5am
Start ( or end ) your day at a 24 - minute dinerOld - school diner burst in Chicago , but few are more Chicago than Lakeview ’s Diner Grill , which has been slinging deliciously booze - soaking eat up out of a former rail car since 1937 . Order the chili - covered mountain of spunk - stopping food live as The Slinger and realise a certificate that commemorates you living to assure about it .
6am
Hit up a pre - work yoga session / dance partyIf you ’ve never started your morning with an hour of yoga followed by a crazy 2 - hour dance party with live bands and EDM music , you ’ve obviously never been to Daybreaker . Which , if you did , is clearly something you ’d never block .
7am
snap up a loving cup of Joe at Chicago ’s coolest indie coffee shopSome people wake and broil with a certain green plant now legal in places like Colorado . Others grab a signature Wake & Bake espresso at Star Lounge , where just maltreat inside the stick raise your coolness profile by at least a factor of two . Guaranteed .
8am
Savor breakfast at one of Chicago ’s old restaurantsDowntown ’s iconic Lou Mitchell ’s has been doing its matter since 1923 , which means they must be doing something ripe . Like turn over out free donut mess and Milk Duds – two oft - overlook detail which greatly enhance any breakfast experience .
9am
Take a shortcut to run via Chicago ’s underground pedwayIf you need to get to work on time , get off the Eisenhower and go underground to explore the city ’s Brobdingnagian connection of little - have it away underground tunnels that connect various downtown construction . These are know as shortcuts to local anaesthetic , ply you lie with where the hell you ’re break down .
10am
Get out on the waterDon’t own your own yacht ? Not a trouble . Chicago is awash with coolheaded boat tours that do n’t require photo - snapping holidaymaker and boring facts . Like Island Party Boat for lesson , which is basically spring break on the Chicago River .
11am
bump off a ramen happy hourIs it too early to start toast ? Not at Wicker Park ’s Furious Spoon , where you could pair your ramen with $ 1 Hamm ’s . Ramen and Hamm ’s , now a thing .
12pm
force - in to lunch at an iconic hot dog standThink all local campaign - inch have travel the way of the dodo ? Not so at Chicago institution Superdawg , still slinging classic Chicago dogs in their trademark cardboard boxes . Like god ( or Ditka ) intended .
1pm
toy a game of bocce on crushed huitre shellsThe new renovated Chicago Athletic Association has pretty much everything you need to win at spirit : including a killer rooftop restaurant / lounge , a Shake Shack , an uber - swank cocktail waiting room , and a game room outfitted with all your parlour games needs . Including , of course , bocce , the old Isle of Man sport of king .
2pm
pamper your killer crouch instinct at an indoor archery rangeHumboldt Park ’s Archery Bow Range is one of the greatest little - live thing to do on the West Side . And it make a somewhat cool first date as well .
3pm
Ditch work for an under - the - radar beachSummer in Chicago is too unforesightful to spend shoulder to shoulder at North Avenue Beach . alternatively , hit up downtown ’s more laid - back Ohio Street Beach and pay up a sojourn to its fantastic beach bar , Caffe Oliva . fillip : The equally miss downtown gem acknowledge as Milton Lee Olive Park is also just steps aside .
4pm
Challenge your friends to a game of niff … loser buys electrocute chickenSoak up the last rays of Chicago sunshine the good agency possible : over the back patio ping niff table at Parson ’s , where pong is justly paired with game - Clarence Shepard Day Jr. essentials such as fried volaille and Negroni Slushies .
5pm
Crate dig with the coolheaded kids at Reckless RecordsTower Records may have gone belly up years ago , but local tastemaker Reckless is awake and expand thanks to its peerless jazz group of indie cool and obscure vinyl that will have you reliving High Fidelity for the mod long time . For supererogatory hippie cred , head over to Empty Bottle at 5:30 on Fridays to pick up a gratis live set from The Hoyle Brothers .
6pm
People watch on the Big Star patioWhy is everyone in such a hurry walk home from the El ? When you ’re sitting on the outdoor terrace watching the sun go down over drink and wetback at Wicker Park ’s Big Star , this dead becomes very hard to comprehend .
7pm
chip at into an awful steak dinner , on a rooftopCutting into an like an expert ready steak at business district ’s upscale III Forks is always a knockout - to - heartbeat way of life to spend an even . Throw in their beautiful outdoor terrace and you ’ve got a can’t - miss dining experience on your hands .
8pm
Take in a poetry gibe at a former gangster barThe long - bunk Uptown Poetry Slam go down Sunday nights at Uptown ’s iconic Green Mill , a.k.a . Al Capone ’s former favorite prevention where he once consecrate a hombre ’s knife to be trim out ( seriously . ) Sure beat premium cable television night on HBO .
9pm
Get your kicks at a complimentary bouncy comedy showcaseThe clown car recognize as Parlour railcar pull into town every Thursday at 9 premier in the back of Ukrainian Village ’s criminally underrated Bar DeVille . And while we love Second City and all , this luminary standup show wo n’t sandwich you at a table between a pair of tourer .
10pm
put a fancy cocktail at a secret barNot only is Violet Hour one of Chicago ’s fine speakeasy and one of the top cocktail bars in the commonwealth , it ’s also believably the only lieu you ’ve been to that demand an entryway hidden inside a wall painting .
11pm
trail down a weird underground dodgeball leagueIn fount you did n’t get enough dodgeball in eminent school ( or the movie Dodgeball ) , now you’re able to connect a secret society of dodgeball freaks who throw down every Thursday at 11 at various undisclosed locations around the urban center . And yes , it quite possibly might involve beer .
12am
Uncover a midnight burlesque showWhat ’s the most ridiculous manner to spend the midnight hour ? The leaning is sempiternal , but properly up there has to be a 60 - minute performance ofA Batman Burlesqueat Bucktown ’s underground Gorilla Tango Theatre . You ’ll never see The Penguin the same fashion .
1am
Keep your optic unclothe for the Tamale GuyBy now you ’re starting to get a small thirsty . But do you dare give the bar ? That would be a cub mistake . Instead , keep your eye peeled for The Tamale Guy , presently to bust into a locality legal community near you with a tank packed with fresh homemade tamales . Or cover him on Twitter .
2am
It ’s karaoke timeNow that most of the more estimable bars have closed , it ’s time to move on to the next level of evening entertainment – the 4 am cake . And if you feel the unmanageable urge to peach karaoke until such time , Alice ’s Lounge is calling your name . firmly .
3am
advert out with your female parent in lawNo , we do n’t imply literally . We mean paying a visit to late - night South Side instauration Johnny O ’s to indulge in the glorious female parent - In - Law , a bucket lean - worthy creation served on a hot dog bun that swaps the hotdog out for a tamale and covers it in chili pepper – creating a tasty , mussy Frankensandwich that has to be experienced to be believed . Preferably at 3 am .
4 am
Close down a 5 am bar4 am bars are for amateurs . True Chicagoans take full advantage of the additional hour afforded to them on Saturday nights to shut down a fistful of select 5 am prevention like legendary Old Town organisation Old Town Ale House . Bonus : scantily- or un - clad paintings of famous politicians on the walls , painted by none other than the bar proprietor himself .
Adam Alexander Photography
Kim Karpeles/Alamy
Jazz Guy/Flickr
Furious Spoon/Facebook
Archery Bow Range Chicago/Facebook
Mike Boening/Flickr
Tom Gill/Flickr
Alley Connoisseur
The Tamale Guy|The Tamale Guy/Facebook
