Trip of The Month: Easy Guide to Chicago

The Bulls, a glass Skydeck, magic laundry stores, and a food cornucopia, it’s no wonder Chicago is a top place to visit for both business and pleasure. With so much to offer an easy guide to Chicago is an absolute must. Now don’t be fooled by the people who say they are from Chicago (*cough* suburb folks), take a stroll with me through the amazing city that has everything you need for every type of person.


Where To Stay:

You’ve booked your ticket and are planning to fly out to Chicago. Let’s talk about where you want to stay. It’s no surprise that your first place may be to look at is an Air-BnB. This is probably the best way to get a real-life sense of exposure to the city especially when trying to avoid the high-priced downtown hotels. When looking for the best neighborhoods to book an Airbnb your go to spots should be Lincoln Park, Lakeview, Wicker Park, and Logan Square.

On the other hand, let’s say you don’t want to stay in a random person’s home, because it sounds like the beginning of a bad horror movie- fair enough. My recommendation is to book a hotel in the Rosemont area. Yes- this is located 25 minutes outside of the city, however it is a 2-minute drive from the airport, and there is a blue line train that takes you downtown into the city and can also take you to and from the airport. Fast, convenient, and you get a wide variety of hotel choices what could better?

Glow Tip: Public Transportation is literally a life style in Chicago and one of the easiest and most convenient ways to get around. A 3-day ventra pass is only $20 which includes trains and buses all over the city. Plus, if you happen to lose your bus cards you can download the card on the Ventra App, which you can even use to track trains and buses as they come and go.

Where To Eat:

You’ve flown in and already checked into your new humble abode for the weekend. But you’re probably hungry from your flight and want some sustenance. Lucky for you Chicago has everything you can imagine for food…and I mean EVERYTHING.


Let’s not forget the most important meal of the day. Here are some of my top spots for breakfast; Ann Sather’s, Wishbone, Stan’s Donuts (because who doesn’t love a good donut), The Bongo Room, and one of my favorites – Hash Chicago. If you do decide to go to HASH make sure you try the Elote Hash, it’s the perfect combination of Mexican elotes combined with American hash…literally mouthwatering.


Now for your midday desire! There are plenty of places to get food, but if you are going to Chicago you should definitely try one of our iconic dishes, deep dish pizza or hotdogs. Chicago’s deep-dish pizza is offered at a variety of locations such as Lou Mallnoti’s and Giordano’s, but my personal favorite is Peaquod’s in Lincoln Park. Warning before you go it takes 40 mins to prepare a deep dish but trust me it is worth the wait, and still way better than NY style pizza.

Also, an iconic Chicago hot dog place known as Gene & Jude’s is a must to get your Chicago dog. It is open until 2 AM but be warned…. never and I mean NEVER ask for ketchup on your Chicago hotdog. I promise you these people will laugh so hard that you will leave the store from embarrassment.


Most Chicago dinner spots offer happy hour deals from 4-7pm throughout the city. Some of my favorite spots are the Slurping Turtle (for the duck fat fried chicken wings!!!), Seoul Taco (Korean Style Tacos), Las Tablas (Colombian Empanadas!), and if you’re feeling a night downtown Carnivale is the place to be.


THE BEST MEAL OF THE DAY; trust me when I say this list could go on forever with all the possibilities in this city. Limiting this list the top four places to go would be Firecakes Chicago (donut ice cream sandwiches..enough said), Molly’s Cupcakes, Jenis Splendid Ice Creams, and Bombobar.

Fun fact the bakers from Molly’s Cupcakes were on Cupcake Wars and they won!

What To Do:

Chicago has a spot for everyone! For the avid sports lover- go see a Cubs game, a Bears game, a Bulls game, or a Blackhawks game. All of which are surrounded by TONS of bars and restaurants for your pleasure. 

Not into sports? No problem- During your free time you could go check out the many museums of Chi-Town! There’s the Wonder Museum, the Field Museum, and the Planetarium. My personal favorite is the Museum of Science and Industry, because you get to hug a tornado and let’s be real… how often does that happen?

Check out the famous Sear’s Tower (Willis Tower) Skydeck. The view from the glass skydeck is breathtaking and a must see for a great Insta pic! It’s $25 to head to the top or $75 if you’re ballin and want to skip the line. 

For nightlife there’s bars all over the city! You want great Latin music – go to Escobar’s, yes walking in a back alley sounds creepy but the hidden gem is worth going to. Suite Lounge is a great hip-hop bar, and Estereo is the place to be for a Latin vibe. Three Dots and a Dash has its own exotic set of tiki drinks. Or head to a late-night show at the Chicago Magic Lounge – you’ll walk into a laundry room and have to find your way into the show!

And of course there’s the famous Chicago Bean, Garrett’s Popcorn, concerts in Millennium Park, and even boat tours!

No matter what you’re looking for, Chicago is a city for everyone. Trust me… this list is a very tiny portion of the cities endless possibilities. This small view will have you planning your next trip to the windy city in no time. 

Looking for more cities? Try Nashville!

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