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10 Things Only Locals Know About Chicago

Or, everything you need to know to enjoy the Windy City like a native.

By Lynsey Elve on September 18, 2016

Chicago IL
Chicago / Courtesy of Dave Wilson under a CC 4.0 license.

If you’re a Chicagoan, you know there are some specific “tricks of the trade” or “rules” to live by when navigating this great city. The weather is no joke; dinner reservations are a must; and you should make an effort to get “off the beaten path” for some great experience, just to name a few. Below are 10 things only locals know about Chicago — and things that you should adopt if you plant visit or move to the Windy City.

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1. Avoid the Red Line train before and after a Cubs game

The Red Line “L” train takes you right to Wrigley Field, which is fantastic and incredibly convenient, if you’re going to the ball game. If you’re trying to get anywhere else, it’s a nightmare. Wall to wall people squeezed in like sardines (and sometimes intoxicated), it can make your leisurely weekend train ride not so leisurely. If you plan to take the Red Line on a Cubs game day, spring for a cab or ride a Divvy bike. You’ll thank us later.

2. You’re going to need a great pair of winter boots and a solid jacket

Chicago is freezing in the winter. The average high is 29 degrees F and the low is 12 degrees F. The wind is brutal and it’s not uncommon for the snow to be knee-high. (You get a heavy snow about once per week.) If you’re visiting Chicago in the winter months, or if you live in the city year-round, it’s crucial you invest in an amazing pair of winter boots (knee-length recommended!) and a full-length goose-down jacket. Case closed.

3. Avoid Michigan Avenue on the weekends

The Miracle Mile is great, but it’s overrun with tourists. If you’re looking for good shopping try the Armitage and Halsted shopping district or Chestnut and Rush Street shopping. Great stores and a lot less people.

4. The best restaurants are in the West Loop or Lincoln Square

Skip the chain restaurants on Michigan Avenue and travel to the West Loop or Lincoln Square for some of the best restaurants in the city. (And even the country!) Logan Square is a prime destination for the city’s best cocktails and culinary experiences (Longman & Eagle and Lula Café are two crowd favorites!). The West Loop’s Restaurant Row is also a crowd pleaser.

5. Forget Garrett’s Popcorn, try Berco’s

Garrett’s Popcorn is good, but skip the crazy long line and throngs of tourists and visit Berco’s instead. Berco’s has a quaint storefront in the Armitage shopping district and the flavors are just as good or better than Garrett’s. If you’re feeling luxurious try its Billion Dollar Popcorn for $250.00 per tin. According to the website, it’s made from Organic sugar, butter from Vermont Creamery, Nielsen Massey Bourbon Vanilla and Danish island Laeso, the most expensive salt in the world. For us regular folks, the “Best Caramel Corn Ever” and the “Big Time Butter” flavors are out of this world and less expensive.

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6. Make dinner reservations

Do not try and “fly by the seat of your pants” on a Saturday night in Chicago, unless you’re interested in dinner at McDonald’s. Chicago is a foodie town with some of the best restaurants in the world, with limited seating. Those restaurants get booked up quickly, very quickly. If you want to enjoy a nice dinner (especially in the summer) be sure to get a reservation at least 5-7 days in advance or you could experience a 2-4 hour wait, or be turned away at the door.

7. Visit in the summer, not the winter

Chicago is hands down the best city to visit in the summer, with too many beaches, festivals and open air restaurants and rooftops to count. However, in the winter it’s cold and when I say cold I mean freeze-your-face-off cold. You can visit the museums during the colder months, though, and of course still enjoy the nightlife. But the best time to visit is in the summer, hands down.

8. For Chicago’s best pizza it’s Connie’s or Pequod’s

There is a lot of competition and opinions surrounding Chicago pizza. Most people tend to visit Lou Malnati’s or Gino’s East and both of those options are delicious, but very busy with long long waits. Connie’s Pizza opened in 1962 on the south side of Chicago. It has a great downtown storefront just a few blocks away from Michigan Avenue and the pizza is out of this world. Pequod’s Pizza has a cult following. It doesn’t do deep dish, but it has great thin crust and pan pizzas with a special caramelized crust. It’s off the beaten path in the Lincoln Park/Sheffield neighborhood, but worth the cab or train ride.

9. Explore the Chicago Cultural Center

On a weekend, The Field Museum, Shedd Aquarium and others are packed with families and kids. One amazing museum that typically isn’t packed is the Chicago Cultural Center. It has world’s largest stained-glass Tiffany dome and other handcrafted decor, not to mention oodles of free activities such as art exhibits and theater performances.

10. Walk the 606 trail

The 606 is an abandoned railroad line that has been re-developed into a 2.7 mile multi-use recreational trail and park that spans across Chicago’s northwest side. It is a living work of art with permanent and temporary collections. It’s new to the city and has only been open a little more than a year. Check it out!

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