20 Reasons to go to Chicago Now!

1. It’s so Clean:

I know writing conventions tell me I should start with something really cool and interesting, but one of the first things I noticed about Chicago is how clean the city is. Unlike NYC where there’s garbage overflowing on every corner and people littering like it’s the local dump, Chicago locals take pride in their city and abide by the signs encouraging them to upkeep their surroundings.

2. The People:

The people in Chicago are friendly. As a native New Yorker, born and raised, we tend to be aloof and on guard at all times. Actually, I have a story to tell: I was walking into the Chicago Metro one morning and someone said “Good Morning” to me. I ignored him. I wasn’t sure if he was talking to me, but he was. He made his presence clear by saying good morning again, with a smile. My heart melted and I replied back to him with the same kindness he showed me. I am not used to people talking to me in NYC so it was a bit of an adjustment to warm up to him. I realized, there are some people in the world that are just friendly and want nothing from you. That was one of the many takeaways from my stay.

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3. Magnificent Mile Shopping:

I wasn’t sure what would be the big deal about Magnificent Mile. It’s just shopping, right? Wrong! My breath was completely taken away by this beautiful strip. It’s every shopper’s paradise. The stores are huge. Nordstrom’s, Neiman Marcus, Chanel, Louis Vuitton, super-sized Zara, Guess, Forever 21, you name it, Chicago has it. I couldn’t believe how beautiful it was in the flesh. Of course one of the most sentimental moments I had was going to the American Girl store. I know I am old enough to have my own kids, but it was my childhood dream to come here and I felt blessed to finally receive the opportunity to. So there you have it, magnificent mile shopping was so good, it brought tears to my eyes.

IMG_11784. Sports:

Chicago Bulls. Chicago Blackhawks. Chicago Bears. Chicago Cubs. Chicago White Sox. Any of these teams ring a bell? I almost forgot I was in the town of Michael Jordan.  I was supposed to see a Cubs game at Wrigley Field the weekend I visited but it rained. The tickets are super cheap starting at $20 bucks. Unfortunately, the locals I talked to had nothing great to say about their teams.

IMG_11095.The Beach:

In the midst of the amazing city, Chicago has a beach. Just to give some perspective it was less than 7-mins walking distance from my hotel and my hotel was located in the midst of their Downtown District. I went to Chicago during Memorial Weekend, and this was the first day the beach was open to the public. It seemed like the perfect picturesque view. Tall Sky Scrapers, overlooking the beautiful Lake Michigan with locals and tourists alike sunbathing and playing volleyball. I almost felt like I was in the American version of Dubai.

6. The Food:

Chicago has some good food. I had an array of delicious dishes, ranging from Jamaican to Seafood, but the food I enjoyed most, was the Deep Dish Pizza. First, let me say OMG. Then I can proceed to describe this beautiful creation. It’s definitely a deep-dish, much bigger than I anticipated. The tomato sauce is covered on top and the delish cheese is layered throughout. I added sausage and pepperoni and waited over an hour to get this pizza made, but it was worth it. I bought a small pie for about $24 and it lasted for a whole week. I made sure to bring it back on the plane with me because it was too good to discard. Whoever created this is genius. I went to Giordano’s but people later told me Lou Malnati’s Pizzeria is better.

Giordano's Deep Dish Pizza Chicago7. Lake Michigan:

Lake Michigan is Chicago’s pride and joy. The lake is massive and a beautiful teal blue, it’s surrounded by tall immaculate buildings along Lake Shore Drive. One of the activities I did was take a tour along the lake. I took an architecture tour of some sort, although, I was told the tour would encompass fun facts and attractions. The water is cold (it splashed on me and my camera at one point) but adds eloquence to the city.  I shudder to think what Lake Michigan turns into during the winter months.IMG_1099

8. The Architecture:

I was amazed by Chicago’s architecture, and this is definitely a feature that the city is proud of. There’s a hybrid between the new and old buildings and Chicago once housed the tallest building in the world (Willis Tower) before the Burj Khalifa was built in Dubai. Now the Willis Tower is the second tallest building in the Western Hemisphere since the Freedom Tower was completed this year.

IMG_11409. The View of Chicago:

The view on the 103rd floor of the Willis Tower is phenomenal. I went to the Sky Deck at night and was captivated by the glistening lights and bustle of the city. From the deck, I could see the stadiums, the lake and other buildings on the horizon. After waiting on a long packed line, I got to the transparent box aka the sky deck that feels like you are walking on air, 103 stories high. If you are afraid of heights this attraction will freak you out!

10. The Chicago Theater:

I didn’t get to see a show at the Chicago Theater but I did pass by this gem and it’s amazing. I almost left Chicago without seeing this but as I was walking to the train station, headed to the airport, I saw the theater lights in the distance. With my suitcase in tow, I walked almost 10 blocks and was enamored by the Chicago Theater sign. So happy I could cross this off my bucket list.

IMG_135611. Chicago Stepping:

Taking a Chicago stepping class was important to me. Chicago is the birthplace of this artistry so I thought it would be awesome to take classes from the best. I found 2-dance classes but their beginner courses seemed to take place on Tuesday’s. Check out Crosstown Steppin and Steppers USA if you’re interested. However, there’s a steppers group in NYC that taught me the basics and I took the course for about 6-months. It was so much fun.

12. The Art Institute of Chicago:

The Art Institute of Chicago is the #1 Art Museum in the World, which was even more reason for me to add this to my itinerary. I went around noon on a Sunday. There was a long line outside of the museum, but I got in within 15-minutes. Ticket prices vary based on if you’re an in-state resident or not. Of course, out-of-state residents pay more. The cost for entry is $23. I decided to start on the top floor and work my way down. I started in European art, since it’s my least favorite and progressed into impressionism. Surprisingly I enjoyed the European art exhibits. I then made my way to the exhibits I knew I would love including modern, contemporary, photography, and African art. I must say, this was one of the best museums I’ve ever been to.IMG_1257 IMG_125413. The Museums:

I had to give the Art Institute its own reason to visit Chicago because c’mon it’s voted the #1 Museum in the World, but that shouldn’t take away from the other museums housed in this amazing city. I also had the chance to visit the Museum of Contemporary Photography and the  DuSable Museum which is an African American history museum. I came across the Chicago Cultural Center as well which is across the street from Millennium Park. The museums in Chicago are superb. Make sure to research the days where entry into the museums are free, although some museums just ask for a donation. What I didn’t get a chance to see was the Hull House, which is a staple in American history.

14. Navy Pier:

Navy Pier is a sort of amusement park in the heart of the city. There’s a Merry-Go-Round and Ferris Wheel as well as places to eat like BubbaGump and Margaritaville. There’s also the famous Garett’s Popcorn and Giordano’s.

Navy Pier-Travelbyky15. President Barack Obama’s Home:

Before Barack Obama became president and moved into the White House he lived in the Kenwood section of Chicago. Although you cannot go inside of his home (it’s highly secured), you can admire his humble beginnings from the outside.

16. The Bean (Cloud Gate):

Like every other city in the world, Chicago has the go-to attraction that signifies you’re there. In Paris it’s the Eiffel Tower, in NYC it’s the Empire State Building, in Chicago, its Cloud Gate. Cloud Gate or the Bean is a silver sculpture in Millennium Park that reflects the whole Chicago skyline. It’s made out of stainless steel and people love to go there to take pictures and admire the shape of this bean-like structure.

The bean17. The Music:

There’s music all around you in Chicago. Homeless men singing the blues, young men drumming on containers and dancing to the beat. There’s also a lot of jazz and blues clubs including Kingston Mines which plays classic music that takes you on a trip back in time.

18. Love Jones and other classic movies filmed in Chicago:

Love Jones is my favorite movie and the primary reason I visited Chicago. I wanted to see where Darius chased after Nina in Union Station and where they had their special date nights. Yet there are other classics that were shot in this city including My Best Friend’s Wedding at the Drake Hotel and the classic movie turned series on Showtime Soul Food.

Love Jones

19. It’s Kid Friendly:

Chicago has so many things to do for children. There’s the Lincoln Park Zoo, the Children Museum, Shedd’s Aquarium, and Adler Planetarium. I also walked by the Maggie Daley Park which I thought was fabulous. Maggie Daley was the mayor’s wife who died from cancer (I learned this from a local), the park was created in her name and it is fabulous. It’s located in the center of the city along Lake Shore Drive. The backdrop is the city skyline and the playground is imaginative.

20. Chicago Photography and Street Art:

The art in Chicago left me speechless. What I loved most is how Chicago’s art incorporates culture and diversity. I went to see the Dandy Lion Exhibit that sought to show black men in a different light other than the stereotypical “thug-like” exterior they supposedly give off through photography. The aim of this exhibit is to re-articulate Black Masculine identity. The subjects dressed nice and were overall well-rounded and complex individuals. I  got the chance to check out the Love for Sale exhibit at the Chicago Cultural Center, which was epic. Overall, the street art in Chicago stopped me in my tracks. Beautiful installments, sculptures, and graffiti art are sprinkled throughout the windy city.

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Ky Takes Chicago Part III

I took time in the morning just to relax. It was Sunday, so I read my bible, prayed and sat in silence—completely left with my thoughts. I was at peace. My first stop would be the Art Institute of Chicago. My plan was to get there by 10:30am when it first opened but once I got outside on Magnificent Mile, I was entranced by the liveliness around me.

I decided to walk to the American Girl Place. When I was around 10-years old, my mom planned to take me there for my birthday. I was so excited. However a few weeks into planning, she realized she couldn’t afford such a pricey trip. For me, it was one of those childhood heartbreaks. I acted like it was ok, but I was disappointed. When I got to the front of American Girl, I just cried. Growing up, my mom wanted to give me so much but financially she was limited. I felt so blessed to know God had exalted me to a position where I could make some of my dreams come true. It was the most therapeutic tears I have ever shed. I walked in and acknowledged all the beautiful dolls. There were hair salons and restaurants for the dolls and mini clothing boutiques for their clothes. Mother and daughters surrounded me. It was special, to say the least. I proceeded to some big girl (window) shopping at Neiman’s before heading to the three museums I wanted to tackle:

  1. Art Institute of Chicago
  2. Museum of Contemporary Photography
  3. DuSable Museum

AMERICAN gIRLAmerican GirlIMG_1189After my tour of Chicago’s museum, I planned to have a nice dinner to conclude my weekend. I got dressed and went out to the Wild Hare. In the movie Love Jones, Darius and Nina spent the night dancing to live reggae music at this spot. I wanted to recreate the same scene or feeling. When I first got to the restaurant there was a soccer team enjoying beers and a few couples on date night. I asked for a table for one and enjoyed a delicious Jerk Chicken plate with an ice-cold drink on the side. The music was epic, old school reggae that reminded me of my childhood (My mom and dad loved this kind of music). There was one last thing on my itinerary that I did not get done—The Chicago Theater. I wanted to ask my cab driver to drop me there but it was getting late. Eh, maybe ill come back in the future to see it.

The Wild Hare The next morning on my way to the train to get to the airport, in the distance I saw a sign that said CHICAGO—Wait was that the theater? With my suitcase in tow, I walked about 10-blocks along State Street until I was close enough to see it for sure. My trip to Chicago was officially complete.IMG_1356

Ky Takes Chicago Part II

Day two in Chicago started out in a bit of a frenzy. The person I was traveling with decided to head back home so now I was a solo traveler in Chicago. After I got over the initial fear of being alone, I found freedom in the whole situation. I moved out of the Airbnb apartment and found lodging closer to all the action. I was in the center of the Magnificent Mile. Luckily Jack, my Airbnb host, was nice enough to drive me to my new hotel. Once I checked in to the Inn of Chicago, I decided to walk along Michigan Avenue to explore.
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Almost immediately I came across Lake Michigan on the DuSable Bridge. I walked downstairs to see if I could get in on the boat action happening on the lake. I noticed there were a few boat tours and I figured taking one would be a great way to learn more about the city. All of the tours were sold out until 5:30PM which meant I had 3-hours of free time.

Magnificent Mile

I headed straight to the Bean in Millennium Park. It was actually pretty cool. The bean is made out of silver steel so it’s like a mirror of some sort—it reflects the city skyline as well. People gather from all over the world just to touch it and get a picture with it. I even found myself envious that I wouldn’t get the picture I wanted so I decided to take selfies until two nice ladies took my full-length pic for me (the struggles we have nowadays…millennials).

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From The Bean, I headed across the street to the Chicago Cultural Center. I stayed in there for hours exploring the exhibits. The architecture was beautiful. There was one specific exhibit that I loved called Love is for Sale: The Graphic Art of Valmor Products. What I loved about this exhibit is it raised awareness about the conversation of beauty in advertisements when catered to black women (and some men) back in the day. The ads promoted bleaching creams, wigs, and attaining “good hair” with Valmor Products. I’m always amazed by the ads of our dark past. Some of them were offensive and would make me feel inadequate as a black person (if I lived during those times).

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My tour of Chicago via Lake Michigan was the perfect way to get more acquainted with the city. I learned about the architecture, took in the beautiful views and just enjoyed the amazing weather. If you’re ever in Chicago, you have to take one of these tours on Lake Michigan.

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My day wouldn’t have been complete without a Deep Dish Pizza for dinner. I waited in Giordano’s for an hour before my pizza was ready. It was a total of $24 but so worth it. I was so exhausted by my day that I decided to take my deep dish back to the hotel. Let me just say this, deep-dish pizza is the best food creation on the face of this earth.

Giordano's Deep Dish Pizza Chicago

Ky Takes Chicago

When I first arrived in Chicago, I became enamored by all Chicago had to offer. O’hare airport is really nice. The passageway leading to the train station is adorned with neon lights that change colors as you walk. This was a trip meant for exploration. I didn’t want to take a cab into the city, I wanted to be like a local and take the train. It was 20-stops on the Blue line.

O'Hare Airport

I got off the train at Jackson Street and took a bus to my Airbnb apartment. I would be staying with a man named Jack. He lived in a condo on the South Side of Chicago along Michigan Avenue. When it was time to get off the bus Jack was waiting at the bus stop to greet me. It was wonderful. Jack’s apartment is beautiful. It has white decor, with pictures of Chicago hanging along the hallway walls. The apartment is treated just like a hotel. He had slippers waiting for me and a welcoming name sign on the room door. The continental breakfast was a plus as well. He mentioned he kept a camera in the kitchen which made total sense, I always wondered about the safety of Airbnb hosts. The view from Jack’s apartment is also amazing.

Airbnb

One of the first things I wanted to do was to visit the Navy Pier. It was about 20-minutes away from the apartment. I got on a bus then took a cab. To be honest, I was quite underwhelmed by it. It was still under a lot of construction, but the views from the pier were magnificent. Lake Michigan is such a beauty.

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From the Navy Pier, I went on to the Sky Deck Chicago in the Willis Tower. The Skydeck is about $19 and it’s an experience. There are two noteworthy rooms that you must go threw before you take the elevator to the 103rd floor. The first room is a sort of pop culture room, exhibiting everything that Chicago is known for including the Chicago Bulls, President Obama, and Oprah. There’s also a room where you can watch a video on the history of the Willis Tower and how it came to be. Finally, you are led along a hallway to elevators that take you to the 103rd floor. Once on the observation deck, you see the city like never before. There’s thousands of tourists there, all waiting to get a chance to stand on the sky deck.

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A Love Jones Lover Chicago Bucket List

Have you ever watched the movie, Love Jones? It’s by far one of my favorite movies. Larenz Tate and Nia Long play Darius Lovehall and Nina Mosely, a couple who live in Chicago and go through the ups and downs of a pre-social media relationship. The two have a love for the arts and poetry and an undying passion for each other. Chicago is the unofficial main character of this movie as the places they frequent include Grant Park and the Wild Hare. I was inspired to go to Chicago because of this movie. I wanted to recreate all the moments Darius and Nina shared together. This has been one of my travel goals for years and it would finally happen. One Saturday when I was sick of dreaming, I booked my ticket for the memorial weekend. I would bring my professional camera with me to channel Nina and my mac computer to channel Darius. It would be the perfect infusion of what I love to do write and take pictures for a whole weekend.

A Love Jones Lover Bucket List

The Sanctuary

The Spoken Word Lounge, 1200 W 35th St., Chicago, IL 60609

The Sanctuary is a cool-cat nightclub where the hottest poets in town share their spoken words and deep thoughts. The smoked-filled room makes for the perfect introduction into the poetic mind of Darius Lovehall as he shares with the audience his “Blues for Nina.” Unfortunately, the Sanctuary is just an illusion and doesn’t actually exist. But there’s a huge spoken-word scene in Chicago.

The Wild Hare

2610 N. Halsted St., Chicago, IL 60614

Darius and Nina’s first date went down here. The Wild Hare is a Caribbean-inspired bar lounge located in the Lincoln Park section of Chicago. It’s particularly popular because of the live music that starts every night at 9PM. There’s a diverse crowd, from athletes wanting to enjoy an ice-cold Red Stripe to lovers conversing in the dimly lit corners of the venue. The walls are adorned with bright yellow, green and red hues and flags hanging from the ceiling. You can’t go wrong with the jerk chicken platter and a side of Jamaican beef patties. The Wild Hare’s mouthwatering menu is only enhanced by the sweet sounds of Bob Marley blasting through the speakers.

The Buckingham Fountain

301 S. Columbus Dr., Chicago, IL 60605

The lighting of the Buckingham Fountain is perfect for a romantic smooch. The fountain spouts every day from 8AM-11PM, but contrary to popular belief, it’s not named after the palace in London.

A Bookstore

Myopic Books 1564 N Milwaukee Ave., Chicago, IL 60622

The scene of the crime… Darius is caught with another woman amongst the books here at one of Chicago’s oldest and largest used bookstores in the heart of Wicker Park. Definitely not a high point in the movie, but dramatic!

Museum of Contemporary Photography (MoCP)

600 S. Michigan Ave., Chicago, IL 60605

While the location isn’t featured in the movie, the essence of photography is peppered throughout, which makes MoCP well worth a visit. Although the museum change exhibits about five times a year, the current exhibition, Dandy Lion: (Re) Articulating Black Masculine Identity, is a must-see. The photographs in this exhibit are reminiscent of Nina’s work (if she really existed).

Chicago Stepping Class

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Darius and Nina showed off their chemistry while on the dance floor. If you’ve never heard of stepping or you’re just intrigued by the art, consider taking a beginner’s steppers class while in Chicago. Classes are $10-$15, but you won’t be disappointed.

Black Stone Hotel

636 South Michigan Ave. (lobby entrance on East Balbo Avenue), Chicago, IL 60605

The Black Stone Hotel has definitely been upgraded since the filming of the movie but still has its original charm. Go for a drink at the bar and see if you can snag a peek into the very room where the Annual Steppers Ball took place.

Chill along the shores of Lake Michigan

63rd Street Beach 6300 S. Lake Shore Dr., Chicago, Illinois 60649

“You only get one true love… two tops.” Lake Shore Drive is the perfect spot to take in Chicago. Take a walk, think about the one that got away and how to get them back.

Love Jones

My First Experience as a Solo Traveler

Alone. Not by choice. My boyfriend (at the time, we are no longer together) and I got into an argument. We parted ways that weekend. I was on my own in a huge city much like my own, but it was not NYC, it was different and I would be doing a disservice to Chicago if I compared the two.

Alone. I never anticipated Chicago being a trip for one but God always has other plans for us, doesn’t he? After settling in my new hotel, I decided to wear my hair in its natural state to represent the sudden burst of freedom I now felt. It was liberating to say the least. The first thing I did was explore the Magnificent Mile. I walked outside of my hotel, conveniently placed on the corner of Ohio and Mag Mile and proceeded down the strip admiring the tall buildings and the shopping. I was in Chicago for sure. There were stores for days—Louis Vuitton, Chanel, Guess, Ralph Lauren, Under Armour, Neiman Marcus, H&M and the list goes on. I decided to take a boat tour of Chicago along Lake Michigan followed by a trip to “The Bean.” I looked around at all the people swarming towards the bean with their families and friends and at that moment I wished I could share this time with someone—but I couldn’t so I did what anyone else in my situation would do…I found someone who had a nice and friendly demeanor and asked if they could take a picture of me—I was alone in Chicago, but that didn’t take away from the fact that I was still a tourist. I met two middle-aged women who were more than happy to take my picture. They complimented me on my natural hair, in awe of what I did to make it look the way it did and went on about their day. I felt exhilarated. My fear of being alone in Chicago wasn’t completely gone, but I loosened up. I would make the best of this trip and enjoy the wonders of solo travel.

The next morning, I woke up and had time to reflect. I sat in silence. I prayed. I talked to God. I was able to write. I planned out my itinerary. I talked on the phone. I did everything I wanted to do in MY time. I planned to do a museum day. I would visit all the museums in Chicago that were on my itinerary. Three museums in one day. As a matter of fact, three museums in five hours, since I didn’t get to my first museum (The Art Institute of Chicago) until noon and everything closed at 5PM. I say this all to say, I was on my own time. I didn’t have to answer to anyone else but me. I was accountable for how my trip would go. This was the day that my fear of being solo in Chicago completely left me. I no longer feared someone would notice I was alone, or that I would be kidnapped. I let go of everything and lived life. I enjoyed my time walking through the exhibits of the Art Institute, interpreting art from my perspective and not the perspectives of others. I enjoyed taking pictures of pictures at the Museum of Contemporary Photography and watching the Dandy Lion video over and over again without being rushed by someone else. I loved learning about the history of African Americans at the DuSable Museum and getting caught in the rain, looking for the bus on the way back to the hotel. It was beautiful. It was liberating. It was such a necessary experience to push me out of my element. That night, I decided to take myself to a nice dinner. I wanted to visit the Wild Hare with my ex. boyfriend and dance the night away to reggae music, but things did not turn out as such—so guess what, I visited without him. I arrived at the dinner around 7:30PM and I was surrounded by other couples on date night but that didn’t faze me. I asked the hostess for a table for one and ordered my jerk chicken plate filled with cabbage and rice and peas. I had an ice-cold drink to go with my dinner and danced for a few hours to old school reggae music. When it was getting late, I took a cab home and got back to my hotel around 11PM. The next morning I took the CTA Blue Line train and found my way back to the airport. Overall, it was such a beautiful trip.

My first time as a solo traveler was an experience. I am not going to act like it wasn’t scary because it was. I don’t like being alone, especially in a hotel room by myself but now, I understand that this time alone was exactly what I needed. I had time just to spend with myself. I had time to think and evaluate my life decisions. I was surprised by my own strength because I could’ve just remained in the room, stagnant since I was alone, but instead, I was empowered. I got up and did everything that was on my itinerary. I am now more open to an experience like this.

Ky Tip: 10 Tips to Conquer Solo Travel as a Woman

  1. Be Bold: Do not be afraid of conquering the city you are visiting. Make sure you know everything you want to get done and go for it.
  2. Prepare: Before I started each day, I had an idea of the things I wanted to do and how I would do it. I also googled what time everything opened and closed, and planned my daily itinerary based on my research.
  3. Don’t be afraid to ask questions, directions or someone to take a picture of you: Just make sure who you ask makes you feel comfortable.
  4. Try to get home at a decent time: I wouldn’t advise staying out until the wee hours of the night especially as a woman traveler. Safety First!
  5. Treat this new city like it’s your own and you deserve to be there: My friend gave me the advice to act like I was out and about in NYC and once she said that, my whole mindset about the trip changed. I wouldn’t be so cautious in NYC so why should I be afraid in Chicago?
  6. Enjoy time with you: Take time to breathe, read or even sit in silence when you’re on your solo trip.
  7. Don’t be embarrassed to have breakfast, lunch, or dinner by yourself: Again be confident. You may get stares, which is expected, but people will ultimately respect your independence. However, it’s okay if you just want to take your food back to the hotel. #NoPressure.
  8. Meet Up: If you’re going to a new city solo, see if your friends or family know of anyone you can connect with or if there are any events or meet up groups happening.
  9. Treat Yourself: Maybe it’s a cupcake or a new outfit but make yourself feel special…you deserve it.
  10. Little White Lie: Never tell someone you are alone. Safety First!

Chicago Travelbyky

Are you ready for a Baecation?

You think you know, but you have no idea.

That tagline will forever be in my head. As a kid, I spent hours upon hours watching the Real World on MTV. There was something so genius about putting a group of young, eccentric people in a house together and discovering who they really were at their core. Spend enough time with someone and their inner selves will begin to show. Whether it’s their passions, vulnerabilities or insecurities, it all begins to spill out. I can now say the same thing about going on vacation with a mate. If you really want to know your boyfriend/girlfriend go on vacation with them. What makes a baecation different from just hanging out at the house or in your neighborhood together is that both of you are completely out of your element. You will begin to notice things about how the person you’re with takes charge (or not). You’re more inclined to notice things like if your boyfriend will instinctually help you with your bags or if your girlfriend will make you breakfast in bed. Things that you didn’t know you were seeking might be revealed. Which can be a good thing or a bad thing.

I say this from experience. I took my first baecation recently and what was supposed to be an amazing opportunity to explore a new city that we both have never visited ended with the demise of our relationship.

Discretion: I am not writing this piece from a place of bitterness, more of a cautionary tale.

My relationship was not ready for this next step of traveling together. There were a lot of loose ends that needed to be tied and a lot of things that we both didn’t know or like about each other when we went away. When I am on vacation, I hate taking naps as soon as I get into the room. However, he wanted a nap, which turned into 6-wasted hours of a day. It gave me anxiety watching him sleep when I wanted to discover this new city; we had a whole itinerary planned and each hour that passed made me feel like we would get nothing done. Yet what he didn’t know is that I go to sleep really early so by 10PM I was turned down and this was prime time for him to turn up. He wanted to hit up a blues club around 11pm but by that time you could hear my snoring miles away. Our personality disparities were shown in many other ways and we ultimately realized this relationship wouldn’t work.

Before you decide to take a baecation with your mate you must have a discussion, and in this discussion be totally honest about your expectations for the trip:

  • How will we pay for the trip? Do you have a partner that will take care of all the costs? Sometimes as women we would love this, but it’s not always realistic for us working-class people. So to be fair you both will most likely be splitting the cost. Who will pay for flights? Who will pay for hotels? Or will you just go 50/50 on everything?
  • How will we pay for things while on the trip? I harbored a little resentment when we were on the trip and my boyfriend didn’t pay for certain things. It bothered me when we went to dinner and I had to pay half or when we went to an attraction and I had to pay for my ticket in front of the lady at the stand (who I secretly thought was judging me). Yes, I am petty (maybe a bit unrealistic) but these were my concerns.
  • Manage Expectations, What do you both want to do during the course of the trip and how can you compromise and get everything done so everyone is happy? Brainstorm all the things you would like to do and draft an itinerary.
  • How will we get to the airport? Together? Apart? When I went away with my now ex-boyfriend I was a little annoyed that he didn’t come to pick me up and we just go to the airport together. Granted he lives in Harlem and I live in Brooklyn (two different worlds) but it was 3 AM and I am a female in a taxi cab by myself. I’ll admit it was scary but I got to the airport safely. What I would’ve preferred was for us to go together. Again, maybe you are not as particular.
  • Are you a stay-on-the resort person or do you like to vacation like a local This is important! You both have to make sure you’re on the same page. If one person wants to explore and the other wants to hang out by the pool all day you won’t be spending much time with each other.

My best advice is to keep the peace, ignore little idiosyncrasies and live in the moment, at least until the vacation is over.

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