Guidebook for Chicago
Food Scene
Order the Mayan Mocha (iced or hot) for a one-of-a-kind coffee drink. Sit outside on the patio, sit at the coffee bar, or go upstairs to the quieter level. Great for people watching and eclectic music!
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Star Lounge Coffee Bar (Dark Matter Coffee)
2521 W Chicago AveOrder the Mayan Mocha (iced or hot) for a one-of-a-kind coffee drink. Sit outside on the patio, sit at the coffee bar, or go upstairs to the quieter level. Great for people watching and eclectic music!
Go for the tacos but you'll never leave with the margaritas or micheladas.
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Big Star
1531 N Damen AveGo for the tacos but you'll never leave with the margaritas or micheladas.
My go-to spot for getting work done. Mary and the rest of the staff are great. The turkey pesto sandwich is delicious.
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Lovely Kitchen & Cafe
1130 North Milwaukee AvenueMy go-to spot for getting work done. Mary and the rest of the staff are great. The turkey pesto sandwich is delicious.
Go here for the drinks, food, or both! They're well known for their game meats, so be adventurous! During happy hour, they have half-off oysters!
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Frontier
1072 N Milwaukee AveGo here for the drinks, food, or both! They're well known for their game meats, so be adventurous! During happy hour, they have half-off oysters!
My favorite ramen spot in the city. The caveat is that the line can be horrendous because it's a small little nook in the basement of Green Street Meats. Try and get there early (5pm) to put your name on the wait list and enjoy some beers at Green Street Meats while you wait. Or, go at the end of the night!
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High Five Ramen
112 N Green StMy favorite ramen spot in the city. The caveat is that the line can be horrendous because it's a small little nook in the basement of Green Street Meats. Try and get there early (5pm) to put your name on the wait list and enjoy some beers at Green Street Meats while you wait. Or, go at the end of the night!
The ice cream is really great here. Just watch out for the long lines.
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Jeni's Splendid Ice Creams
1505 N Milwaukee AveThe ice cream is really great here. Just watch out for the long lines.
Great pizza and you can order it for pickup or delivery. New Haven pizza, which is unique. Awesome atmosphere and a wide selection of beers from their microbrewery.
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Piece Brewery
1927 W North AveGreat pizza and you can order it for pickup or delivery. New Haven pizza, which is unique. Awesome atmosphere and a wide selection of beers from their microbrewery.
Must go! Get brunch, drinks or dinner or just some donuts out the back. It's all amazing.
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Longman & Eagle
2657 N Kedzie AveMust go! Get brunch, drinks or dinner or just some donuts out the back. It's all amazing.
Intelligentsia Coffee Wicker Park Coffeebar
1609 W Division StGreat coffee and barely a block away.
Charlatan
1329 West Chicago AvenueOur go-to Italian place in the neighborhood!
Parachute
3500 N Elston AveOur favorite new restaurant in Chicago!
Arts & Culture
If you like art, this is a must. Consistently rated one of the best art museums in the world, the Art Institute has famous works that are recognizable to all, including the Nighthawk and American Gothic, and the works of Van Gogh, Monet, and Picasso
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The Art Institute of Chicago
111 S Michigan AveIf you like art, this is a must. Consistently rated one of the best art museums in the world, the Art Institute has famous works that are recognizable to all, including the Nighthawk and American Gothic, and the works of Van Gogh, Monet, and Picasso
Take a break from the Mag Mile to enjoy some creative pieces at the MOCA.
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Listasafn samtíma í Chicago
220 E Chicago AveTake a break from the Mag Mile to enjoy some creative pieces at the MOCA.
If you're willing to shell out some cash, the Lyric Opera has some of the best Opera out there.
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Lyriska óperan í Chicago
20 N Upper Wacker DrIf you're willing to shell out some cash, the Lyric Opera has some of the best Opera out there.
Great local gallery. You can buy screen-prints from local artists at very affordable prices.
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Galerie F
211 N Milwaukee AveGreat local gallery. You can buy screen-prints from local artists at very affordable prices.
Sightseeing
Start the 2.7-mile trail at Marshfield and Bloomingdale and experience a different side of the city's outdoors that's not on the Lakefront. The trail will take you from Bucktown, through Wicker Park to Humboldt Park. Enjoy it on a bike, with some skates, or on your own two feet with a furry friend.
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Bloomingdale Trail
Bloomingdale TrailStart the 2.7-mile trail at Marshfield and Bloomingdale and experience a different side of the city's outdoors that's not on the Lakefront. The trail will take you from Bucktown, through Wicker Park to Humboldt Park. Enjoy it on a bike, with some skates, or on your own two feet with a furry friend.
Skýjagat
201 E Randolph StA Chicago staple. Take some wonky selfies under the "Cloud Gate"
Any of the Chicago architecture boat tours are great. You see the city from a unique perspective and learn a lot while at it. Don't forget the sunscreen!
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First Lady Architecture Tour
112 E Wacker DrAny of the Chicago architecture boat tours are great. You see the city from a unique perspective and learn a lot while at it. Don't forget the sunscreen!
Getting Around
Divvy
Parks & Nature
This place is a favorite spot of mine. You see the city from a different angle, and it's never crowded. Northerly Island used to be a private airport until Mayor Daley demolished it in the middle of the night around 15 years ago.
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Northerly Island
This place is a favorite spot of mine. You see the city from a different angle, and it's never crowded. Northerly Island used to be a private airport until Mayor Daley demolished it in the middle of the night around 15 years ago.
The most amazing dog park/beach on the planet (from the prespective of a dog-owner)
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Montrose Beach
The most amazing dog park/beach on the planet (from the prespective of a dog-owner)
Must-see place in warm months of the year. Highly recommended!
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Chicago Botanic Garden
1000 Lake Cook RdMust-see place in warm months of the year. Highly recommended!
Entertainment & Activities
Chicago is a comedy city! Don't leave here without seeing a comedy show! This place is not nearly as touristy as Second City, which is also hilarious. But The Neo-Futurists have some amazing comedy for decent prices.
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Neo-Futurists
5153 North Ashland AvenueChicago is a comedy city! Don't leave here without seeing a comedy show! This place is not nearly as touristy as Second City, which is also hilarious. But The Neo-Futurists have some amazing comedy for decent prices.
Drinks & Nightlife
Lost Lake
3154 W Diversey AveAwesome tiki bar, but it can get pretty packed.
A great bar, but come on Wednesday for the Speakeasy night, where you're greeted with anything from live jazz to Flamenco to a Cabaret show.
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Bordel
1721 W Division StA great bar, but come on Wednesday for the Speakeasy night, where you're greeted with anything from live jazz to Flamenco to a Cabaret show.
A relatively new rooftop bar on top of the renovated Chicago Athletic Association Hotel, Cindy's offers excellent brunch during the day and wonderful drinks at night. Well worth it for the view alone.
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Cindy's
12 S Michigan AveA relatively new rooftop bar on top of the renovated Chicago Athletic Association Hotel, Cindy's offers excellent brunch during the day and wonderful drinks at night. Well worth it for the view alone.