Loop
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.
9am: Take a scenic boat ride, Vince Vaughn-style
As Vince Vaughn taught us in The Break-Up, there are many ways to see Chicago. But seeing Chicago by boat with a Chicago River and/or Lake Michigan cruise? You ain’t done Chicago ‘til you’ve done this, kid. Just resist the temptation to jump in the water, unless you’d like a free police escort to boat jail.
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.
Humboldt Park
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.
1:30pm: Walk the 606
It may not quite be NYC’s High Line, but the recently-opened 606 Trail is easily the coolest thing to open in Chicago in quite some time. Take full advantage of the four months of the year when the weather isn’t soul-sucking by exploring this 2.7-mile outdoor recreation path traversing through several hoods from Bucktown to Humboldt Park.
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.
Bridgeport
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.
2pm: Grab some of the finest baseball food in the world
With the two best teams in the game, baseball is king in Chicago. And while the Cubs hog the lion’s share of the glory, the Sox keep making the South Side proud along with some of the finest stadium food on the planet. Batting helmets full of barbacoa-topped nachos? Yes, please.
Edgewater
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.
4pm: Commence maximum beach relaxation at Foster Avenue Beach
As you probably could have guessed by the above entry, the best beaches are found up north. And with wide open spaces and plenty of room for unfurling the blanket while opening a book in peace, Foster Avenue Beach is the best of the best.
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.
River North
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.
5pm: Navigate the underground pedway
Save the architecture tour and trip to the Willis Tower skydeck for when your parents are in town. Real Chicagoans walk the underground pedway, a mysterious and maze like system of underground tunnels that will have you beating the traffic… as long as you know where the hell you’re going.
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.
Wrigleyville
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.
7pm: Watch MLB’s number one team demolish the competition at a Cubs game
Obvious choice? Maybe. But there’s a reason you braved the crowds -- to catch a game at one of the world’s finest ballparks. It also the helps that the Cubs are the best team in baseball. Oh yes, this is the year. Believe it.
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.
Pilsen
6pm: Explore one of Chicago’s finest art scenes on foot
Not only is Pilsen overrun with some of coolest and most colorful murals in the country, it is also a burgeoning arts center that you can explore by foot whenever the hell you want. Or, if you’re into organization, stop by on the first Friday of the month to tour open studios and galleries around the hood.
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.
Andersonville
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.
Wicker Park
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.