Overpack. The days can be a bit tricky in the Windy City. Don’t rely solely on the forecast. Overpack and pay the extra fee for a bag to ensure you have enough pants, sweaters and jackets, even in May. You will thank us later.
Semi-plan your activities. Chicago has a ton to offer. Whether you’re into the arts, museums, historic buildings, beautiful parks, sports, music or the food scene, Chicago has it all. But, because the city is so spread out, you will need to plan accordingly. {Side Note. If you have Celiac disease, like Karen, you need to really take a deep dive and do some research. If you’re a Celiac, you know that Gluten Friendly and Gluten Free are completely different so, as always, ask your waiter/waitress. We found that while GF might be on the menu, cross contamination was a problem. Gluten free wasn’t as easy to find as we thought it would be.) In addition, a lot of Chicago restaurants offer takeout and delivery only.
Uber vs. Taxi. It seems like everyone In Chicago is an Uber or Lyft Driver. Seems like when you schedule one, they are always 4-5 minutes away. Taxis are in abundance also, especially in the touristy areas. We found that Uber is cheaper. Taxis start at $3.75 as soon as you open the door and it’s $2.25 per mile.
Hotels vs. AirBNB’s. This is very important. DO YOUR RESEARCH ON THE AREA BEFORE YOU BOOK. Read the fine print. Look at the map closely for attractions or events you want to attend and see if you can stay close. Chicago is absolutely gorgeous, and some areas are stunning but be aware of the area before you book your accommodations. You’ll be able to walk if you stay near the attractions you’re interested in.
Be Aware Of Your Surroundings. This is without question in any city. Be aware of the areas you walk into. Avoid dark back alleys at night. If you are planning to be out after midnight, make sure you stay with your group and always travel in well lit areas if walking. Never walk alone and never stop and engage in a conversation with someone asking for money. Keep walking and ignore the request.
If you are afraid of dogs, Chicago isn’t for you! Owners have their dogs out and about everywhere in Chicago.