The Essential Guide to Mastering Chicago at KubeCon North America 2023

Posted: November 3rd, 2023 | Author: | Filed under: Uncategorized | No Comments »

When thinking about destinations in the United States, Chicago oftentimes takes a backseat to cities like New York or Los Angeles. However, Chicago is a world class city that offers so much – and for those attending KubeCon and CloudNativeCon North America 2023, there’s just too many things to do and see. Being as it is my hometown, I wanted to share my thoughts and recommendations so that you as a KubeCon attendee can make the most of your time in the “Windy City”.

Note: This guide is not meant to be comprehensive. There are entire books written about Chicago which go into further depth. However, it should provide key details that generally should be applicable to the masses.

Getting to and around Chicago

Chicago, being centrally located within the United States, makes it easy to access whether traveling domestically or from an international location. It also features a robust transportation network within the city that makes it fairly easy to get around. I, personally, do not own a car and for those attending KubeCon exclusively, there really is no reason to rent a car (trust me, you don’t want to worry about parking which not only can be hard to find, but it is also very expensive. More on that in a moment.

Traveling to Chicago

Chicago is well connected for those traveling domestically or internationally. It is the midwest hub for Amtrak, the passenger rail company serving the country, so most trains originate or terminate there. However, most attending will by flying in on one of the domestic airlines or from an international destination. Chicago is home to two airports:

Midway primarily serves domestic carriers, and in particular, is a hub for Southwest Airlines. But international routes are also available from Canada and Latin America.

However, the majority of attendees will be arriving at O’Hare. It is one of the largest airports in the world and is only one of five airports globally that has connectivity to every inhabited continent. I won’t lie that part of the reason that I do live in Chicago is the ease of access to the world.

For those traveling by road, several Interstate highways either terminate within the city limits or traverse the region. Though, as mentioned previously, parking either at hotels or in a parking lot does add up quickly.

Traveling around Chicago

Chicago is a well connected city and features multiple forms of transportation, both public and private, for getting around.

Public transportation is operated within the city by the Chicago Transit Authority (CTA) which operates buses and trains (subways). Most trains are elevated and the system is called “The ‘L’” (short for elevated), but some do operate underground in “the loop”  The loop is the central business district where most of the CTA train lines converge. Train lines are color coded and feature a flat fare ($2.50) regardless of the distance. However, if entering the system at O’Hare airport, the fare is $5.00. Because no better way to make a few extra dollars than by charging unsuspecting travelers.

Though taking the train is highly recommended from O’Hare as the primary highway into the city is undergoing a multiyear reconstruction project and the traffic (which was already bad) is even worse than it was in the past. A robust bus network also runs throughout the city and the fare is $2.25. Transfers between train lines are free and two transfers are included in the fare between buses or trains within a two hour period. The full list of fares can be found here. Also, look into some of the pass options if you plan to use the CTA throughout the conference as 1, 3, 5, and 7 day options are available.

Unlike New York, which does not have good access to public transportation from airports, both Airports have direct connections to the CTA subway system. Midway is served by the orange line and O’Hare is served by the blue line. The blue line (along with the Red line) operates 24hrs a day. The rest of the lines vary slightly but tend to operate between 5AM and 12:30AM. 

I highly recommend using the CTA when arriving at O’Hare as it can take over an hour to crawl into the city (nothing is more painful to see than sitting in bumper to bumper traffic while the train speeds by) and fares can get as high as $100 at peak times. But, if arriving during the weekend before the conference, do note that there is bus shuttle service substitution due to construction. So, depending on the traffic conditions, you may indeed be better off finding alternate modes of transport.

Midway airport is closer to the city and only takes 25 minutes to reach the loop by train versus 50 minutes (when no construction is present) on the blue line.

Multiple forms of payment are accepted on the CTA. Ventra is the official transit card of the CTA and cards can be purchased at each train station. Contactless payment using a credit card, Apple Pay or Google Pay are also accepted.

If there is an interest to get out of the city entirely, regional train transportation is also available and served by Metra. The same Ventra card used by the CTA can be used as well for payment on Metra. One interesting fact about riding Metra is that drinking alcohol on board is allowed.

For those coming from international destinations, I will once again remind everyone that public transportation in the US is well.. subpar at best compared to the rest of the world. Especially these days in Chicago which like many US cities face both budget and ridership shortages, consistency is a hit or miss game. I highly recommend downloading a transit tracker or consulting the CTA website for when the next train or bus will arrive. However, there is a term called “ghosting” where the next bus or train on the tracker will fail to actual materialize. Especially later in the evening, don’t be surprised if you need to wait 20-30 minutes; even right in the downtown core.

Outside of public transportation, multiple ride sharing options are also available, including Uber and Lyft along with traditional Taxi’s. Divvy bike sharing is also available for those that want to traverse the city on two wheels.

The Venue

KubeCon is being held at McCormick Place, a sprawling conference complex a few miles south of the loop. Unlike past North American KubeCon events in Los Angeles and Detroit, most attendees will most likely be staying at hotels further away from the convention center itself as not only is it outside the central city core, but there are only a few hotels nearby.

Multiple buses serve McCormick Place along with two CTA subway stops (Cermak-McCormick Place on the Green line is the closest while Cermak-Chinatown on the Red line not much further away). Whether taking the bus or the train, be sure to be aware of your surroundings and get off at the correct stop. While Chicago is generally a safe city, the south side (where the convention center is located) traditionally experiences more crime compared to other parts of the city. Overshooting your stop can quickly lead you into some very undesirable neighborhoods very quickly. So, while I encourage you to venture out and explore the city, do so with safety in mind. Definitely follow best practices for any large city by traveling in groups, taking off your conference badge and just not looking like an obvious tourist. Following a few steps will ensure that you will not only have fun, but do so safely.

The Climate of Chicago

For those that attended KubeCon North America in Detroit in 2022, the climates between the two cities are comparable since they not only are at the same latitude, but are also only 200 miles apart. Given that it is November and looking ahead at the weather forecast, it is going to be far from beach weather. High temperatures are expected to be in the 50’s F/ 10 C with lows in the 40s F / 5 C with a chance of rain later in the week. Even though Chicago’s most famous nickname, “The Windy City”, is due to its politics, it lives up to its moniker as being a very blustery city due to the combination of sitting right along the shores of Lake Michigan, one of the Great Lakes, and the tall buildings creating wind tunnels. Be sure to pack for the elements. Keep in mind that the conference will have a coat and bag check on site where you can securely store your belongings during the event. The latest weather forecast for Chicago can be found here.

Chicago Food and Drink

You will not go hungry at all in Chicago. Period. There are literally a million options out there and there’s no way that I could include every single option possible. I’ll attempt to provide some of the highlights of places that I personally recommend, but know that there are both other options out there so use these suggestions as inspiration and then let your fingers do the walking….

Pizza

Chicago is famously known for its deep dish style of pizza. More like a casserole, it not only features a thicker crust, but an inverted method of layering on the toppings. But, while deep dish is the most famous type of Chicago pizza, the city actually boasts three (if not more) distinct genres of pizza: the aforementioned deep dish, stuffed and the lesser known, but my preferred, Tavern style (thin crust). Here are a few of go to’s when it comes to pizza:

  • Deep Dish
  • Stuffed
  • Thin crust
    • Almost all pizzerias in Chicago have a thin crust variety..

Personally, I can’t say there’s a standout thin crust pizzeria that you “must” try. There’s also a good chance that one of the colocated and/or parties will feature thin crust pizza as its much easier to serve for the masses. Though, keep in mind that both deep dish and stuffed pizza does take more time to prepare. So, be cognizant of the time that you have available for your meal.

Italian Beef

Chicago’s version of the roast beef sandwich features thin slices of beef on a french roll and optionally dipped in au jus. Giardiniera (hot sweet peppers) are the typical condiment that is placed on the sandwich. 

  • Al’s #1 Italian Beef (Various locations throughout the city, but the original location in Little Italy is the best [1079 W Taylor St, Chicago, IL 60607])
  • Mr Beef (666 N Orleans St, Chicago, IL 60654)

Hot Dogs

Chicago Hot Dogs are prepared using an all beef frankfurter that has been “dragged through the garden” and includes toppings such as neon green relish, onions, a pickle spear on a poppy seed bun. The only condiment that you will not find or receive on the hot dog is ketchup.

Portillo’s (Various locations throughout the region, but 100 W. Ontario St. Chicago IL 60654 is the location in the city) and is quite the experience. Superdawg (6363 N Milwaukee Ave, Chicago, IL 60646) is also popular as it is a classic American drive-in. However, it is both far from the city core, and really requires a car. But, given that hot dogs are fairly common in quick serve restaurants, you will find a variety of options out there.

Another option that is found in most hot dog stands throughout the city are Gyros due to Chicago being the jumping off point for the food in the United States.

Everything else…

After covering the most requested Chicago food genres , here are some other locations and cuisines to also consider.

  • Alinea (modern, multi course)  – 1723 N Halsted St, Chicago, IL 60614
  • Au Cheval (Gourmet cheeseburger) – 800 W Randolph St, Chicago, IL 60607) 
  • Billy Goat Tavern (Made famous on the sketch comedy show Saturday Night Live fame) – 430 N. Michigan Ave at Lower Level Chicago, IL 60611)
  • Mexican
    • Chicago has a large Mexican population. There are countless Taco and Burrito joints throughout the city that certainly hit the spot after a long day and night at the conference. Rick Bayless is a famous Chicago chef and he has several restaurants throughout the city for more gourmet options).
  • Greek/Italian
    • Greektown and Little Italy are very close to each other and not too far from the loop on the west side. Greek Islands (200 S Halsted St, Chicago, IL 60661) is a fantastic restaurant for real good Greek food. Mario’s Italian Lemonade (1068 W Taylor St, Chicago, IL 60607) is a great location for dessert, but has unfortunately closed for the season and is a must try during the summer months.
  • Chinese
    • Chinatown has a plentiful assortment of restaurants and is not far from McCormick Place. Like any Chinatown, there are restaurants of all different types, so one isn’t better than the other. Stroll through the neighborhood and let your eyes and senses help with the selection..
  • Steak
  • Indian
    • Devon Avenue on the northern part of the city (near my alma mater Loyola University Chicago) features several blocks of great Indian cuisine and other traditional Indian establishments. The downside is that is far away from both the loop and the convention center
  • Garrett’s Popcorn (Several locations throughout Chicago)
    • Known for “The Chicago Mix” which is a combination of caramel and cheddar popcorn
  • Eli’s Cheesecake (No standalone locations in the city center, but it is served at many restaurants throughout the city)
  • Stan’s Donuts (Several locations throughout Chicago)

For those looking for a drink, there are of course upscale venues of all sorts. However, one of the unique features of the city are the neighborhood bars – each with its own styles.

Last call in Chicago for the most part is 2am. However, several bars have been given the designation of being “late night” where last call is 4am. These exist due to the blue collar 2nd shifters. Though the list of late night bars are continuing to dwindle as the city looks to lower the number that are currently operating.

Chicago has several breweries with Goose Island being one of the most popular. Also, Jeppson’s Malört is a “unique” Chicago spirit. I leave the rest to you to find out more….

Arts/Museums

Chicago is a sophisticated city with a rich arts and culture scene and features world class museums. There are many options and most are fairly close to the central business district. Though my personal favorite is the Museum of Science and Industry (MSI) (5700 S DuSable Lk Shr Dr, Chicago, IL 60637). It’s located near the University of Chicago on the South Side of the city, but worth the trek and accessible from the CTA. Others to check out include:

Architecture

Chicago is filled with so much architecture throughout the city and the region – from the classic era to the most modern skyscrapers:

Miscellaneous

Finally, here’s an assortment of other attractions and venues that you can visit while in the city:

Whether KubeCon is your first visit or your fiftieth, I welcome you to the place that I have called home for half of my life. I hope that you take advantage of your time here and do hope that you explore something new or visit an old favorite. You will quickly understand why there’s no other place that I would want to live!

Red Hat will have a large presence at KubeCon! Be sure to swing by the Red Hat booth where I will be holding two live demo sessions (Wednesday at 10:30-11:30 CST and Thursday 13:30-14:30 CST) along with signing copies of my book, “Kubernetes Secrets Management”, Wednesday from 14:00-15:00! Feel free to reach out on Twitter or LinkedIn and hope to see everyone!

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