Morning
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Morning

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. View on Map

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. View on Map

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. View on Map

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. View on Map

Afternoon
Will Rice/The 606/Facebook

Afternoon

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

Evening
Bordel Chicago/Facebook

Evening

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

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. View on Map

Big Star
$$ Wicker Park

A lot of things about Wicker Park's Big Star will make you feel like you're in Texas. First, there's the taco-centric menu that features a dozen taco varieties and necessary sides like guacamole and queso....more

Bordel
$$$ Wicker Park

Bordel remains a charming cocktail lounge that stands firmly against the soul-crushing waves of party buses, thanks to the second-story establishment's unmarked door. Once inside, visitors can expect class...more

Black Bull Tapas
Wicker Park

The former Angels & Mariachis space has received a Spanish-style makeover, with tiles imported from Grenada, and metal cage chandeliers overlooking the reclaimed stablewood bar where they're serving up san...more

Happy Village
$ Ukrainian Village

Happy Village is a neighborhood bar located in Ukrainian Village. While it may be unassuming from the outside, the interior is sleek and lively, and there’s a back room housing two ping pong tables. The ba...more

The Boiler Room
$ Logan Square

This industrial restaurant-slash-bar in Logan Square does pizza, beer, and general comfort food (fried cheese balls, poutine, mac & cheese) really really well. The pizza options are staggering: aside from...more

90 Miles Cuban Cafe
$$ Logan Square

There're plenty of reasons to love this easygoing Cuban cafe (with a sibling in Roscoe Village). You'll find tasty Cubano sandwiches and ropa vieja, hearty chicken and skirt steak, and really good seafood...more

East Room
$$ Logan Square

Follow a single red lightbulb to an unmarked door off Milwaukee Ave. in Logan Square, and you’ll eventually find your way into the music venue and speakeasy that is East Room. Though its entry may lead you...more

Located underneath Thalia Hall, Punch House is Pilsen’s underground, 70s-inspired basement pub specializing in… well, punch. With eight options on draft -- including classics like Milk Punch and Pisco Punc...more

Dusek's
$$ Pilsen

Helmed by Longman & Eagle's Jared Wentworth, this Michelin-starred restaurant in Pilsen serves upscale American pub food. Dusek's takes everything you love and makes it better, whether that's cooking Frenc...more

Thalia Hall
$ Pilsen

Thalia Hall is an iconic structure in Pilsen that's been filled with three layers of awesome: a punch-filled cocktail bar in the basement, a beer hall that complements your suds with rustic cuisine on the...more

Rossi's Liquors
$ Near North Side

In a forest green storefront on North State St., with signs advertising fine wines and packaged goods, Rossi's Liquors is a River North mainstay. The store is home to a selection of beers, wines, liquors -...more

Vertigo Sky Lounge
$$ Gold Coast

On the 26th floor of the Dana Hotel, this rooftop lounge is one of the best party spots in the Chicago hotel bar scene. In the winter, Vertigo turns into an indoor/outdoor ice bar where you can do necessar...more

The Dana Hotel
River North

bie invasion this weekend (nice of the zombies to phone ahead). They'll be trying to claw their way inside the fifth floor "Dead Zone", vying for a $1,000 grand costume prize at the undead dance off Friday...more

“Uncle” Lou Mitchell started the family business in 1923, and it's been going ever since. in 1958 they started handing out free donut holes to everyone and boxes of Milk Dudes to the ladies -- they're stil...more

The Gingerman Tavern
$$ Wrigleyville

Unlike its neighboring bars on North Clark St., and despite being located in the shadow cast by Wrigley Field, GMan Tavern is not a sports bar. It’s a cash-only dive with a serious beer selection, a back r...more

Uncommon Ground
$$ Edgewater

Known as one of the "greenest restaurants in America," Uncommon Ground rocks delicious dishes like strawberry-rhubarb pancakes, and blackened catfish with dill sauce. Comforting fare like chorizo-loaded ch...more

Waterfront Café
$$ Edgewater

This super-chill spot is one of the city's best kept secrets. It's great for kicking back with a Cuba Libre and listening to live music. The craft beers and caipirinhas don’t make for a bad afternoon outin...more

Castaways Bar & Grill
$$ Lincoln Park

Located at North Avenue Beach, this bar and grill serves american classics (think burgers and sandwiches) along with a full menu of island worthy umbrella drinks, from daiquiris to margaritas. In addition...more

Hopleaf
$$ Uptown

This Andersonville beer bar is known for its rotating selection of draft beers primarily from the Midwest and Belgium. More than just a bar that serves food, Hopleaf has an outstanding menu of Belgian-insp...more

Hamburger Mary's
Andersonville

When you can’t decide whether you want something salty, sweet, or spicy, why not get all three? Hamburger Mary’s Big Fatty Challenge covers all the basics for when the munchies strike: huge-ass burger, fri...more

Big Joe's
Lincoln Square

So you don’t put ketchup on your Chicago dogs and you’ve jumped into Lake Michigan in polar temperatures, and maybe you even actually enjoy drinking Old Style, but if you’ve never partaken in turtle racing...more

Bridgeport Coffee in Bridgeport is an all-day hangout that has a welcoming, sunny vibe paired with standout roasts like Santa Josefita Bourbon and Sumatra Gayo Sriwijay, plus four rooms of free Wi-Fi. The...more

In continuous operation since 1881, Schaller's Pump is Chicago's oldest bar. A former speakeasy, the Bridgeport tavern changed ownership at the end of Prohibition when George Schaller bought it and changed...more

Skydeck Chicago
$ River North

If you're into breathtaking views from a higher standpoint, Skydeck Chicago at the Willis Tower is the perfect place to try out. And, if you're feeling brave, you can stand on the Ledge, which is basically...more

Howells & Hood is a classic American restaurant offering an extensive list of draft beers on tap along with its menu of soups, salads, pastas, steaks, desserts, and more. Chefs use local and seasonal produ...more

The pH Comedy Theater
$ Andersonville

The pH Comedy Theater has it all: shows, classes, improv, and even a zombie pub crawl. Tickets can be purchased for a reasonable price for any of their musicals or improv shows, and if you're planning a bi...more

Parson's Chicken & Fish in Logan Square knows a thing or two about deep-frying -- the menu features chicken, fish, hush puppies, and cheese curds in all their breaded and battered goodness. Not everything...more

Learn how to shoot with a bow and arrow like a pro at the neighborhood archery emporium. And, if you're a fast learner, you may even wind up at a competition or two.