Here’s What You Need to Plan Your Trip to Chicago

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Here’s What You Need to Plan Your Trip to Chicago

Chicago. The Windy City. If you’ll be visiting these historic crossroads of the Midwest, you’ll find so much here – from the (in)famous deep dish pizzas to the dynasties of the local Bulls and Blackhawks, to a thriving local music scene and one of the nation’s most formidable skylines. With so much to see and do, it can be easy to overlook other parts of your itinerary. Thankfully, we’ve got you covered. Read on and check with us as we go over everything you’ll need to plan your trip to Chicago.

Method of transport

Specifically, this is referring to how you will get into Chicago – whether it is driving in, riding a bus in, taking a train in or flying into one of the many airports of the Chicago area. This is important to note for multiple reasons – this will determine which conditions to monitor prior to your trip whether it is weather or freeway traffic, what to expect while traveling between having wi-fi, available bathrooms or not, and most importantly – point of arrival. Yes, there are public transport and taxi services around the city, but your exact arrival point can make a big difference for those who are traveling and a bit more conscious about time or distance traveled. 

Which Airline Will You Be Taking?

This is especially relevant for those flying with a United States based airline, what with the recent spike in cancellations, delays and disarray impacting American airline operators. (Not to be confused with the specific airline of the same name, this impacts all US Carriers from Spirit to United.) It is an important choice to weigh to have a better idea of where in O’Hare you’ll be arriving, to gauge what kind of service you’ll expect, as well as the customer service options you should expect should the worst come to happen (delay, overbooking, lost luggage, etc). 


This is another very important option that will significantly impact your trip. Both the accommodations themselves will change a lot about how you rest and sleep in between journeys, as well as most importantly – impact the logistics! That is, how you will be getting to and from airports, attractions, etc. Whether it is staying with family, through airbnb or at a hotel, this is another super important detail to consider to also help budget properly, understand any constraints on your living situation while in Chicago, or even other smaller details such as what can you bring, when is check out time?

Lodging for Your Car… (Parking)

If you’ll be getting around primarily via car or private vehicle, this is definitely a step worth looking into before your trip! Parking can be very rare and expensive if you decide to wing it on this step, and can eat up a lot of your wallet and your limited time in Chicago – especially in places like downtown. To beat the hassle, knowing where you’ll park ahead of time can not only help with navigation and be a huge boost in planning – but also genuinely save tons of money! Garages and lots favor booking in advance, and the stressful holiday practice of circling the city, scanning for an empty spot (and then figuring out how to pay!), complicated city parking signs… it’s all irrelevant when you secure parking for your car ahead of time. We recommend sites such as Onairparking or Spothero for the most flexible, easy to use services and best customer service support. The latter being huge when traveling to a large, unfamiliar city for the first time. 

Transport Around the City

Of course, this might be precluded altogether if you decide on not driving at all! With a decent commuter rail service, availability of taxis, buses and scooter/bike rental services, if you’re visiting in a warmer season or fancy yourself to public transport/biking it, you could potentially save a lot of trouble and money normally associated with having to maintain a vehicle during your stay in Chicago. If not to save money on a car altogether, it is also good to be aware of other transport options around the city also in case of emergency, or to just economize on your vehicle in the best way possible. In a city as large as Chicago, you’ll find more than one way to get around the largest attractions, and in some instances, parking farther out at a cheaper garage can make all the difference. 


This one cannot be overstated – check the weather! The Windy City is famed for experiencing all four seasons. What might not be as commonly known is the severity of some of these seasons! A combination of an extreme continental location combined with a lakeside effect makes for some absolutely insane weather phenomena – very, very important to consider in all plans. Winter snow and blizzards can reach a bone-chilling cold for even the most frosty visitors, and may even impact indoor plans or getting around the city if conditions are severe enough. Summer heat also should not be discounted – despite the relative northerly location of Chicago, the location in the Midwest can still provide for unexpectedly hot temperatures – sometimes dangerously so. This is also of note for those with outdoor activities or even just for seemingly short trips around the city. In the right (or wrong) weather conditions, even the smallest trips outside of a well heated/air-conditioned home/car can feel like a difficult eternity.


Also related to this is to pack accordingly! And for those visiting from outside of the region – do invest in proper winter clothing and equipment before you come! The scramble to get cold weather clothing can be difficult, stressful, maybe not even possible in the worst conditions, and is also generally not advisable as the thing to do immediately after a long plane flight. Pack warm and comfortable, or light and cool for the appropriate season and weather of your trip – future you will thank you. 


And finally, tickets and reservations. Not just at restaurants, but at many of Chicago’s biggest and baddest attractions, tickets and reservations are either increasingly necessary, or also huge money savers. Not to mention, the heartache and pressure saved when traveling during peak tourist season – no need to worry if you’ll get in on time or if it will fill up before you arrive when you’ve already saved yourselves a spot. 

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