Chicago

iStock International
Most major Chicago attractions are centrally located, making it easy to pack a variety of activities into a whirlwind weekend without running yourself ragged. Chicago's biggest attractions include the downtown area's many museums, parks, and sky-high observation decks.

Things to do in Chicago

Architectural River Cruise

The city's "living museum" of architectural treasures is candidly and humorously uncovered during these lively boat cruises down the Chicago River. Led by certified docents of the Chicago Architecture Foundation, the 90-minute tours cover more than 50 significant structures, including the Tribune Tower, Leo Burnett Building, Chicago Mercantile Exchange, and Montgomery Ward Company Complex.

224 S. Michigan Ave., IL, 312-922-3432, www.architecture.org
Tags: editor pick | things to do | architecture | history | tour

Art Institute of Chicago

This prestigious museum includes over 500,000 works in its permanent collection. Among the Monets, O'Keefes and Warhols are Grant Wood's American Gothic and Edward Hopper's Nighthawks. A new 264,000-square-foot, Renzo Piano-designed Modern Wing, devoted solely to 20th and 21st century paintings, sculptures, architecture, and photography opened in May 2009, making the museum the second largest in the U.S.

111 S. Michigan Ave., IL, 312-443-3600, www.artic.edu
Tags: family | art | things to do | culture | museum

Center on Halsted

The first LEED-certified gay and lesbian community center in the US offers plenty of resources for the LGBT community – but all are welcome to shoot hoops in the Billie Jean King Recreation Hall, take in a play (or Sunday worship service) at the Hoover-Leppen Theater, or just admire the jaw-dropping skyline views from the rooftop garden.

3656 N. Halsted St, IL, 773-472-6469, www.centeronhalsted.org
Tags: things to do | culture | architecture | gay | sports

Green City Market

Chicago takes a stab at local, sustainable agriculture with this bi-weekly farmer’s market (Wednesday and Saturday, 7am-1:30pm) where an impressive array of area vendors vaunt their finest produce while super chefs and foodies hobnob with the masses. Populist authors like Eric Schlosser (Fast Food Nation) occasionally pop in for a lecture.

Lincoln Park at Clark St. and Stockton Dr., IL, www.chicagogreencitymarket.org
Tags: things to do | culinary | market

Lincoln Park

This 1,200+ acre park hugs the eastern shoreline providing miles of bike trails, beaches, baseball diamonds and ample skyline sightings.

IL, www.chicagoparkdistrict.com
Tags: beach | family | things to do | park

Millennium Park

Da Mayor’s much-hyped vanity project has paid off in spades. Take in a free concert at Pritzker Pavilion, splash around in Crown Fountain, or marvel at Cloud Gate, aka “the Bean.”

Michigan Ave. and Randolph St., IL, www.millenniumpark.org
Tags: family | great value | things to do | park

Museum of Contemporary Art

Everybody admires the MCA’s serious commitment to cutting-edge art – including works by the likes of Lee Bontecou, Dan Flavin, and Jasper Johns. But just try and stop the hipsters from schmoozing and boozing at the insanely popular First Fridays, or working up a sweat while winning fabulous prizes during Bingo/Tango on the second Tuesday of the month.

220 E. Chicago Ave., IL, 312-280-2660, www.mcachicago.org
Tags: editor pick | art | things to do | culture | museum

Pizza Tours

No visit to Chicago is complete without sampling a thick, buttery slice of deep-dish pizza. Launched April 2010, Second City Pizza Tours' two and a half-hour trips visit Chicago's five most famous pizzerias (Gino's East, Giordano's, Uno, Quartino, and Castel Gandolfo). At every location, you'll sample a new pie style (stuffed, deep-dish, brick oven, and thin crust), each ready when your group arrives. Stops take about a 30 minutes and offer a healthy serving of architectural history in between. Admission is $36 for adults, $28 for children. Tours operate from April -- November, every Friday, Saturday, and Sunday at 11:30 a.m.

500 North Michigan Ave. #300, IL, 773-242-0084, www.secondcitypizzatours.com
Tags: food and wine | things to do | tour | pizza | walking tour

Second City

Chicago’s famed temple of improv still cranks out satire and superstars. Steve Carrell, Stephen Colbert, and Tina Fey all cut their teeth here in recent years.

1616 North Wells St., IL, 312-337-3992, www.secondcity.com
Tags: things to do | culture | comedy

Shedd Aquarium

The largest aquarium in the world recreates the eco-system of the Great Lakes and dazzles with a living coral reef, but it’s whale- and dolphin-watching in the Oceanarium that brings in the crowds.

1200 S. Lake Shore Dr., IL, 312-939-2438, www.sheddaquarium.org
Tags: family | things to do | wildlife | aquarium

Steppenwolf Theatre Company

Located outside the city’s main downtown theater district, the renowned Steppenwolf Theatre Company – whose founding members include John Malkovich and Gary Sinise – has featured souch recent draws as Edward Albee’s Who’s Afraid of Virginia Woolf, starring Tony-nominated Amy Morton and Pulitzer- and Tony-winning playwright Tracy Letts. Although ticket prices vary, many weekday and matinee performances cost less than $50. 

1650 N. Halsted St., Illinois, 312-335-1650, www.steppenwolf.org
Tags: things to do | performing arts

The Green Mill

Al Capone is among the legendary patrons to have climbed into one of the giant curvy booths at this legendary jazz joint and speakeasy.

4802 N. Broadway, IL, 773-878-5552
Tags: nightlife | editor pick | historic | great value | things to do | jazz

The Magnificent Mile

Although most famous for its retail offerings, the so-called Magnificent Mile mixes splashy shops like Niketown, American Girl Place, and the Apple Store with architectural landmarks like the Tribune Tower, a 40-story neo-gothic skyscraper speckled with pieces of the pyramids at Cairo; Westminster Abbey; and other famed sites representing all 50 states and dozens of nations. Conclude the shopping trail at Water Tower Place, a vertical mall with more than 100 stores and striking glass elevators. Or, explore the Historic Water Tower building, located one block south of the mall on Michigan Avenue; the limestone, castle-like structure is one of the few to survive the Great Chicago Fire of 1871, and admission is free.

North Michigan Avenue, from the Chicago River to Lakeshore Drive, IL, www.themagnificentmile.com
Tags: shopping | things to do | architecture

Wrigley Field

The Chicago Cubs may never win the World Series, but spending an afternoon swilling beer in the bleachers at this ivy-covered neighborhood ballpark should be a compulsory part of every visitor’s experience.

1060 W. Addison St., IL, www.cubs.mlb.com
Tags: family | smart splurge | things to do | spectator sport

Compare Rates to Chicago






Lisa_hubner

“Book a suite hotel or condo with kitchen when visiting Disney World in Orlando and save big when cooking your own meals.”

Lisa Hubner Travel Deal Expert

Sign up for the Top 25 Newsletter
to get exclusive weekly deals