8am: Grab breakfast at one of Chicago’s most iconic restaurants, Lou Mitchell’s
Is there a better way to start your day than with a Belgian malted pecan and bacon waffle at this iconic downtown cash-only diner that’s been slinging eats since 1923? No, there is not. That’s just science, people.
11am: Perfect your people-watching skills over lunch at Howells & Hood
Hours at sea makes a man (or woman) hungry and, while there are endless options in the Loop, it’s hard to beat the outdoor patio at Howells & Hood, located smack in the middle of downtown next to Tribune Tower. Anything is good, but the kimchi burger is the stuff of legend.
Noon: Bust out the bow at arrow at Archery Bow Range Chicago
How the hell is it noon already and you haven’t shot a bow and arrow yet? Correct that egregious oversight at this neighborhood archery emporium when you really feel like doing something different.
3pm: Day drink on the patio at Parson’s
After a long day (or long 90 minutes) of strenuous urban hiking (i.e., walking), it’s time to kick back with a Negroni Slushy and fried chicken at Texas-style Parson’s Chicken & Fish.
Noon: Pretend to work at Bridgeport Coffee
This all-day hangout helps anchor a recent neighborhood revival thanks to its welcoming, sunny vibe paired with standout roasts and four rooms of free Wi-Fi. In other words, it’s the perfect place to hole up for hours and (pretend to) get tons of work done.
1pm: Hang with grizzled old timers at Chicago’s oldest bar, Schaller’s Pump
Maria’s Packaged Goods is a worthy neighborhood institution, but when push comes to shove there are fewer places more uniquely Bridgeport than Chicago’s oldest continually running tavern which has been serving drinks (sometimes illicitly) since 1881. Besides a history lesson, grab a great parking spot and walk 15 minutes to The Cell for a Sox game.
3pm: Hit one of Chicago’s best beach bars at the Waterfont Café
Instead of slamming beers with meatheads at North Avenue Beach’s famous Castaway’s, head a bit further north to discover a lakeside oasis of relaxation at this super-chill waterfront café, where you can listen to the ripples of the water as you order up your second (or third) lobster roll.
7pm: Catch underrated underground comedy at pH Theatre
Not only is Edgewater one of Chicago’s most underrated hoods, it also houses one of its most underrated comedy theatres. While no one would fault you for going to Second City, you won’t be awkwardly sandwiched into a table next to a couple from Iowa at this locals-heavy temple of DIY upcoming improv talent.
4pm: Curse the sunlight at old man bar Rossi’s
Belly up to the bar at old man tavern Rossi’s and meet one of the most “interesting” clientele you’ll find downtown. It’s always 5 o’clock there.
7pm: Party on a sexy hotel rooftop at Vertigo Sky Lounge
Do you like DJs and fire pits? Then you’ll love Vertigo Sky Lounge, Chicago’s only year-round indoor/outdoor lounge where the beautiful people go to be seen while sipping cocktails and enjoying panoramic city views 26 floors up at the Dana Hotel.
6pm: Pregame at Gingerman Tavern
Wrigleyville’s frat bro culture ends at the doors of the across-from-Wrigley Gingerman Tavern, one of the few not-terrible bars in the hood.
10pm: Drink the only certified organic beer in Illinois at Uncommon Ground
As one of the “greenest restaurants in the country,” Uncommon Ground is famous for its organic rooftop farm that grows herbs and produce that are used at both its Wrigleyville and Edgewater locations. It also recently opened the state’s first certified organic brewery, Greenstar Brewing.
8pm: Go to Punch House for… punch
After grabbing dinner at the newly Michelin-starred Dusek’s, head downstairs to the neighborhood playpen that is Punch House for some of the best punch-based creations in town, like Space Juice.
9pm: Catch a show at Thalia Hall
Now that you’ve got the juices flowing, do you feel like catching a concert at one of Chicago’s finest indie rock venues that also doubles as a beautifully restored 1892 opera house? Yes, yes you do.
7pm: Dinner at Hopleaf
There are many excellent restaurants in Andersonville. But in this hot cutting-edge hood, you get dinner at an old-school bar. You get dinner at Hopleaf. You get mussels and fries at Hopleaf. Case closed.
8pm: Check out a weird show at Hamburger Mary’s
Drag shows? Hamburgers? Attic parties? Yes, Hamburger Mary’s has all three. You won’t be bored.
11pm: Turtle racing at Big Joe’s
Local dive bar Big Joe’s hosts turtle racing every Friday night as your antidote to the ordinary. Get a raffle ticket to be assigned a turtle, who will then “race” other shell-bearing reptiles across an 8-foot wide track that resembles a cross between a curling rink and ice hockey table. Just remember, there are rules.
9pm: Get dinner on one of Chicago’s finest patios, Big Star
Tacos on the patio at Big Star are a right of passage in Chicago. And if you show up at night instead of crowded sunny day you might actually get a table, as they’re slinging tacos al pastor and mescal shooters on the patio ‘til 2 or 3am.
10pm: Visit a speakeasy above a taco shop at Bordel
Yes, you could just walk across the street from Big Star to Violet Room, one of America’s best cocktail bars/speakeasies. But if you’re in the mood for something different, why not visit a different speakeasy… this one above Black Bull. It’s called Bordel and it slips under the radar with burlesque shows, flamenco dancers, and obligatory sexy red velvet.
1am: Play a game of late-night ping pong at Happy Village
Some people are serious about their ping pong. You can tell, because they bring their own paddles. You can find them (along with plenty of first-timers) in the back of this neighborhood institution.