Destiny In ChicagoI had the pleasure of visiting the Windy City for the first time this past weekend! The city dazzled me with a lively downtown scene, deep dish pizza, hipster coffee joints, and a chance to catch up with a childhood friend. While I was packing for Chicago, I assumed the weather would be cold and packed heavy, which I was extremely thankful for. The famous Chi-town winds makes a 40 degree spring day seem like the dead of winter to this Vegas-born chick. But besides packing recommendations, I also learned a few tips & tricks I would remember for my next adventure when traveling to Chicago.

Tips for Traveling to Chicago


1. Check the Weather Forecast

If the weather forecast says 40 degrees, don’t forget to add the wind factor. I recommend bringing layers, gloves, scarves, a hat, and a variety of jackets to choose from depending on the weather for the day. Of course the weather will be different in the summer, but always pack an umbrella just in case.

The Giant Bean Chicago

2. Plan Your Transportation

When it comes to getting around town, there are so many options available to tourists including Uber, Lyft, Taxis, Trains, bicycles, and walking. Using Uber will always be my first choice, but ride fares can rack up quickly if you have a busy day ahead. The train is convenient if you use Google Maps and make sure you go up or down the stairs on the correct side of the tracks because you can’t switch sides. I highly recommend getting the 3-day CTA pass because it will end up being less expensive than a daily pass and it works for bus rides as well. Lastly, I would recommend using the Divvy bicycles for a day if you have time to cruise lakeside. The bicycles are $10 for 24 hours and offer a memorable experience that can provide transportation and enjoyment all the way from the Zoo to the Planetarium.

Divvy Bike Chicago

3. Book Show Tickets In Advance

Seeing The Second City live or a Broadway performance in Chicago will be a highlight of your trip, but don’t wait to book your tickets because shows sell out fast. I would recommend booking at least 2 weeks out so you can secure good seats at the best time that fits your schedule.

4. Save Time to Eat

Dining at all of the restaurants in Chicago was my favorite part. Make time to eat every meal at a local restaurant you can’t find back at home. From brunch at Wildberry Pancakes and Cafe to dinner at Giordano’s, the wait times are long, the places are packed, and the food is amazing. We waited on average 15-45 minutes before every meal and if you are getting deep dish pizza that adds another 25 minutes before you start the main dish.Chicago PizzaWormhole Coffee Chicago

5. Take Advantage of Free

There are quite a few activities in town that are completely free like The Lincoln Park Zoo. We also enjoyed walking around Millennium Park, Grant Park, and the hipster area surrounding Wicker Park. Take a picture at The Giant Bean, see the lions at the zoo, window shop around Wicker Park and soak up the sun and wind because all of the free activities are almost all outdoors.Destiny & Kyle Chicago

6. Get the City Pass

If you are looking to do all of the tourist things in Chicago, get the City Pass online before you go anywhere. The lines to all of the experiences are extremely long but you will save time and money buying the City Pass. Although it costs $98 you will hit every tourist hot spot in town. The best part is, it also acts as a fast pass to skip the lines which sometimes can wrap around the buildings. We waited an hour to get tickets to the Skydeck at The Willis Tower only to find out it would be another 30 minute wait to get up to the top. After that experience we decided the City Pass was the only way to do experience it all.

7. Be Safe

There were only a few times I felt unsafe in Chicago and both times were at the train stations. I would avoid the trains and buses after 9pm and avoid the south side all together. Ladies, I recommend having a cross body purse you can hide under your jacket. Don’t carry cash, you really don’t need it for anything and it’s never a good idea to give money to anyone asking because it could be a scam to get you to open up your wallet.

Altogether traveling to Chicago was a memorable experience and knowing these tips for next time will make our second vacation even better! If you have tips of your own or favorite places of your own, please share them in the comments. 

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