Chicago: The Windy City

I can’t believe it either, before this past August, I had never been to Chicago before in my life! I loved the movie/play, and one of my favorite bands, Filligar, is from Chicago, but I had never seen the Windy City for myself. That is, until one of my best friends moved there last June for a new job and I thought: yes! This is my chance!

Photo Courtesy of:

I went to visit Rachel the first weekend in August, which was perfect timing since this was also during the famed music festival, Lollapalooza. Even though this was during a busy weekend, with the help of the Matrix website, I found round-trip, non-stop flights from Syracuse to Chicago O’Hare (one of the busiest airports in the States,) for $300. It’s definitely not my best deal, since I found non-stop round-trip flights from White Plains to DC for $100, but still very good considering the weekend and major city.

Chicago from Above! Photo Courtesy of:

What matters to me most about booking flights is the flight times and prices. If I’m going for a short weekend trip with not a lot of time to be able to catch up on sleep, 5 or 6AM flights won’t cut it for me. I found a flight that left Syracuse at 3pm and got into Chicago at 5pm, which was perfect since Rachel was working that day. My departing flight was at 4pm and got into Syracuse at 6pm. So, even though I could have taken one of those early morning flights, I made up for it by being able to spend most of the day in Chicago.

Chicago Neighborhoods

The entire weekend was beautiful and hot. I arrived into O’Hare, caught a cab, and made my way over to Rachel’s apartment, which, by the way, is located in an adorable neighborhood, across the street from where GreenCity Market (the farmer’s market) sets up, and few blocks from the lake, beach, and fantastic shopping along Michigan Avenue. We caught up when I first got in and then got ready for dinner and drinks with her Chicago friends.

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If you’re in the mood for some delectable and mouth-watering tapas, make your way over to Mercadito. They have a great drink menu, and their guacamole was fresh and delicious. I can’t remember the tapas we got, but I do remember that they were fantastic. One great thing about Mercadito is that on the weekends, they serve midnight brunch!!! I love brunch, and I love breakfast foods after midnight. YUM. We later went out for drinks at a new rooftop bar, The Terrace, at the Hilton Hotel. It was a balmy night, so being outside in the lounge-y area with views of the lake and city was a recipe for a perfect night! The roof was strung with big bulb lights, and the seating area was a mix of low lounge couches and high top tables, perfect for mingling.

The Terrace

Saturday morning we walked across the street to GreenCity Market for some breakfast. Oh my god. If you ever get a chance to go there, make your way over to the homemade crepe station and get the fresh berry crepes. I still dream of them. We walked around seeing all of the things the market had to offer, from fresh flowers, to vegetables, to handmade jewelry. As if you didn’t know from my previous posts, I love farmer’s markets. We kept walking along Lake Shore Drive along the lake and beach (where we also entered contests for a fashion blogger. She photographed us in our outfits and readers of her blog voted on who had the cutest outfit. I won second place and a $50 gift card to!) We shopped along Michigan Avenue and the mall, and stopped into the retro Hershey’s store for some souvenirs for my family.

Green City Market, Lake Shore Drive, & Michigan Avenue

Later that night, Rachel took me out for my belated birthday dinner to the Paris Club. The Paris Club is a swanky, beautiful, and trendy restaurant that is pretty hard to get into. I loved everything about it. Despite being hard to get into, the servers were not pretentious, but very helpful, the atmosphere of the restaurant was cozy and vibrant all at the same time, and their playlist was excellent. They played everything from Foster the People to the Naked and Famous. My kind of music!

Rachel and I

Our dinner was amazing. From the pretzel croissants to start, to the French 59 drinks (go make them, you’re lucky I just gave you that recipe) to the scallops, everything was perfect. After a few more French 59’s we headed out. After all, we decided to get up early Sunday morning for some yoga! Thanks to Lollapalooza, we were able to attend a free popup yoga session (which, by the way, was one of the best yoga classes I’ve ever taken. I was so sore the next day, but it felt SO good.) We finished our yoga class, and feeling great, promptly went to brunch at the Bongo Room.

The Bongo Room’s AMAZING Restaurant

The Bongo Room is another place I dream about frequently. Do you know how ridiculously amazing their menu is?! We had a hard time figuring out what we wanted to order, but finally decided on the strawberry banana pancakes and red velvet pancakes. BEST. EVER. We walked around exploring Chicago a little bit more, and then it was time for me to head back to the airport.

Lollapalooza Perks & The Bongo Room Brunch!

After another great weekend trip, I had a hard time leaving. Chicago is unlike any city I’ve been to. I love that it’s still a big city, but at the same time, everything seems inviting and welcoming. I loved everything about Chicago. It wasn’t like NYC where a lot of the buildings look the same. Here, each building has its own personality and character, and the city is filled with beautiful parks. Another plus: it’s on a lake. With a beach. So basically, you get a fun, friendly, big city all on the water for some great scenery. What more could you ask for?!

Chicago at a Glance

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