What Not to Do in Chicago

Ditch that guidebook for our much cooler guide to Chicago—we'll tell you what to really do, and what not to do, in the Windy City. (Spoiler alert: ditch Willis Tower, the Navy Piers, and er, ketchup).

By Molly Fergus

November 11, 2014

Skydeck Chicago at Willis Tower
DON’T: Go to the Willis Tower
You'll wait in a long line and pay $19 to go to the top of what is now the country's second-tallest building. Save the money.
INSTEAD: Have a cocktail at the Signature Room
Settling in at the John Hancock building's 95th-floor bar costs nothing except the price of your cocktail (around $15). Snag a table next to one of the floor-to-ceiling windows, if it's not too crowded, and you'll have a view of four states: Illinois, Wisconsin, Indiana, and Michigan. Ladies, don't skip a visit to the restroom—the views are among the best in the house.

Alamy/Kevin McGill
**DON’T GO TO THE WILLIS TOWER. **You'll pay $18 to wait in line to go to the top of what is now the country's second-tallest building. Save the money.
**INSTEAD: Have a cocktail at the Signature Room. **Settling in at the John Hancock building's 95th-floor bar costs nothing except the price of your cocktail (around $15). Snag a table next to one of the floor-to-ceiling windows, if it's not too crowded, and spy four states: Illinois, Wisconsin, Indiana, and Michigan. Ladies, don't skip a visit to the restroom. The views are among the best in the house.
DON’T: Put ketchup on your hot dog.
This is serious business in Chicago, so much so that Gene and Jude's, a popular hot dog stand, famously refuses to stock ketchup. (The McDonald's next door has started selling packets of the stuff to desperate, ketchup-loving chumps.)

INSTEAD: Eat one of the city's namesake dogs.
This is what you put on a Chicago hot dog instead of ketchup: mustard, relish, a dill pickle spear, tomatoes, chopped white onion, celery salt, and sport peppers.
Alamy/ foodfolio
**DON’T PUT KETCHUP ON YOUR HOT DOG. **This is serious business in Chicago. So much so that Gene and Jude's, a popular hot dog stand, famously refuses to stock ketchup. (The McDonald's next store has started selling packets of the stuff to desperate, ketchup-loving chumps).
** **
**INSTEAD: **Drag it through the garden. This is what you put on a Chicago hot dog instead of ketchup: mustard, relish, dill pickle spear, tomatoes, chopped white onion, celery salt, and sport peppers.

DON’T: Eat only deep-dish pizza.
Chicago's most famous foodstuff—thick-crust, meaty, and cheese-dense deep-dish pizza—is good, yes, but it shouldn't be the only type of pie you try in the Windy City.
Courtesy Dante's Pizzeria
INSTEAD: Sample thin crust, too.
Mom-and-pop pizzerias all over the city serve delicious thin crust—this is the stuff Chicagoans actually eat when they order a pizza. A regional quirk: These pies are cut into small, checkerboard squares instead of floppy slices. The technique leaves plenty of crust-free middle pieces, and a few crunchy, bite-sized triangles on the edges.

© Felix Choo / Alamy
DON’T: Fill up on pizza and hot dogs.
Once you've tried the Chicago dog and the deep-dish pie, it's time to move on; there are plenty of other delicacies to sample in the city.
Alamy/ZUMA Press, Inc.
INSTEAD: Explore the city’s chef scene.
Save some stomach space for the city's serious culinary scene—whether that means sampling Stephanie Izard's small plates at Girl and the Goat or nabbing tickets to Grant Achatz's Next.

DON’T: Visit when it's cold.
Yes, the winters are as bad as you've heard. And no, it's not just because of the wind—Chicago also gets plenty of snow, and bitter Midwestern deep freezes.
Alamy/Chuck Eckert
INSTEAD: Visit in the summer.
Locals embrace the warm weather with the kind of enthusiasm you can only have after surviving months of sub-freezing temps. That means every weekend is packed with festivals (big ones, like Lollapalooza, and smaller, neighborhood-centric fests, too); the beaches are open (yes, you can swim in the lake); and drinking on patios becomes everyone's favorite hobby.

DON’T: Book tickets in the Theater District.
Save the Broadway shows for when you're actually, you know, on Broadway.
Alamy/Kim Karpeles
INSTEAD: See comedy.
The Second City is the most famous of Chicago's improv theaters, and rightfully so: It's churned out the likes of John Belushi, Dan Akroyd, and Tina Fey. But it's not the only comedy venue in town: visit Zanie's for stand-up; iO Chicago for more improv; or the Neo-Futurists for Too Much Light Makes the Baby Go Blind, where actors somehow perform 30 plays in 60 minutes.

Robert Harding World Imagery / Alamy
DON'T: Shop on Michigan Avenue.
The Magnificent Mile isn't all that magnificent in terms of shopping. You'll find mall standbys (H&M, Nordstrom, Gap) and a big Niketown, but that's about it.
Alamy/chicagoview
INSTEAD: Browse in Bucktown and Wicker Park.
These adjoining neighborhoods on the Northwest side have grown up from their hipster roots, and so have the shopping options in both. A mix of indie boutiques, vintage stores, and designer shops make both destinations equally appealing for serious shopping or an afternoon of browsing.

DON’T: Take the family to Navy Pier
Navy Pier is like the Times Square of Chicago: It's iconic, yes, but it's busy and touristy, and there isn't all that much to actually do there.
Alamy/ZUMA Press
INSTEAD: Ride bikes along the lakefront path.
The city has 26 miles of lakefront, which residents take to in droves once those nasty winters finally clear. Grab a Divvy bike (Chicago's bike-sharing program) from one of the docking stations near Grant Park, and pedal south on the path. You'll see Museum Campus, Soldier Field, and Navy Pier—a far better use of your time than lunch at Bubba Gump's.

© Katherine Gaines / Alamy
DON'T: Go to Brookfield Zoo
It's not that Brookfield Zoo is bad, it's just out in the 'burbs. A trip there will eat up an entire day of your vacation.
Alamy/Hemis
INSTEAD: Visit Lincoln Park Zoo.
Though much smaller than Brookfield, Lincoln Park Zoo wins for location and price: Admission is free, and the 35-acre space is situated right along the lake, so you can knock out a beach trip and a zoo visit in one day.

DON’T: Take a double decker bus tour.
They're expensive, they're long, and you can do them in pretty much any city. Plus, Chicago's neighborhoods are easy to explore on foot (provided you pick one or two to see in a day).
Alamy/Chuck Eckert
INSTEAD: Book an Architecture River Cruise.
The best way to see Chicago's rightfully famous architecture is by boat. Book one of the Chicago Architecture Foundation's tours, which cruise down the Chicago River while docents discuss the history of more than 50 of the city's buildings.

What Not to Do in Chicago

DON’T: Go to the Willis Tower

INSTEAD: Have a cocktail at the Signature Room

DON’T: Put ketchup on your hot dog.

INSTEAD: Eat one of the city's namesake dogs.

DON’T: Eat only deep-dish pizza.

INSTEAD: Sample thin crust, too.

DON’T: Fill up on pizza and hot dogs.

INSTEAD: Explore the city’s chef scene.

DON’T: Visit when it's cold.

INSTEAD: Visit in the summer.

DON’T: Book tickets in the Theater District.

INSTEAD: See comedy.

DON'T: Shop on Michigan Avenue.

INSTEAD: Browse in Bucktown and Wicker Park.

DON’T: Take the family to Navy Pier

INSTEAD: Ride bikes along the lakefront path.

DON'T: Go to Brookfield Zoo

INSTEAD: Visit Lincoln Park Zoo.

DON’T: Take a double decker bus tour.

INSTEAD: Book an Architecture River Cruise.