Guidebook for Chicago
Drinks & Nightlife
Great little bar with patio. Has delicious vegan/vegetarian food and their brunch is great. And it's right across the street from the apartment!
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Handlebar
2311 W North AveGreat little bar with patio. Has delicious vegan/vegetarian food and their brunch is great. And it's right across the street from the apartment!
Pre-Prohibition-era Speakeasy with no sign. It's a pretty cool place to stop in for a very fancy cocktail. Talk to me for an explanation on how to get in.
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The Violet Hour
1520 N Damen AvePre-Prohibition-era Speakeasy with no sign. It's a pretty cool place to stop in for a very fancy cocktail. Talk to me for an explanation on how to get in.
A rooftop bar located at the top of the tallest building in this area has great views and decor with really inventive and creative cocktails.
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The Up Room
2018 W North AveA rooftop bar located at the top of the tallest building in this area has great views and decor with really inventive and creative cocktails.
A great bar on the second floor of the Chicago Athletic Association Hotel. They've got all kinds of games like billiards, foosball, shuffleboard, and bocce. The drinks are good and they've got a few local beers. A fun spot!
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The Gage
24 S Michigan AveA great bar on the second floor of the Chicago Athletic Association Hotel. They've got all kinds of games like billiards, foosball, shuffleboard, and bocce. The drinks are good and they've got a few local beers. A fun spot!
A fun place where you can play full-sized shuffleboard! A rarity in any city. Great bar scene, too.
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The Royal Palms Shuffleboard Club
1750 N Milwaukee AveA fun place where you can play full-sized shuffleboard! A rarity in any city. Great bar scene, too.
Food Scene
Some of the best tacos in the city with one of the best street patios in the city.
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Big Star
1531 N Damen AveSome of the best tacos in the city with one of the best street patios in the city.
Awesome little ramen joint. Get the delicious Furious Ramen with pork, chicken and a poached egg! Open late!
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Furious Spoon Wicker Park
Awesome little ramen joint. Get the delicious Furious Ramen with pork, chicken and a poached egg! Open late!
Awesome late-night pizza spot. They've got a huge unique variety of pizza flavors by the slice along with a lot of vegan options.
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Dimo's Pizza Wicker Park
1615 N Damen AveAwesome late-night pizza spot. They've got a huge unique variety of pizza flavors by the slice along with a lot of vegan options.
Fun New Haven-Style pizza brewpub with award-winning beer brewed onsite!
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Piece Brewery
1927 W North AveFun New Haven-Style pizza brewpub with award-winning beer brewed onsite!
Ipsento Coffee
2035 N Western AveCozy coffee shop with delicious coffee and good food menu.
Bake
2246 W North AveNice little bakery with good hot and iced coffee.
Jay's Beef
2255 W North AvePerfect location to score that classic Chicago Italian Beef Sandwich! The original!
This is the best fried chicken in the city, hands down. A little off the beaten path but worth the trip.
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Honey Butter Fried Chicken
3361 N Elston AveThis is the best fried chicken in the city, hands down. A little off the beaten path but worth the trip.
A local favorite and a unique take on deep dish. The pie has a caramelized crunchy crust and is more bready than the cracker-crust you might get at the more well-known deep dish purveyors. If you can make it to 2 deep dish places on your trip, this is a must get.
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Pequod's Pizza
2207 North Clybourn AvenueA local favorite and a unique take on deep dish. The pie has a caramelized crunchy crust and is more bready than the cracker-crust you might get at the more well-known deep dish purveyors. If you can make it to 2 deep dish places on your trip, this is a must get.
Classic American diner fair but elevated and made very unique! This place doesn't take reservations so if you're trying to find a good spot without a crazy wait in Fulton Market, your best bet is to stop in here and put your name in. Then if the wait is long you can walk around and if you happen to find another restaurant you'd rather try out without a wait, then go for it! But at the very least you've got a really good restaurant to try our in your back pocket.
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Little Goat Diner
3325 W Randolph StClassic American diner fair but elevated and made very unique! This place doesn't take reservations so if you're trying to find a good spot without a crazy wait in Fulton Market, your best bet is to stop in here and put your name in. Then if the wait is long you can walk around and if you happen to find another restaurant you'd rather try out without a wait, then go for it! But at the very least you've got a really good restaurant to try our in your back pocket.
Great burgers extremely close to our apartment. Au Cheval offers perhaps the best burger in the country and they have come up with a more "fast food" version of it and only sell it at their neighborhood locations of Small Cheval. It's worth getting along with their fries and a shake. Oh, and don't forget to get a shot in your shake; my favorites are a shot of whiskey in the chocolate shake or a shot of fernet in the vanilla shake.
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Small Cheval
1732 N Milwaukee AveGreat burgers extremely close to our apartment. Au Cheval offers perhaps the best burger in the country and they have come up with a more "fast food" version of it and only sell it at their neighborhood locations of Small Cheval. It's worth getting along with their fries and a shake. Oh, and don't forget to get a shot in your shake; my favorites are a shot of whiskey in the chocolate shake or a shot of fernet in the vanilla shake.
Sightseeing
Don't pay for a ticket to the Hancock observatory, skip most of the lines and get an expensive drink at The Signature Lounge instead!
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The Signature Room at the 95th®
875 N Michigan AveDon't pay for a ticket to the Hancock observatory, skip most of the lines and get an expensive drink at The Signature Lounge instead!
Willis Tower
233 S Wacker DrAwesome Ledge attraction you can see through and great views
Lincoln Park dýragarður
2001 N Clark StGreat zoo near the lake and it's free!
This is my favorite way to see the city. A great 90min boat tour through a couple branches of the Chicago river gives you a really unique perspective of the city and it's amazing architecture. This one is hosted by a volunteer docent from the Chicago Architectural Foundation so you'll be getting the real scoop on Chicago's buildings and history. They have coffee and alcoholic drinks at the bar, too!
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First Lady Architecture Tour
112 E Wacker DrThis is my favorite way to see the city. A great 90min boat tour through a couple branches of the Chicago river gives you a really unique perspective of the city and it's amazing architecture. This one is hosted by a volunteer docent from the Chicago Architectural Foundation so you'll be getting the real scoop on Chicago's buildings and history. They have coffee and alcoholic drinks at the bar, too!
This bar/restaurant at the top of the Chicago Athletic Association Hotel has one of the best views of Grant Park and Lake Michigan in the city. Head up here for a drink and the view. The food is good but overpriced, unsurprisingly. Don't sleep on the Game Room bar on the second floor of this hotel, as well!
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Cindy's
12 S Michigan AveThis bar/restaurant at the top of the Chicago Athletic Association Hotel has one of the best views of Grant Park and Lake Michigan in the city. Head up here for a drink and the view. The food is good but overpriced, unsurprisingly. Don't sleep on the Game Room bar on the second floor of this hotel, as well!
Chicago's famous sculpture colloquially known as "The Bean." It's worth seeing and won't take you long to experience and take your bean reflection photos. And best of all, it's completely free!
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Skýjagat
201 E Randolph StChicago's famous sculpture colloquially known as "The Bean." It's worth seeing and won't take you long to experience and take your bean reflection photos. And best of all, it's completely free!
Shopping
Water Tower Place
835 Michigan AveHuge mall near the historic Water Tower.
Arts & Culture
This is a fantastic museum in downtown Chicago. The Modern Wing is my personal favorite area but they also have some really historic and famous paintings in their collection throughout the museum.
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The Art Institute of Chicago
111 S Michigan AveThis is a fantastic museum in downtown Chicago. The Modern Wing is my personal favorite area but they also have some really historic and famous paintings in their collection throughout the museum.
Neighborhoods
Logan Square is one of the trendiest neighborhoods in the city. It's a quick Blue Line train ride away, just 2-3 stops. There are tons of bars, restaurants, art galleries and coffee shops.
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Logan Square
Logan Square is one of the trendiest neighborhoods in the city. It's a quick Blue Line train ride away, just 2-3 stops. There are tons of bars, restaurants, art galleries and coffee shops.
Also known as "Restaurant Row" there really isn't a place in this area that I would hesitate to recommend. A good amount of nightlife can be found here but there is absolutely no shortage of great food.
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Fulton Market
Also known as "Restaurant Row" there really isn't a place in this area that I would hesitate to recommend. A good amount of nightlife can be found here but there is absolutely no shortage of great food.