[ Planning Your Trip ]

Planning Your Trip

Deciding to go to Chicago? That’s the easy part. Make planning your trip just as easy with these helpful tips that outline when to go, what to do and what makes this city so unique.


About the City

“She is novelty; for she is never the Chicago you saw when you passed through the last time.” – Mark Twain

Yesterday, today, tomorrow. No matter the time period, this quote from Mark Twain rings true when one speaks of Chicago. The city is constantly changing, which means there’s always something new to do, place to go, or reason to visit. Perhaps that’s why over 50 million people do just that annually.

Its location along the shores of Lake Michigan gives way to its nickname—the Windy City. However, it’s famous for much more than just those blustery winds! With its rich history, Chicago has served as a gateway for industry, architecture, culture, and, of course, sports. In addition, the area also has all-natural pursuits for the outdoorsy type ranging from greenways to beaches.

As the anchor city of America’s Heartland, the Windy City bustles with people and commerce. At the same time, though, it has a modesty to it that’s pure Midwest. This combination is part of its charm, and no doubt, one of the reasons so many visitors flock to this town year after year.


As a resident member of the Midwest, Chicago enjoys all four seasons Mother Nature has to offer.

Winters in Chicago typically mean lots of snow and daily highs of 30-38°F. Come spring, the city starts to thaw. Flowers start blooming, the lakefront becomes livelier and temperatures rise to an average of 55-65°F. Of course, summers in Chicago generally keep pace with most of the Midwest with the heat rising to 80-90°F. Ironically, the summer season is also usually a wet one with June receiving more precipitation that any month out of the year. With average temperatures around 70°F, the fall season is an ideal time to visit. Not too cold, not too warm. In our opinion, it’s just right!

All of that said, Chicago weather can change on a dime. Sometimes it snows in May. Others, the summer season lingers and temps are still hot come October. As always, be sure to check the weather before your visit so you know exactly what to expect.

Chicago- architecture, métro, The L, transport

Getting Around

Chicago is a large city. However, thanks to its vast public transportation system it’s fairly to navigate. Traveling by rail and bus are the top ways to get around the city, not to mention the most affordable. If you’re familiar with the Chicago at all, you’ve probably heard the phrase ‘L’ Trains. If not, we’ll introduce you! ‘L’ Trains serve as the city’s subway system, but most of them are elevated, which is there the ‘L’ nickname arose. Two lines—the Blue and the Red—operate 24 hours a day. Plus, buses have more than 100 routes and they stop every few blocks. With that kind of public transportation system, you can easily see why getting around this city is easier than it seems at first glance.

Chicago is also a very walkable city. The entire downtown is mapped like a grid, with Madison Street dividing the city north and south and State Street dividing it east and west. Bring a comfortable pair of walking shoes. Then, you can make the sidewalks your friend while you visit the Windy City.

A large fleet of taxis serves the city as well. For this reason, it’s easy to hail a cab downtown, at the airport and throughout many Chicago neighborhoods. You can also e-hail a cab through the city’s mobile app, CHICABS.

On top of all those options, water taxis are also available in Chicago. These are a fun (and touristy!) way to not only get around the city but sightsee. Take a water taxi to sites like Chinatown, Museum Campus, Willis Tower, Michigan Avenue, Union Station and more.


As with any vacation, the cost to visit Chicago can range greatly. Keep these price points in mind for your trip planning:

Budget: $100 a day

Midrange: $100-$300 a day

Top End: $300+ a day

These costs include hotel stays, food, activities, and transportation.



When you visit Chicago, one thing is for sure: come hungry! The city is famous for its deep dish pizza that’s to-die-for as well as hot dogs (we’ll take everything, please!), beef sandwiches and Midwestern steaks. However, the city also features an array of fine dining with menus that span the globe. Not only are the ethnic offerings top-notch, Chicago is home to numerous award-winning restaurants and chefs. Do the Michelin or James Beard awards ring a bell? They’re prestigious in the culinary world, and in Chicago, they win these recognitions year after year.

What to Pack

What to pack for a vacation in Chicago varies greatly on the season in which you’re visiting. Yes, the city can get windy at times but there can also be snow, heat, or a fall chill to deal with. It’s important to not only dress for the seasons, though. You’ll also want to dress for your destination. That said, pack layers and pieces you can easily mix and match that easily go from daytime gear to nighttime dress.

This quick visitor’s guide will give you a head start on all your trip planning. Visiting should be easy, as should your time in the city. As a whole, Chicago has a lot to offer so get ready to discover more than you expected on your vacation to the Windy City.