8 Things to Know Before Visiting Chicago

In this guide

1. 1. The weather changes fast
2. 2. You don’t need a car
3. 3. The Loop is only the start
4. 4. The architecture boat tour is worth it
5. 5. See the Bean early
6. 6. Deep dish isn’t what locals eat every day
7. 7. The lakefront is free and huge
8. 8. A Cubs game is about more than baseball
9. A few quick etiquette notes
10. Budget tips
11. When to go
12. Common questions

Here are eight things I’d want to know before a first visit. Some will save you money, and a couple will save you from being cold and miserable.

1. The weather changes fast

Chicago weather is famously unpredictable. A warm spring morning can turn cold by lunch when the wind shifts off the lake. Summer is hot and humid, and winter is seriously cold, often well below freezing for weeks.

Pack layers whatever the season. Near the lake, it’s usually cooler in summer and windier year-round. And yes, the Windy City nickname is mostly about politics, but the wind is real too.

2. You don’t need a car

Chicago has a great public transit system. The L, the elevated train, connects downtown with both airports and most neighborhoods visitors want to see. Buses fill in the gaps, and you can tap a card or your phone to ride.

Parking downtown is expensive, often $40 a night or more at hotels. Unless you’re taking day trips, skip the rental car. The Blue Line from O’Hare and the Orange Line from Midway are the cheapest way into the city.

3. The Loop is only the start

The Loop is downtown, named after the elevated train tracks that circle it. It’s where you’ll find the big museums, Millennium Park and the famous buildings. But Chicago is really a city of neighborhoods.

Head to Wicker Park for shops and bars, Pilsen for Mexican food and murals, Andersonville for a cozy Swedish-rooted main street, and Hyde Park for the University of Chicago and the Museum of Science and Industry. Each feels like a different town.

4. The architecture boat tour is worth it

I’m usually skeptical of big tourist tours, but the river architecture tour is the one most locals actually recommend. Chicago is where the skyscraper was born, and seeing the buildings from the river is the best way to understand the city.

The 75 to 90 minute tours run from spring through fall. Book ahead on summer weekends, and bring a jacket. It gets breezy on the water, even in July.

5. See the Bean early

Cloud Gate, better known as the Bean, is in Millennium Park and is one of the most photographed things in the city. By midday, it’s surrounded by people. If you want a clean photo, go before 9am.

While you’re there, walk to the Crown Fountain with its giant video faces, then cross the Nichols Bridgeway to the Art Institute of Chicago. It’s one of the best art museums in the country and deserves at least half a day.

6. Deep dish isn’t what locals eat every day

Try deep dish at least once. It’s more like a pie than a pizza, with a thick buttery crust, cheese on the bottom and chunky tomato sauce on top. It takes around 45 minutes to bake, so order ahead or expect to wait.

But here’s the secret: most Chicagoans eat tavern-style pizza more often. It’s thin, crispy and cut into squares. Also try an Italian beef sandwich and a Chicago-style hot dog. Just don’t ask for ketchup.

7. The lakefront is free and huge

Lake Michigan is right there, and it’s one of the best things about the city. The Lakefront Trail runs about 18 miles along the shore, past beaches, parks and harbors. You can walk it, bike it or rent a scooter.

In summer, North Avenue Beach and Oak Street Beach are packed with people swimming and playing volleyball, with the skyline right behind them. It doesn’t cost anything, and it’s the city at its best.

8. A Cubs game is about more than baseball

Wrigley Field opened in 1914 and is the second-oldest ballpark in the majors. Even if you don’t care about baseball, a game here is fun. The ivy-covered walls, the old scoreboard and the rooftop seats across the street make it special.

Tickets for weekday games are usually cheaper. The surrounding Wrigleyville area fills with bars before and after. If you’re there outside the season, there are stadium tours.

A few quick etiquette notes

Stand on the right on escalators and walk on the left. Chicagoans move quickly, especially downtown at rush hour. Don’t call it “Chi-town” if you want locals to take you seriously. And the Willis Tower is still the Sears Tower to plenty of people who grew up here, so don’t be surprised if you hear both names.

For the best city view, skip the line at the Skydeck and go for a drink at a hotel rooftop bar or the Signature Lounge on the 96th floor of the John Hancock building, now called 875 North Michigan. A cocktail costs about the same as a ticket, and the view is just as good.

Budget tips

Chicago is cheaper than New York or San Francisco, but taxes add up. The sales tax is over 10%, and hotel taxes are high, too. Free things help: Lincoln Park Zoo, the Chicago Cultural Center and the lakefront cost nothing. Many museums also have free days for Illinois residents, so check before you book.

When to go

Late spring through early fall is the best time. September is my favorite, with warm days, fewer crowds and lots of festivals. Winter is cold but has its charm, with holiday markets and lower hotel prices.

Common questions

D

DavidMarketer, YouTuber, Traveler

Addicted to traveling. Currently living in Valencia, Spain.

More about Pinlions Travel →