Planning a Trip to Chicago

Flights

To start I needed to find the cheapest flights. I used flights.google.com to find the cheapest flight out and compare prices on different dates (since we had some flexibility with our travel dates). I love this website, seriously a life saver! After I found the cheapest flight, I went to the airline carrier site (American) to book, since typically flights are cheaper straight from the carrier site.

Hotels

Finding a hotel was a little overwhelming since there are so many options to choose from! There is truly something for everyone. We stayed in the Marriott hotel on Magnificent Mile and it was a great location! Close to everything, the Riverwalk was about a 10 minute walk and restaurants and shops were on every corner, plus the area was safe!! There are plenty of Marriott properties in this downtown area, as well as other properties. I just typically stay with Marriott when I travel and I had points to use!

Transportation

Uber and the cost was going to be about $40 before tip one way (please tip your drivers!). The cost is about half that if you share the ride. You want to consider the time of day too, if you are traveling with Lyft or Uber on a work day during rush hours you will be sitting in traffic forever!

I looked into the Chicago “L” Train through the Chicago Transit Authority (CTA) and this was by far the best option for us! We were in Chicago for a week and wanted to go all over town, so we would be using the L train all the time, and that we did! We opted for the 7 day unlimited ride pass which was $28 each, plus the $5 fee to purchase a new Ventra card (the card you use for your fares). The Ventra card can be used for all L trains and all CTA buses which can get you to anywhere you are going within in the city and surrounding neighborhoods.

Is it safe? I always felt safe on the trains and buses.
We only used the bus a few times when needed and we only used the bus during the day. We used the L train both day and night, and as in most cities the crazies do come out at night so just don’t look like a tourist (less likely to be asked for money) and don’t make eye contact and you’ll be fine. During the day the trains and buses were perfectly fine, mostly people commuting to work or just locals getting around.

I suggest getting an unlimited pass. The 3 day is perfect for a weekend in Chicago (which is plenty of time to do everything). Had we taken a Lyft or an Uber from the airport we would have spent at least $80 just on transportation to and from the airport. We only spent $66 on transportation for the whole week for both of us combined!

*Bonus: If you need to get somewhere close to the river and want to take in the beautiful architecture while doing so, without spending $40 per person, take the Chicago Water Taxi! We wanted to see the architecture from the river but didn’t want to spend $40 each on an architecture tour, so we took the water taxi from the Riverwalk near Trump hotel, to Chinatown (then took the L train back since it was already paid for). We loved it! The boat was a double-decker and we sat on the open air top level (there was an inside too on the bottom level for colder months). Cost is $6 one way, $10.00 for an unlimited ride all-day pass, or $20 for 10 rides. I’d say the one way or the all-day pass is the most worth it, the L train is faster in terms of transportation, but for the ambiance the water taxi is much better.

Plan your Must Dos

There is SO much to do in Chicago (it’s like a mini New York City). There is great food, bars, shopping, sports, museums, Broadway shows, Comedy shows, kids activities, walking trails, etc. It’s easy to get distracted and forget/not have enough time to do the things you want to do. I did a ton of research before heading there and planned out what I wanted to do on certain days based on the areas we would be in. I’ll do a Chicago Neighborhoods post to show what to do and what to eat in different areas of Chicago.
I knew we wanted to watch a ton of baseball and go to the Hamilton Broadway show, so I planned our whole trip around those activities. I bought our Cubs, and Hamilton tickets ahead of time to ensure we had seats and to get a good deal. Many restaurants are busy all the time, so reservations are encouraged, so you might have to plan activities around your brunch or dinner reservations as well.
There are tons of Chicago Vlogs on YouTube, articles that you can search for, and of course a list of popular activities on Trip Advisor…or you can use my posts as a guide for activities/restaurants to visit in Chicago if you like the same things!

Take Aways

-Use Google Flights to compare flight costs.
-Stick with your favorite Hotel brand to stay (they likely have a hotel in the downtown area).
-Use the L train and city buses to get around (Especially during the day, at night can get a little sketchy), then unlimited passes are your best deal.
-Take the water taxi once, to take in the views on the river.
-Find a few things that you absolutely have to do, and plan your trip around those activities.