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  • T T he lakefront is great and downtown houses some of the finest museums in the world, but to really know Chicago is to experience its neighborhoods. To that end, we’ve put together a robust roster of ten mini-itineraries that will immerse you in the best of the city,  no matter the time of day or the company you keep. And we really can’t help you with that last part.
    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

    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. 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

    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. 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

    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. View on Map

    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. 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

    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. 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

    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. View on Map

    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. 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.

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