Top 10 Chicago Travel Tips: Deep Dish Pizza, The Bean, and River Tours
“Chicago is an October sort of city even in spring.”
Chicago is arguably the most American of all American cities. It gave birth to the skyscraper, refined the blues, and invented a pizza so thick you need a knife and fork to eat it. It sits majestically on the shores of Lake Michigan, looking more like an oceanfront city than a lakeside one.
However, Chicago has brutal winters and a "Loop" that can confuse first-time visitors. Here is your essential guide to navigating the Windy City.
1.
The Architecture River Tour is Mandatory
This is not just a boring boat ride; it is widely considered the best tourist attraction in the US.
The Tip: Don't just pick any boat. Book the Chicago Architecture Center River Cruise (aboard Chicago’s First Lady). The guides are certified docents who tell incredible stories about how the skyscrapers were built. It’s the best way to see the city.
2.
Deep Dish Pizza Takes 45 Minutes
Chicago-style pizza is not a snack; it’s a casserole.
The Rule: Whether you choose Lou Malnati’s (buttery crust) or Giordano’s (stuffed), be prepared to wait. It takes at least 45 minutes to bake.
The Hack: Order your pizza as soon as you sit down (or while you are waiting for a table), then order appetizers and drinks.
3.
Visit "The Bean" at Sunrise
Cloud Gate (affectionately known as "The Bean") is the city's most famous photo spot.
The Hack: If you go at 2:00 PM, it will be covered in fingerprints and surrounded by thousands of tourists. Arrive at 7:00 AM. You will have the reflection of the skyline all to yourself for that perfect Instagram shot.
4.
Skydeck (Willis Tower) vs. 360 Chicago
Everyone wants to see the view from the top, but which tower is better?
The Tip: The Willis Tower (formerly Sears Tower) is higher and has "The Ledge" (glass box). However, 360 Chicago (John Hancock Center) offers better views of the lake and the beach. Plus, it has "TILT," a moving glass platform. Both are great, but the line at 360 Chicago is often shorter.
5.
Take the "L" Train from the Airport
Taxis and Ubers from O'Hare Airport can cost $50-$80 and get stuck in terrible traffic.
The Hack: Take the Blue Line (L Train) directly from O'Hare to downtown (The Loop). It costs only $5 and takes about 45 minutes. It runs 24/7 and is the most authentic Chicago experience.
6.
The Garrett Popcorn Mix
You will smell the caramel aroma blocks away.
The Rule: You must order the "Garrett Mix" (formerly Chicago Mix). It is a blend of CaramelCrisp and CheeseCorn. It sounds weird to mix sweet caramel and salty cheese, but it is addictive. It’s the ultimate Chicago souvenir.
7.
Walk the Lakefront Trail
Chicago has 18 miles of paved path right next to the water.
The Tip: Rent a Divvy Bike (the city’s bike-share system). Ride from Navy Pier south to the Museum Campus for the best skyline views, or north to North Avenue Beach to watch the volleyball players. It’s safe, flat, and beautiful.
8.
Navy Pier is a Tourist Trap (Mostly)
Locals generally avoid Navy Pier unless there are fireworks.
The Warning: It is full of overpriced chain restaurants and souvenir shops.
The Hack: Walk the pier for the views and maybe ride the Centennial Wheel, but do not eat there. Walk 15 minutes west to River North for much better food at the same price.
9.
Experience Real Blues at Kingston Mines
Chicago is the home of the electric blues.
The Tip: Don't just listen to Spotify. Go to a blues club. Kingston Mines or Green Mill (Al Capone’s favorite hangout) are legendary. They are loud, gritty, and stay open until 4:00 AM. It’s a raw musical experience you can’t find anywhere else.
10.
Use the Pedway in Winter
If you visit between November and March, the wind cuts like a knife.
The Hack: Use the Pedway. It is a network of underground tunnels and overhead bridges connecting over 40 blocks in the downtown area. You can walk from your train to City Hall or Macy’s without ever stepping outside into the freezing cold.
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