Chicago

Stunning architecture & world-renowned cuisine

Chicago is one of my favorite cities to visit because it offers so many exciting things to do, literally something for anyone! And truth be told I am no city girl, I am much more of a beach-vacation kind of gal, but this city has definitely won my heart. It’s one of the most beautiful (and cleanest!) US cities I’ve visited. Chicago is a vibrant area with a diverse music scene, culture, intriguing public art, world-renowned food, sports, comedy, endless shopping, and museums (just to name a few!). Which is why it’s the perfect destination for a long weekend, but has enough excitement to keep you entertained for a week or more. Chi-town can be done on any budget, even some of the top things to do are free or practically free!

Famous skyscrapers decorate the shoreline while all over the city you will find intriguing and iconic works of art, like The Bean (FYI it’s really called “Cloud Gate”). Sports, comedy, shopping, museums and culture also thrive in this “city in a garden”. And while blues and jazz may have a rich history here, the music scene has since become very eclectic. Music lovers won’t have a hard time finding a festival or concert to attend.

And not to sound like a foodie, but just the thought of the amazing food this city offers makes me want to book a flight. From Michelin star restaurants to local specialties, any palate is sure to be happy. And to be totally transparent, this non-meat-eating Jerseyite must admit to tasting a Chicago Dog! Even though I had not eaten beef or pork in 23 years (‘cept for that one rib-eating instance in ’10), when in Rome…errr Chicago, right?? And though I will probably not have another one, I will say it was good! Frankly between the french fries and seven hundred other toppings, I really didn’t taste any “meat”. Yes, there are delicious fresh cut french fries ON the dog. And now you see why I tried it.

Let me touch briefly on the great pizza debate (which may only exist in my head, but it is something I battle with often). I am an east coast chick so I grew up on New York-style pizza, with thin and crispy crust…but dannnng I don’t know if I could choose between that and Chicago deep dish, with its ooey-gooey cheese! Have you ever seen Lou Malnati’s epic cheese pull?! Yes, it’s a thing! And YES they ship! And I’m about to book a flight right now…

But I digress on the whole food topic. I will apologize now, I really love food.

Best Time To Visit

The “windy city” can turn to snowy city in winter months and can get crowded during summertime. Assuming you want to see as many sites as possible while you’re there, the best time to visit is spring (May/June) or fall (September/October). Prices on hotels and flights will be cheaper during winter (obviously), more expensive during spring/fall and most expensive during the summer months. If you’re cool with forty feet of snow, by all means check out Chicago in February for a Restaurant Week you won’t forget. Otherwise, go in the warmer months so you can really explore the city and see all that it has to offer.

Fun Fact: Even though it is nicknamed The Windy City, Chicago doesn’t even fall in the top 34 windiest US cities(!), according to USA Today.

Special Event Months

Let’s Talk Temps

I, personally, am a summer lover. And I love to visit Chicago during the warmer months when the temperatures generally fall between high 70’s and low 90’s. The most mild temperatures often fall around 70° in May and September, perfect for all the outdoorsy stuff Chicago has to offer. Note that temperatures drop fast, so the end of August could feel like fall already and the end of October can get even chillier. One thing to also keep in mind is that June can be rainy at times, so pick up a travel umbrella (just in case), if you are visiting then. If you love whimsical wintery fun, Chicago temperatures drop to around 30-38°F (high!) and snowfall can average 37 inches from December to February. Not exactly my idea of fun, but hey to each his own! I will admit, the Magnificent Mile would be a great place to do my holiday shopping…

Getting There

Flights to Chicago tend to be reasonably priced, you can usually get a good deal from any of the major airports. Apps like Hopper and Kayak allow you to track flight prices and will notify you when the price changes. My preferred search engine is Google flights. While these sites are great for tracking purposes, I would suggest booking directly through the carriers website (usually that’s where you’ll get the best price).

Getting Around

Getting around Chicago is a breeze. Walking around is the most resourceful way see the city and since the downtown streets are set up like a grid, they are easy to navigate. Considering it’s such a big municipality, traffic can get intense and parking can be a nightmare, making driving a less-than-ideal choice. Luckily Chicago has the second largest public transportation system in the nation, so between the rail line, busses, taxis, and uber there’s really no need to rent a car.

Quick Guide to the CTA

Stay, See, Eat

Now that you know you want to visit this awesome city, where do you stay? What do you see? What do you eat?! Check out my guides below to make your trip planning a breeze.

STAY

SEE

EAT

Money Saving Tips

Take a strollThis beautiful city is decorated with public art, has easy to navigate streets, and is sprawling with greenery making it perfect for a walk. So put your parking fees and gas money towards a fantastic meal instead! (Well thats what I would do!)

Hop a rideKnown for having one of the best public transportation networks in the world, Chicago is easily accessible by buses, subway and “L” train (elevated). And at under $3 a ride, it’s completely affordable. Taxi’s and Uber also provide a cheaper option than paying for parking.

Get a city pass If you plan on seeing the sites while you’re here, get one of the city passes (Chicago City Pass or Go Chicago Explorer Pass). You’ll get admission to several attractions at a discounted price, which is great if you want to see all Chicago has to offer.

Stay in the ‘burbsStaying in The Loop or Near North Side will cost you, but find a budget stay outside of these main areas (try Wicker Park!) and use public transportation to get quickly downtown for just a few bucks.