone but a vegan! Harold's is great and you'll lick you're fingers when you're done.
Milenium Park
Take a stroll through the world-famous Millennium Park. (You could even do this while waiting for a table at Wildberry.) Some notable sites to visit are Cloudgate (a.k.a. the bean as the locals call it, be sure to flick it), Jay Pritzker Pavilion (a beautifully futuristic amphitheater), Buckingham Fountain (one of the most stunning and grand fountains in the world-there are night light shows as well), Crown Fountain (a popular fountain for children to play in on a hot day, two faces are shown on giant screens and if you wait long enough they’ll even shoot water out of their mouths). There are also many other parks, trails, and even a roller rink to get lost in. We actually ended up at Millennium Park multiple times! There are also sometimes great events taking place. When we visited there was Jazz Fest which was free for the public to enjoy.
The Doughnut Vault
Something about these doughnuts that is just epic. I LOVE them and you should too! The bakery is small, all doughnuts and made in house. The menu changes daily and theres always a line so try to get there early. Get some for the ride back home and some for afternoon snack. The old fashioned glaze doughnut has to be the best in the country.
Jimmy's Red Hots
Polish Sausage. Does anything more need to be said? I like my meat in tube form. Jimmys is a Chicago staple, amazing steamed bun with polish sausage topped however you would like. Order a hotdog and cant forget some fries. Cash only establishment!
The Green Mill
Al Capone’s favorite bar back in the day. This historic Blue/Jazz club should not be overlooked and should definitely take participation in your life. Cocktails and entertainment are served... Best Gin Martinis!
Architecture River Cruise
Close to the riverwalk you can join an Architecture River Cruise, which was recommended to us by everyone who has visited Chicago and even by locals. A lot of people recommend going for the sunset cruise at it offers some picturesque views of the city with beautiful lighting. We elected to use First Lady Cruises, as suggested by friends, they offered a lot of departure times and left from the Riverwalk as opposed to Navy Pier (which we were told is the worst tourist trap you can visit in Chicago). The architecture river cruise is fascinating and very enjoyable as Chicago has some of the most beautiful and historic architecture in North America…there is also a bar onboard because any cruise is a booze cruise if you try hard enough! You can buy your tickets online for a discount and avoid the ticket counter lines.
Big Star Tacos
Located right off the Blue Line at Damen station, it's a hoppin joint that makes amazing tacos and has great beer and cocktails. It's a spot I ALWAYS visit when i'm in Chicago and a place you need to make a point to visit. It also gives you an insight into the Wicker Park Neighborhood. The tacos are the best in the midwest and easily compare if not better than LA Taco Trucks.
Weiner's Circle
Looking for a hot dog? well there is a lot of yelling here and the dogs are good but the energy and insults coming from the employees directed to their customers are better! It will provide you a small smile and entertainment. Warning: Profanity and laughing happen here.
Lou Malnati's Deep Dish Pizza
Chicagos legendary deep dish pizza. The pizza is flippin amazing! the salads are to die for. The dressing is a secret recipe that i want stocked in my fridge always! Make sure your schedule is light the rest of the day. Must Try: Get some chicken wings and try the thin crust pizza that is actually pretty good.
The Signature Lounge
The John Hancock building has a great cocktail lounge appropriately named "The Signature." You can skip the line and "the tour price" if you go and have a cocktail at the top of the John Hancock building to catch a view of Chi-City. I recommend doing this before the sunset and get there a little early as the lounge is a first come first serve seating and the sunsets are spectacular.
The BillyGoat Tavern
CHEEZBORGER? No PEPSI.....COKE! Get yo-self a cheeseborger and a coke and enjoy. you can now find these all over Chicago. This place has a long history in Chicago stemming from the now famous skit performed by John Belushi 30 + years ago. So check out the SNL skit then go grab a drink and a borger . Take in and appreciate the history of it.
L & L Tavern
Get yourself a "Marlot." Something that is specific to Chicago. I loved that Anthony Bourdain Found this incredible dump interesting. Sit back, watch and listen and you will see what makes this place interesting.
Public House
A gastropub and sports bar. A great place to come and thrash your stomach. You'll love it!
The Second City
Hands down some of the best improv comedy...EVER! Many, many big names have come through and graduated onto the big screen and SNL. Your going rip yourself new stomach muscles after a night here from laughing.
Sluggers
Wrigglyville has a lot of fun bars and gastro pubs all right by Wriggly Park, home of the DAAAAAAH CUUUBS. But this bar has an upstairs with a batting cage in it along with a bunch of other fun arcade games. You'll want to make a stop here.
Old Town Alehouse
Something about this dive bar that makes it special. come in for a pint and don't leave for awhile. One funny thing about the Ale House is that owner has a "No Shot" list. Instead of getting kicked out at first, he just puts you on the list [and you can’t order shots]. So much character in this bar, from the paintings to the people you will meet.
The Publican
This is a place that should have itself a michelin star. You'll enjoy every meal available to you. The Publican is a European beer hall where you can gather and share food with your friends. They specializes in beer, pork, and oysters. The thick wood tables and furnishings will remind you of Game of Thrones.
The Library
The Library is a hidden gem located under the Gilt restaurant. See a hostess at the Gilt who will hopefully have space for you downstairs in the hidden speakeasy. The hostess will guide you downstairs towards the restroom in a hallway filled with photobooth pictures and will then surprise you with a secret door that leads to an intimate cocktail lounge and restaurant. With jazz music filling your soul and wonderfully perfected craft cocktails all while feeling in a dream-like state with the candlelight, you’ll quickly realize this place is a hidden gem.
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