Chicago Travel: Everything You Need to Know

Q & A With a Native Chicagoan and Frequent Flier


Jessica Jurgenson is a native of Chicago and frequently travels, domestically and internationally, through the city's major airports. Here, she gives travelers headed to the Windy City her best advice, hottest tips and things to avoid.

Chicago has two major airports, what do I need to know?

O’Hare is an international airport and one of the busiest in the world. Midway is also an international airport, but smaller with more domestic flights and carriers.  You can usually score some pretty good domestic flight deals out of Midway on Southwest!

What’s the best way to get to and from the airports?

O’Hare is accessible via the CTA (Chicago Transit Authority) blue line and Midway via the orange line. Depending on where you’re going or coming from in the city, you’re looking at a $30-$40 taxi ride to or from the airport. Cabs are generally always available from the airports, but public transportation is super easy to use if you want to save a few bucks and are ok standing on a train and managing a suitcase. If you’re traveling later at night, however, I would recommend taking a cab. Chicago is a big urban area and, like any big city, the public transit is generally safe, but safer during day. If you are coming from somewhere like Minnesota or areas outside of Chicago, there are also Amtrak trains and the Megabus that run to the airports. These options obviously take longer, but it’s often cheaper than flying; and if you like the glorious scenery of the Midwest plains, it’s an option! If you plan to drive, keep in mind that we suffer horrible traffic here in Chicago, so plan to avoid rush hour.

Can you give us any insider airport tips?

At O'Hare terminal 1 there are several different security checkpoints. Checkpoint two is always a nightmare because it’s right in the middle where everyone converges. I recommend going all the way to the left. The lines there aren’t as bad because you have to walk further to get there. Also, the Starbucks in Terminal B is always busy, but is often the safer bet because the one in Concourse C is all the way at the very, very end of the terminal. Not sure when they will figure out that they need another one. Oh and of course, don’t miss the yoga room in Terminal 3!!

I’ve heard driving and parking in downtown Chicago sucks, any advice?

If you’re driving and parking, my best advice is to make sure the meters are paid! They are priced based on the area of the city and they take credit cards or coins. The meter police check frequently for expired parking and they will happily ticket you $50 if you are a minute over, so pay the meters! Aside from meters, there are a few services now like Park Whiz that will help you find a parking lot downtown. They will show you availability, prices and locations and you can actually book and pay for your spot, in advance, online. Or you can try your luck by driving around downtown, but I’ll warn you, it’s not easy or cheap to park in downtown Chicago, especially during the day or around the theaters. I’d say $20/hour for downtown parking is the average.

It sounds like driving and parking downtown for a non-local could be a nightmare, is public transit a better option?

CTA public transit is definitely the best means of getting around the city. We have an awesome public transit system that is heavily travelled by both locals and visitors. There are eight trains that make up what we call the ‘L’ and each line is a different color; red, blue, brown, green, orange, purple, pink and yellow. The system is easy to figure out and there is usually an attendant at each of the stations (though whether or not these people will actually be helpful and nice is somewhat unpredictable). The trains run above ground when you are outside of the city, and underground inside the city. Cell phones sometimes work underground, but don’t count on it. You’ll need to get a Ventra pass which works on both the buses and the trains. You can buy a day pass which is best if you’ll be using transit all day, or you can do individual rides. There are machines at each station where you put money onto the card (they generally take cash or credit). The card is a must for the trains and the buses usually take cash, but be warned, the locals get annoyed if you pay cash because it takes forever! One way fares on the ‘L’  and bus are $2.25 and any of the stations with free transfers will be marked. Unmarked transfers are $.25. For getting out to the suburbs, the Metra trains (Amtrak) are much nicer and I’m pretty sure you can bring your cocktail on board. The Metra will also take you to the lakefront, museums, zoo, sporting events and other places around the city.

Do you have any safety tips?

There will be homeless people on the trains and buses. They usually ask for money or food and want to tell you their story. Also, be smart about how you carry your belongings. Like with any crowded urban area, there’s the risk of pick-pocketing and “apple-picking” which is when someone specifically grabs your iPhone and runs off. It’s rare, but it does happen. Oh, and sometimes the ‘L’ smells like pee because people sleep on the train!

What are the chances of grabbing a cab downtown?

Cabs downtown are pretty easy to come by. Most cabs will take credit cards, but it’s always best to ask before you get in. Chicago cabs will also charge you an extra $1 or $2 for an additional person, so don’t be shocked when you see them tack that on at the end of the ride. Overall, cabs are a reasonable and safe way to get around the city. A lot of people have been using Uber recently, which is a rideshare service that pairs drivers up with people looking for rides. My boyfriend and I use Uber a lot because we live in an area where not a lot of cabs come by, so it’s the way to go. Keep in mind that Uber cars are not allowed at the airports though.

Is it safe to bike in the city?

We have the Divvy Bikeshare  in Chicago which is hugely popular; I have friends who use it all the time. It’s like Zip Cars but for bikes. You have the bike for 30 minutes and then return it to a different station, which are everywhere. I also recommend that people stay on routes with bike lanes. Some streets can get pretty fast and Divvy does not offer helmets, so make sure to bring your own if you take this option. Whatever you do, DO NOT TAKE A DIVVY ON LAKESHORE DRIVE! It’s a death wish and illegal! A Travelers Guide to Chicago -

Now for the fun stuff, what’s on your list of must sees?

So many! It depends on the time of year, of course and what you’re into, but here is a short list:

  • Take an Architecture Tour.
  • Don't miss he Museums. There are too many to list and they are all fantastic. Especially look for the 21+ events with music, cocktails, etc.
  • Millennium Park is great, check out The Bean, Grant Park and all sorts of cool art sculptures and ice skating in the winter.
  • Sears Tower (now known as Willis Tower but to Chicagoans it will always be Sears Tower). If you're not afraid of heights, go out onto The Ledge!
  • The Hancock building. Go to the top and have a cocktail and, if you have the cash, dine at the Signature Room. Oddly, the women’s bathroom has one of the best views of the city!
  • Michigan Avenue for the iconic scene and shopping.
  • Head to the Theater district for a show!
  • Navy Pier is an obligatory tourist trap, but they do have the Children’s museum and Ferris Wheel and it’s where all the boat cruises depart from, which are actually pretty cool, especially the ones at night that line up with fireworks in the summer on Wednesday and Saturday nights.
  • Check out the ethnically diverse and historic neighborhoods. You’ll find great meals in Chinatown, Greek Town, Little Village for Mexican food, Taylor Street for Italian and Devon (north) is where all the Indian restaurants are.
  • Eat!  We have amazing restaurants. My best advice is to pick a spot in advance and book ahead, the popular places need a good 3-4 week lead time.
  • Scope out the breweries. A lot of them offer tours.
  • For music head to the Metro, Aragon, Vic, Riviera or House of Blues.
  • The Lakefront Trail is perfect for a run or bike ride and the beaches are great for volleyball if you can secure a net!
  • Join us insane, Chicago sports fans for a sporting event, it’s really something to see and be a part of.


Any attractions you think are overrated?

It depends on your preferences of course, but for me:

  • Navy Pier.
  • Some of Michigan Avenue can easily be avoided, it’s always crowded and there are plenty of other cool neighborhoods to shop in, Bucktown and Wicker Park for example, where you’ll find more independent boutiques.
  • Some of the museums can be stupidly crowded, especially during the summer. If there are some you really want to see, go for it because they are worth it, just know that there might be thousands of other people with the same idea.
  • I’ve never done one of those, hop-on, hop-off bus tours but they look kind of silly if you ask me.
  • There are these water dog speed boats that people seem to love. I don’t get it. There’s nothing “Chicago” about them at all, but hey, if it floats your boat!


So, the weather….

Avoid coming in winter unless you are prepared for snow, delayed flights and cold. BUT, if you’re looking for deals on flights and hotels and enjoy things like football, hockey, concerts, restaurants, bars, shows, etc. then join us during the season, the holidays are very pretty here. Spring can still be cold but also wonderful; the city really comes alive that first nice day of the year.  Summer is probably the best time to visit. It’s our heavy tourist season though, so there are more people to contend with. And the heat and humidity can get pretty nasty, so prepare to sweat! Personally, my favorite time of year here in Chicago is the fall. The weather is comfortable and, though you won’t be chilling on the beach, it’s all around a fun time of year for Chicagoans. It’s my happy time.

Any last words of wisdom for travelers headed to Chicago?

Bring comfortable shoes! Being a tourist you will be walking A LOT. Also, be prepared for drastic changes in weather in a single day; that means packing layers and waterproof jackets and footwear. If you plan on going to restaurants, bars or clubs, men should bring closed toe shoes and long pants or jeans. A lot of places will not let guys in wearing shorts. In general, we are pretty casual here, but it depends on where you’re going; some places are quite trendy and you’ll feel out of place not wearing heels and a dress. If you come in winter, boots are smart. We wear our Hunters and Sorels without shame and thank our lucky stars that we purchased warm, waterproof boots!