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Chicago: Towering Over the Windy City

Chicago is the third largest city in the United States and is absolutely full of great things to do. So it is no wonder that it is such a popular destination. But like all big cities, it can get pretty expensive pretty quickly.

ChicagoMy first tip for Chicago: If you plan on driving to the city, make sure you have a plan for parking! In my opinion, driving and parking in Chicago is just as bad as, if not worse than, Manhattan. I’ve stayed in both the center of the city and on the outskirts near the airport. In the city we had to pay $35 per night to park in the garage – and that was with no reentry; we left the car there for four days. When we stayed near the airport, there was parking available at the hotel, but even that was hard to come by!

We did find out that if you become a member at the Horseshoe Hammond Casino, they offer free shuttles to different locations in the city center. So if you stay at one of their hotels (or a nearby one), that would definitely help out! We didn’t end up taking advantage of the offer, but you can get more information here. Word of advice: Uber is your best friend in Chicago. If you do have to park, find a place where you can leave your car all day for one flat fee, then walk and take Uber to get around the city.

Gorgeous views

Signature RoomWhat’s the first thing everyone wants to do in a major city like Chicago? Go to the top of the highest building of course!

In Chicago you have two popular options for observation decks: Willis Tower (formerly Sears Tower) and 360 Chicago (formerly the John Hancock Observatory). Why Chicago buildings can’t keep their names is one of life’s greatest mysteries. Regardless, admission to either of those observation floors will cost you at least $20 per person and require you to wait in line for what could be hours. I have a better option for you – visit one of the bars or restaurants in 360 Chicago. You can get the same views – plus food – without waiting in line – for the same price, if not cheaper (it really depends on what you get to eat or drink).

When we went, we visited the Signature Lounge on the 96th floor. We ordered a drink each and split an appetizer. Yes, the drinks were slightly more expensive than I would have liked, BUT it wasn’t overly crowded, we still got to take lots of pictures, had drinks, and didn’t pay much, if any, more than we would have just to visit the observation deck. And looking on the 360 website, it looks like Architect’s Corner Café and Bar is now open too! They are located on the 94th floor and have more reasonably priced snack options.

Chicago for free

Another great thing about Chicago is that their zoo is FREE. Yes, free. I don’t make these things up! Parking, of course, is not free, but we already talked about that. The Lincoln Park Zoo is fantastic, and I’m not exaggerating when I say you could spend an entire day there. We easily spent 4-5 hours walking around and still didn’t see everything we wanted to. Since the zoo doesn’t charge admission, the zoo has several entrances/exits that you can walk right in and out, sometimes without even noticing. In the middle of the zoo there are some beautiful spots to relax in and enjoy the famous Chicago skyline. There are also some wonderful gardens to explore.


If you want to hit some of the city’s bigger attractions, definitely invest in a city pass that bundles several attractions together for a certain amount of days (my favorite is Chicago Go Card – and I highly recommend the architecture river cruise for a great history of Chicago with spectacular views). Or, if you’re looking to enjoy Chicago without spending much more money, visit some of the parks! There is so much green space in Chicago, it’s one of my favorite things about the city.

The most famous spot in Chicago is Cloud Gate in Millenium Park, affectionately known as “The Bean.” Yes, you’ll look like a silly tourist when you take lots of pictures with it, but yes it is worth it and so much fun! Nearby Crown Fountain, which shows peoples faces while spitting out water, is a fun spot for kids. There is also a music pavilion that hosts free concerts in the summer and several more fountains hidden throughout the city. Lastly, a trip to Chicago isn’t complete without a stroll down Navy Pier and a ride on the Centennial Wheel. Take the free trolley to get up and down the pier if your feet need a rest!

A drink to end the day

Small Town BreweryIf you are looking for some interesting places outside of the city that are worth driving to, I recommend Small Town Brewery (home to Not Your Father’s Rootbeer) and the Jelly Belly Factory (which offers FREE warehouse tours). I’m sure we will be back to visit Chicago again soon. I hope you enjoy it too!

Happy travels!


Towering Over the Windy City - A budget-friendly guide to Chicago - travel advice - Wanderlust on a Budget -

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