Chicago Spring Break Staycation


Mexican Museum of Art

Day One of your Chicago Spring Break Staycation will take you to Pilsen on the city’s near South Side. First stop: The National Museum of Mexican Art, one of Chicago’s best, yet most under-appreciated art galleries. Rotating exhibitions often display works from famous Mexican artists, such as Los Tres Grandes (The Three “Big Ones”), Diego Rivera, José Clemente Orozco, and David Alfaro Siqueiros. Be sure to check out the Rastros y Cronicas gallery, which displays several mixed-media pieces, including woven tapestries, sculptures made from beer glasses, and handmade crafts.

Location: 1852 W. 19th Street
Phone: 312.738.1503
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After you’ve ingested your daily dose of culture, it’s time to head to Simone’s for a few beers and delicious eats. A short ways east toward Pilsen’s Arts District, Simone’s is a swanky bar built from reclaimed pin ball machines and a bowling alley. Their menu is composed of high end bar food and a few Hispanic influenced items with the expected chef inspired liberties. Perhaps our favorite part about Simone’s is the respectable local craft beer list. Don’t get too crazy tonight, though. This staycation is a marathon, not a sprint.

Location: 960 W. 18th St.
Phone: (312) 666-8601
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Three Floyds Brewing Co.

Today we’re getting you out of the city and into some trouble. Well, if you’re into excellent local craft beer, that is. Jump in the car with some friends (of course, a DD is a must for today), and head to nearby Munster, Indiana for a day of drinking at Three Floyds Brewery. Take the $1 per person tour of the brewery, and then settle in at the brewpub and get ready to sample. Alpha King, Robert the Bruce, Gumballhead, Pride & Joy, Topless Wytch… you’ve got a lot of drinking to do. Don’t neglect their rather good pub food, either. You’ll need it to keep going.

If your staycation happens to fall in the end of April, make a point to get there for Dark Lord Day on Saturday, April 30th. It’s every bit as awesome as it sounds.

Location: 9750 Indiana Parkway, Munster, IN
Phone: 219.922.4425
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Already been? Check out one of the city’s other awesome local breweries.

The Hideout

On the assumption you enjoyed Three Floyds to the fullest, we’re going to give most of you a pass, and say get yourself home for some much needed rest. For those of you still ready to rock, though, make your way back to the city and head to the Hideout, arguably the city’s best spot for underground local music. Host to the truly talented musicians of the city, as well as touring bands, this spot is a great follow-up to your local brewfest at Three Floyds. Have a couple (more) beers, tap your foot to whoever’s on stage that night, and be thankful you live in Chicago.

Location: 1354 West Wabansia
Phone: 773-227-4433
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Brunch at The Bongo Room

You had a good day yesterday. It’s time to reward yourself with a scrumptious and filling brunch at Wicker Park’s Bongo Room. Open only for brunch and lunch, this spot always has a wait — consider yourself warned. But trust us when we say it’s worth it. Inventive specials are always available, along with spruced up originals like banana oreo pancakes and a tomatillo salsa scramble. YUM. Eat up, you’ve got lots of shopping to do today!

Location: 1470 N. Milwaukee
Phone: 773.489.0690
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Shopping in Bucktown & Wicker Park

Michigan Avenue is for the tourists… or the very, very brave. We say skip the crowds, and head for the fashionista’s playground known as Bucktown and Wicker Park. Luckily, we’ve strategically placed you right in the thick of it all with your pre-shopping brunch at Bongo Room. Explore boutiques such as Akira, Pitaya, Michelle Tan, Francesca’s, and more.

Not into heels and earrings? Stop by Reckless Records to get your music fix then head to Myopic Books to peruse three floors of used books.

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Second City Comedy

You’ve had a long day. But it’s not over yet! It’s time for some laughs. You may have been to see a Second City sketch comedy show, but we’ve got a little insider’s tip for you. After the last sketch show each night, the cast does a FREE 30-minute improv set, guaranteed to give you a killer ab workout. Head to the Second City for a hilarious nightcap that won’t hurt the wallet. Because you have been shopping all day, after all.

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Bookstore Hopping in Hyde Park

Day four. You aren’t worn out yet, are you? Today we’re taking you to the South Side of the city for a little intellectual stimulation, followed by total relaxation. First stop? The unique and inspiring bookstores of Hyde Park. Head to 57th street, where you’ll find a row of intriguing bookstores waiting to be explored. If you’re like most of us here at, you could spend hours perusing these labyrinths, and we won’t try to stop you. Just be sure to get out of there while it’s still daylight. You won’t want to miss your next stop.

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Promontory Point Park

Perhaps the city’s most enchanting feature, Promontory Point Park exists as a place where Chicago can be picked up, turned around, flipped upside down and seen all over again with new eyes. Four tiers of limestone and boulder create a prehistoric staircase leading to a promenade that provides a completely unique view of the downtown skyline. The adjoining park makes a great place for a picnic, with sprawling green grass and large trees offering shade. Our recommendation? Grab a sandwich after your bookstore jaunt, and cuddle up with a blanket and one of your new books in the park and enjoy a tasty late lunch.

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You’ve spent a day in Pilsen absorbing Mexican culture. You’ve explored Hyde Park on the South Side, and shopped your way through Wicker Park and Bucktown. You’ve even headed to the mysterious land of Indiana for some great beer. Today, you’re heading to Logan Square, one of our favorite Chicago neighborhoods.

Catch a late afternoon movie at Logan Theater, one of the city’s oldest movie theaters still around. Warning: this is NOT your fancy schmancy IMAX movie experience. This an old school spot with kickass popcorn and $4 movie tickets. Don’t expect first-class quality seating — but also don’t expect to pay $6.95 for a pack of Starburst. Embrace the vintage charm, and enjoy a cheap flick. You’re likely to catch a film that’s been in theaters for a while, so if you never got a chance to see The Social Network, there’s still hope. Don’t fill up on popcorn and gummy bears, though. Dinner awaits.

Location: 2646 N. Milwaukee Ave
Phone: 773.252.0627
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Lula Café

One of the leaders in Chicago’s slow food scene, Lula Café serves up some of the city’s freshest menu items in an eclectic atmosphere. The “new american” cuisine focuses on sustainability and eating local, offering a changing menu to go with what’s available that day. The spot proves that mindful dining doesn’t mean boring, and is sure to surprise you with their skillful cooking and exceptional cocktails.

Location: 2537 N. Kedzie Blvd.
Phone: 773.489.9554
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Logan Square Bar Crawl

After a fabulous dinner, what else is there to do than pop in and out of the neighborhood’s many watering holes? By the time you’ve emerged from Lula Café it’s not likely that you’ll be pursuing an entire neighborhood crawl. (You may be literally crawling if you attempt that…) But be sure to stick your head in a few of Logan Square’s bars. We recommend a stop at Longman & Eagle, the Whistler, and the Whirlaway Lounge, where you can end your night with a game of Apples to Apples or Connect Four. Might as well go all out, this is the last night of your staycation. Tomorrow it’s back to alarm clocks and responsibility. So, have fun!

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Got any recommendations for your favorite Chicago staycation activity? Let us know in the comments below!

About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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