· The Publican: Steak tartare. Schnitzel sweetbreads. Veal brain. The Publican has been at the forefront of the Chicago foodie scene for a couple years now and there's no backing down. They arrange collaborative "beer dinners" with Big Star and they're one of the best places in the city to try bone marrow or oysters if you're a picky eater.
· Big Star: We've been obsessed with Big Star since last spring, and we aren't alone. The spartan, hip spot churns out organic tacos and artisan cocktails and of course the place is consistently packed, including the large patio when the weather is right. Big Star has some big brains behind it, including master chef Paul Kahan, the man behind Blackbird and The Publican.
· Sultan's Market: There's one on Clark and one on North Avenue, but whichever you choose, the Sultan's falafel will fast become your standby Middle Eastern snack. We've been scarfing these things down for over five years and always have to wait in a line.
· Longman & Eagle: New York hipster with a Chicago friendliness (and a Michelin star). Longman & Eagle is a bar, restaurant and hotel (see below) and known for ridiculously addictive meatballs. We love the wild boar sloppy joes and the $8 "PBR Breakfast."
· Next: It's not open now but sure will be when Virgin America begins flights to Chicago in late May. Next is the next restaurant from Alinea's superstar chef Grant Achatz, and already we know we won't be able to get reservations til early fall.
Queso fundido at Big Star
· Violet Hour: If you're talking Chicago with someone who recently visited the city and is trying to remember the name of the place they had some amazing, crafted cocktails, then the chances are high they're thinking of The Violet Hour. Here's the thing, too: it's right around the corner from Big Star and affiliated with both Big Star and The Publican. The winning team just can't lose. Order "The Great Speaker," which mixes Coffee-Pecan Bitters with Tequila.
· Old Town Ale House: If you call it a dive bar, you'll incense the regulars and devotees of true dive bars, but it kinda is one. The drinks are cheap, there are tables to actually sit and chat with your friends, the place is a legend and the walls are covered in raunchy paintings. What more could you want? It's also right on the edge of Old Townone of the most beautiful neighborhoods in Chicago for a good walk.
· Xoco by Rick Bayless: Hot chocolate and housemade churros. 'nuff said.
· Longman & Eagle: It's a hotel! No, it's a bar! No, it's a restaurant! Hell, it's all three and although the hotel element is small, rooms are well done and start at only $75. Bonus points for it being closely located to a Blue Line CTA stop (aka the El to O'Hare).
· theWit: Want to stay downtown? Surego with theWit for its scene-y rooftop bar, excellent screening room and two great restaurants. Normally we wouldn't advise eating at hotel restaurants, but their State & Lake and Cibo Matto are worth it.
· Hotel Palomar: This is the newest Kimpton Hotel in town, which means (for Kimpton inTouch members (free to join)) free WiFi, evening wine receptions in the lobby, morning coffee in the lobby, and little surprises here and there. Not to mention excellent rooms and a location that keeps both the loop and River North in an easy walk.
· The James: So chic it hurts. The James is a master of the Foursquare deal, so stay here or not, you may end up drinking here. If you're feeling fancy, upgrade to a mini-suite and make use of the awesome entertainment corner with projector.
A room at Longman & Eagle
· Bike the Lake Shore Path: We wouldn't recommend it right now because it's still quite cold in the Windy City, but come May when the VX flights begin, the Lake Shore Path will be the place to hang out, or get active. Sand volleyball courts, roller blading, biking, running, tanning, swimming...it all happens here, right on the lake. Plus North Avenue Beach's boat-shaped beach restaurant should be open by then, and it boasts one of the best views in the whole city for the cost of a cheap-ass frozen daiquiri.
· Shop Field Notes & Threadless: Indie businesses can really flourish in Chicago, and two of our favorites are getting so popular we don't think we can rightly call them indie anymore. Field Notes makes some of the best notebooks out there, and if you're in Chicago you're welcome to stop right into their West Loop factory & warehouse to pick up your orders. Threadless, a T-shirt company, used to offer the same service, but now they've got two stores of their very own that offer free totes with each purchase, and the newest tees every Friday. Look 'em up.
· Go Fly a Kite on Northerly Island: Or tan, or swim or jog or just take a walk on this former airport that sticks out into Lake Michigan. It'll be gorgeous in May. The old Meigs Field has a beach, giant lawn, jogging/biking route, plenty of big rocks for sitting on and quiet contemplation or sketching, and it's super convenient to the Museum Campus. See our own photo gallery of the place here.
· Snack here and there at a Farmers Market: There's a whole slew to choose from, but the Green City Market is the only year-round one. By May, however, you should be able to head to our favorite: the Lincoln Park Market on the south end of the park every Wednesday and Saturday from 7am to noon.
An aerial view of Northerly Island
[Photo credits, in order: Jaunted, Jaunted, Longman & Eagle, Jaunted]