Since 1969, restaurant, hotel, travel & other witty reviews by a handpicked, worldwide team of discerning professionals—and your views, too.

Chicago City Trip

Chicago's impressive skyline rises above the shores of Lake Michigan

72 Hours in Chicago

by Jennifer Olvera


Chicago exudes big personality, from a murky history filled with gun-running gangsters and free-flowing speakeasies to the countless comedians who have launched their careers here. Often dubbed the "Heart of America," the windy city of Chicago is where East Coast speed meets Midwestern manners, and musicians like Muddy Waters, John Lee Hooker and Louis Armstrong pushed the envelope of what we now know of blues and jazz.

Chicago is a thriving metropolis chock-full of forward-thinking food and fashion, tall buildings, bright lights and those bone-chilling winter winds sweeping off Lakeshore Drive. Chicago's dining scene rivals the nation's best destinations, and with a public transit card, ravenous travelers can trek along the banks of Lake Michigan to the culture filled streets of the South Side in no time. Second City? Not if you ask anyone in this town.

The snowy shore of Lake Michican outline the eastern boarder of Chicago

CHICAGO DAY 1: Museum of Contemporary Art, The Art Institute of Chicago and Sears Tower Skydeck

On your first morning in Chicago, make sure to wake up early and hurry over to Brendan Sodikoff's always-bustling Doughnut Vault; when the piping-hot wonders run out, that's it for the day.

From there, head to some of the must-see tourist hubs. The city's rich museum culture promises endless educational opportunities, and a stop at the Museum of Contemporary Art is essential. Lauded for its collection of art of our time — from painting, sculpture and photography to video, performance and film — the museum features many thought-provoking exhibitions; its permanent collection includes works from Franz Kline and Andy Warhol. When weather permits, be sure to check out the terraced garden, which affords great views of Lake Michigan.

The Modern Wing at the Art Institute of Chicago

Of course, the comprehensive collection — particularly the array of Impressionist and American art — at The Art Institute of Chicago, is unparalleled. Originally constructed for the 1893 World's Columbian Exposition, it began as a joint museum and school, and remains one of America's preeminent museums and educational art institutions today. First, make your way to the recently unveiled Renzo Piano-designed, 264,000-square-foot Modern Wing, which houses European works from 1900 to 1950. Depending on how long you hang out, you might want to relax at Tony Mantuano's Terzo Piano, a sedate, stylish spot serving local, organic and sustainably produced Italian fare.

When lunchtime arrives, keep things casual but cool with a stop at The Gage, Irish-born Billy Lawless' pub with upscale grub from Dirk Flanigan, or grahamwich, Graham Elliot's ode to inexpensive hand-helds.

Willis Tower's Skydeck affords views of Chicago and the surrounding area

Next, visit the Willis Tower Skydeck located on the legendary building's 103rd floor. Here you'll delight in the panoramic views of the city's architecture, as well as glimpses of Michigan, Indiana and Wisconsin on a clear day. Should you dare, step onto the enclosed, glass-bottom ledge. Of course, if something more traditional is your thing, a meal at the Signature Room at the 95th in the John Hancock Center will more than suffice.

Afterward, mosey on over to Gibson's Steakhouse for some of the city's finest prime cuts, football-sized lobster tails and über-cold martinis. As if the walls decked with autographed publicity photos didn't clue you in upon your entry, you might want to keep your eyes peeled for the smattering of in-town celebrities, famous tycoons and local athletes who frequent this haunt.

Now that you're on a roll, it's time to take in some of the city's legendary nightlife. Most Chicagoans would tell you blues and jazz are where it's at. Although there are more frequently treaded spots like Buddy Guy's Legends and Green Mill, for our money Kingston Mines is the place to go for a non-stop tune fest. Live music is kicked out on two stages every night, and the cover charge is surprisingly affordable.

Continue to Day 2


Ready to book a trip now?
Get exclusive savings on hotel rooms

Downtown Chicago

* Images by Choose Chicago


Plan a voyage to a tropical paradise aboard one of GAYOT's Best Caribbean Cruises.
Get the 411 on the City of Angels. Find the city's top hotels, restaurants, attractions and more with GAYOT's guide.