Plan a Trip to Chicago: Things to Consider

Are you considering planning a trip to the Windy City? Chicago is filled with fun things to do all the way from its hopping nightlife to the glorious shopping on Magnificent Mile.

If you’ve never been to Chicago, we’re here to help give you some insight into planning your trip. The vibrant city has so much to offer, and you don’t want to miss a thing.

When is the Best Time to Visit?

Chicago lives up to its name, Windy City, as the winters there can be brutal. While Christmastime in Chicago offers up a fun, magical experience – you may want to opt to visit during milder months if you plan on doing a lot of walking.

Spring and early Autumn are wonderful times to adventure through the city of Chicago. The weather is much more enjoyable compared to its cold winters and humid summers.

It’s important to keep in mind that these times will be busier, though, simply because the weather is perfect for exploring the city!

How Should I Get Around?

Chicago has a great public transportation system, and it is used by a large portion of locals. Depending on where you’re lodging in Chicago, walking may be another viable, cost-friendly option. There are plenty of hotels located in the heart of Chicago, where vehicles aren’t necessary for getting around.

If you’re looking for luxury, Access Global provides top-tier professional drivers to drive you around town. This is a great choice if you want to maximize your experience in style!

Chicago’s Nightlife

Chicago has a bustling, exciting nightlife! The whole city comes alive after sundown, and if you’re looking for a place to dance or drink – there are a TON of options to choose from.

Underground Cocktail Club is like stepping back into a 1920’s speakeasy and is sure to give you an experience unlike any other. If you’re looking for some laughs, good vibes, and drinks – look no further than The Comedy Clubhouse.

If you want something a little more lowkey, check out Chicago’s Movies in the Parks or a gaming café like Snakes & Lattes.

For the Foodie

It would be a crime to not check out the famous Chicago-style pizza (Pequod’s is a favorite among locals!). There are plenty of restaurants to choose from that offer these cheesy slices of heaven, so you won’t have to look too hard to find them!

If you’re looking for some fine dining, Chicago doesn’t miss a beat. Restaurants like Oriole and Bellemore offer up an incredibly luxurious dining experience – backed by incredible, unique menu choices.

Shop ‘til you Drop

You could easily plan a trip to Chicago for shopping only. Chicago is known to be the home of luxury stores, and you can find most of them on Chicago’s Magnificent Mile.

If you’re looking to have a “Pretty Woman” experience, Chicago is the place to do it. Just be sure to check out some store options before you leave for the Windy City to maximize all it has to offer!

Plan a Trip to Chicago: The Rundown

Planning a trip to Chicago is such an exciting time! We know that it can be overwhelming with all the activities to do, but with proper planning you can get the best of the experience.

If you’re looking to stroll through the city streets comfortably, opt for going during the milder seasons. Checking out transportation before you land in Chicago will ensure you get to all the places you have on your list.

Lastly, research some options for nightlife, dining, and shopping before you go. You want to make sure you hit the best spots. Most importantly – have fun!