5 Ways To Enjoy Chicago Over A Weekend

Our schedules doesn’t always permit for long haul vacations, but never forget, just stepping away from your everyday norm is a vacation. Sometimes we often overlook the gems that are here in the United States. There are plenty more cities other than New York, Los Angeles, and Miami. If you have a weekend to spare I would definitely recommend visiting Chicago. Though it is a city, it is not as nearly busy and crowded as New York and offers a ton to do along with good food. For me it was much more than just another city, it is a known stomping ground for our president Barack Obama, My favorite rapper, Kanye West and one of the greatest NBA players Michael Jordan. Here are 10 easy ways to enjoy Chicago in a couple of days.

When to visit

The best time to visit is between April and October, with June to August being the summer months, since the weather is between warm and hot. Chicago often have frigid winters, completely with white fluffy blankets of snow. If that’s your thing, then by all means go during that time, but that may diminish your expereince and accessibility to places. I went during October (mainly for a concert) and the weather was perfect to rock my jackets. The downside to this was not being able to visit popular landmarks like Lake Michigan, HOWEVER you can replace that with fun ice skating.

Getting there & getting around

Flights are inexpensive from New York and can be as low as $100 to Chicago O’Hare International Airport. It is also a great option for a road trip if you are in a surrounding state like Ohio and Michigan. What I love about Chicago is how tourist friendly it is. Once you arrive it is very easy to get around with the convenience of efficiency public transportation, walking, cycling and Uber’s. For their transit system, CTA, you can purchase a pass or pay $2.50 as you go.

1 Day CTA Pass for $10
3 Day CTA Pass for $20
7 Day CTA Pass for $28

Things to Do

1. CityPass Chicago

Remember I boasted about how user friendly Chi-Town is. They offer a City Pass that allows you into up to 5 attractions for $90 (UPDATE: $108 for adults, $90 for children under 12). This was 100% worth it as you save money, and don’t have to worry too much about what to do. This attractions can be spanned across the weekend. The pass are valid for 9 days if purchased form the box office or one year since the date of purchase if purchased online. Check out their website here to view attractions and if the any of them piques your interest.

This Pass Includes:

Shedd Aquarium – Priority Entry
The Field Museum – VIP Entry

Museum of Science and Industry OR 360 CHICAGO Observation Deck – Express Entry
I went for the 360 Observation Deck that included a drink

Skydeck Chicago – Fast Pass

Adler Planetarium – VIP Entry OR Art Institute of Chicago – Fast Pass

I chose the Art Institute of Chicago since that interests me more.

2. FOOD

You don’t have to walk far to run int good eats in Chi-town. Especially during warm months, you can find a ton of street foods and restaurants with decedent bites. Here are a few of my favorites that you MUST try.

24 Layer Chocolate Cake - When I think of Chicago, I think of Michael Jordan and the Bull’s. So it’s only right to visit his restaurant for dinner and don’t for get to get the 23 layer chocolate cake, 23 being his basketball number.
Harold’s Chicken- If you’re from my hometown of New York, then you know about Crown and Kennedy fried chicken. Harold’s is a Chicago staple. You must, must, must get your bucket of chicken oozing with their home made mild or hot sauce.
Garrett’s Popcorn- The perfect snack to munch on while strolling through the city. You can find a few of these popcorn shops around town and it would be hard to avoid a line. Grab my favorite, a mix of tongue dancing hot & spicy cheese and pecan caramel (I eat them separate lol) or create your own. You can either go traditional or go daring and try one of their exotic seasonal flavors like Buffalo Ranch, yummy!
Giordano’s Deep Dish Pizza- Like come on, did you go to Chicago if you didn’t get their infamous Chicago style deep dish pizza. Giordano’s is one of the famous shops, but feel free to give another restaurants a cheese. By the way, New York style pizza is still the champ in my book hehe.

3. The BEan, Millenium Park

I am sure you have seen this big silver bean like structure when you’ve searched for Chicago on the internet and social media. What’s the hype? We aren’t sure. We just know you should go as a keepsake memory of Chi-town.

4. Stony Island Art Bank

A book lovers dream come true. It is a short drive outside of Chicago, you would find the library of all libraries. A media archive, hybrid gallery and community center, Stony Island Art Bank is dedicated to reclaiming the Black community.

5. Buckingham Fountain

Located in the center of Grant Park, lies the enormous angelic Buckingham Fountain.It is amongst the largest in the world. What different about this fountain is that you would get a beautiful skyline in of the cities tallest buildings making it a visual cross over of city and elegance. The fountain is active from May to mid- October (best months to visit) and puts on a dancing 20-minute show every hour.