A weekend’s worth of time will let you take in some of Chicago‘s best sights. Begin your first day in the Windy City at the Willis Tower, arriving before it opens at 10 a.m. to get a jump on the lines to zip up to the observatory.
At 1,353 feet, the observatory offers a view of Michigan, Wisconsin and Indiana when the clouds are at bay.
After seeing Chicago by land, look at it by sea — or rather, river. Hop on a riverboat tour along the Chicago River to see the city’s famous architecture. Grab lunch at River North restaurants Frontera Grill, Topolobampo or Xoco (the most casual of the trio), all from new Mexican cuisine pioneer and Chicagoan Rick Bayless.
After lunch take a walk through the Lincoln Park Zoo, one of the country’s only free zoos. There you can see the usual bears and lions and the not-so-usual snow leopards and sloths.
You’ll have time to kill before seeing a nighttime improv show at the legendary Second City (be sure to purchase tickets in advance because shows consistently sell out). Spend that waiting time wandering through the great nearby neighborhoods of Lincoln Park and Old Town.
Armitage Avenue is an excellent strip for independent boutiques in Lincoln Park. Stop by Art Effect, an eclectic shop that carries everything from clothing to ibride trays to a parking meter alarm. Stop at Adobo Grill, a Mexican eatery near the Second City theater that has delicious guacamole and margaritas.
You’ll want to arrive at Second City to wait in line for a table or even just a chair; seating is first-come, first-served, so early fans of comedy will get the best tables. But don’t jet out once the show is over, the jokesters put on a free improv set after the last performance every night but Friday.
For your second day, plan ahead and get tickets for bleacher seats at Wrigley Field. As you cheer on the Cubs, resist the urge to order a ballpark dog and save your appetite instead for authentic Chicago hot dogs with the works at the Wiener Circle. Be sure to ask nicely; the sassy staff is known to dish out insults with the cheese fries (no doubt its patience was strained long ago by drunken Cubs fans and the area’s weekend revelers).
To see a less-touristy side of the city, travel southwest to Bucktown and Wicker Park. Fashionistas will want to point their Choos in the direction of p.45 to browse racks of clothing from 3.1 Phillip Lim and local designer Lara Miller.
For dinner, try Coast Sushi Bar for some of the city’s best sushi (bring your own booze). Then, head to Hot Chocolate for delicious hot chocolate with housemade marshmallows. The Black and Tan (one part hot fudge, two parts medium hot chocolate) is so rich, it’ll count as dessert.
Try to reserve tickets for a show at the renowned Steppenwolf Theatre or a production from the city’s many storefront troupes (ones to check out: the bold Hypocrites or the rockin’ House of Theatre Chicago).