The Best Tips Before You Visit Chicago

Chicago was never on my short list of places to go. Sure, it’s the third largest city in the United States. Sure, they have pizza. Sure, it’s on a gigantic lake and has tall buildings. So what? Well, Steve and I went to Chicago this weekend to find out “so what?”, and we’re already planning a trip back! I’m glad we gave it a go, and I’m here to give you some tips we discovered to hopefully help you make the trip yourself!

Get ready to scrape the sky!

Getting There

First things first, right? You gotta get there! Here’s how.

Driving or Taking the Train

If you’re close enough to drive, Chicago is located right on I-90. Or, if you prefer to let someone else do the hard work, you can also take Amtrak from places like Milwaukee, Detroit, or even New York City! Chicago’s Union Station is located just across the river from Willis Tower.

Note: This is the airport train station, not Union Station!
Read on: The World’s Most Underrated Travel Destinations


For the rest of us, we’ll want to fly into either Midway International Airport (MDW) or O’Hare International Airport (ORD). Steve and I flew into ORD, since there are multiple non-stops on United between our home airport and ORD.

Be sure to book a window seat!
Travel like a pro: Tips for Flying United

Taking the Train to Downtown

Both airports are connected to Chicago via the Chicago Transit Authority (CTA). You can take the Orange Line from MDW, or the Blue Line from ORD. Tickets were easy to buy at the kiosks in the airport trainstation at ORD. Here is some helpful info:

  • $5 for one-way or 24-hour tickets (choose accordingly)
  • $15 for 72 hours (for a quick weekender trip)
  • 40 minutes from airport (compared to a 40-minute, $40 Uber ride midday on a Friday)
  • You can skip the kiosk and use Google Pay, Apple Pay, or Samsung Pay
Ready to ride the rails.
Read next: The Best Tips for Traveling on a Budget

Getting Around

Chicago is one of the easiest cities to get around without a car. That’s mighty helpful since we’re still seeing a rental car shortage! Check it out.

The L

If you’re staying farther out from the City, or if you need to get from one end to the other more efficiently, you might consider taking the “L,” or “elevated” train. The maps are quite easy to read, and if you get a little stuck on the kiosk (it was a little finicky for us!) or have a question, just ask a local. A Chicago police officer came over to help us out at the train station in the airport before we even had a chance to ask!

The L
Essential info: How to Plan a Trip


Chicago is remarkably pedestrian friendly, especially if you’re already staying downtown. The streets are laid out on a grid, so there’s not a lot of meandering to be done unless you’re walking along the curve of the Chicago River. Your phone’s GPS may have a hard time finding you among the skyscrapers, as our did, but for the most part, we found Chicago easy to figure out on foot. Just don’t forget to stop and enjoy the historic architecture, modern buildings, and iconic sites along the way!

Take in the iconic sites by foot
Read on: The Best Destinations to Visit Without a Car in the USA

The Riverwalk

Speaking of pedestrian friendly, don’t forget to enjoy the Riverwalk! It’s more than just a path along the Chicago river. There are several restaurants, seating areas, and, of course, beautiful views to enjoy! All the bridges across the river are pedestrian-friendly, and another fun fact is that they are also all drawbridges!

You’ll find arches like this denoting stairs to take you down to the Riverwalk below street level.
All those historic bridges are drawbridges!
Keep reading: Confessions of a Solo Female Traveler

Skydeck at Willis Tower (Sears Tower)

I don’t know about you, but I had to Google “What is the Sears Tower called now?” Ha! I knew the name had changed, but I had no idea as to the new name. Just so you know, it’s now called Willis Tower, and “Skydeck” is the famous spot to get photos. You only get 60 seconds on “the Ledge” for groups of one to three people. For groups of four or more, you’ll have a total of 120 seconds for the entire group. Tickets are $35 per person, as of October 2021.

Speaking of photos, I really thought the photo conditions would be better! I honestly don’t think it had anything to do with the time of day as much as just poor lighting in the building. You can see my photo below–it’s very dark! I brightened it up as much as possible, and lifted the shadows all the way up, but now it just looks funny. I wish I had looked up some tips during all that time I was looking up fun poses to do!

If you have tips to share, please comment below on this post so we can all do better than I did! Some tips I found online after the fact are:

  • Use the backlight function of your camera. (Honestly, I don’t know what this is, and I don’t have a professional camera, just my iPhone.)
  • Use a polarizer filter. (Again, I don’t even know what this is. I’m showing all my ignorance for you!)
Pro tip: Look up photography tips!
Bloggers are real people, too: The WORST Things I Did for the ‘Gram


Let’s get to the good stuff, right? Pizza! Chicago-style pizza is “deep dish” (not to be confused or synonymous with “think crust”), and has the sauce on top of, not under, the cheese and other toppings. We tried pizza from six of the most famous pizzarias in town, and we had some strong opinions. You’ve got to try at least one while you’re in Chicago!

Pro tip: Order ahead! Chicago-style pizzas take 45-60 minutes to make, and often there are long wait times just to eat inside the restaurant! So, manage your hunger if you’re dedicated to eating in a restaurant, or order a head online (all the pizzerias had an “order online” option) and take it to go!

Don’t pass up the “upside down” style of pizza!
More here: Where to Find the Best Pizza in Chicago

The Bean

There will be people in your “Cloud Gate” or “the Bean” pictures. Not only will there be people in your pictures, those same people and more will also be reflected off the Bean in your photo as well! It’s just part of the experience, so embrace it! Get your photos, and maybe offer to take photos for some of the people around you as well. Enjoy!

You will rarely find it all to yourself!

Want more? Check out all my Chicago and USA posts on my dedicated United States Page!

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