Points North
on Nov 10, 2013 in Travel

Chicago City Lights

As you are well aware from previous posts, the drive from Seattle to Chicago can only be described as LONG. Breathtakingly beautiful at times, and then incredibly flat and mundane at others. So the happy medium I’ve chosen to describe it is “LONG.” Yes, in all caps, because it’s appropriate. I arrived in Chicago after driving through the most dramatic storm, and felt a sigh of relief as well as exhaustion upon pulling up to my destination after dark.



I rented a small apartment in between Wrigleyville and Lakeview. I kept referring to the neighborhood as Lakeview, but some said it was Wrigleyville and then some said Wrigleyville was a sub-neighborhood (is that real?) of Lakeview, so I’ve decided to just say I was in between the two until city planners can prove one way or the other. It was a great location nonetheless, with so much within walking distance it was almost unreal. I was close to the Southport Brown Line and the Addison Red Line stops. I was also close to several bus stops for getting around. Within walking distance was Wrigley Field, several shops, restaurants, bars, and night life activities. I can’t think of a more central location for exploring the Chicago scene.


Although I did research a couple coworking spaces out of Chicago, scheduling conflicts prevented me from making a visit and trying them out for the day. A bulk of my work occurred in my lovely apartment, where I could take a break around lunch time to stroll the neighborhood, and then also take off early to enjoy all that Chicago night life has to offer.



ARCHITECTURAL BOAT TOUR OF CHICAGO: Best to take this tour on a warm day as it can get quite chilly on the water; either that or layer up (and I mean seriously! Layer up!!!). When I asked around as to what’s the one tour I should absolutely do in Chicago, hands down everyone said the Chicago Architectural Boat Tour, put on by the Chicago Architectural Society. See the windy city through a whole new set of eyes, and pick up interesting tidbits of facts and knowledge along the way. It’s also a great tour to have your camera handy, as well as a few dollars for drinks on board.

LINCOLN PARK ZOO: Check out the Lincoln Park Zoo and the Conservatory. Both are FREE which makes them awesome in general, but they are also very well laid out establishments that are beautiful and serene to walk through. I enjoyed the plant life and the wild life all the same. Definitely makes for a great late morning or early afternoon stroll. Both are easily accessible by bus and you can walk back to bustling streets when done for coffee or a bite to eat.

ANDERSONVILLE: I loved this fabulous neighborhood! I wish I had spent more time here honestly. It’s the perfect way to spend a late afternoon into the evening. Start with a cup of coffee, then stroll the shops (so many great ones!) that all over unique, vintage finds and one of a kind art pieces. Then pick from the array of restaurants for dinner and drinks. This neighborhood is also accessible by bus so you can easily get in and get out without having to worry about your car.

SOUTHPORT LANES: A vintage bowling alley less than a block from the Southport Brown Line stop = amazing.

CHICAGO CULTURAL CENTER: This center is located downtown, and usually has a great interactive exhibit occurring (for free) on their second floor. If you’re downtown anyway to sight see or do shopping, make it a point to stop by.

THE SIGNATURE ROOM: This is at the top of the John Hancock building, boasting breathtaking views of the city lights of Chicago. Enjoy a cocktail with a friend as you casually overlook all that Chicago has to offer. Take your camera along.

THE GREEN MILL: A great lounge to listen to live blues and jazz music. With an impressive line up and well positioned seating, this place is sure to be a good time. Be advised, they only accept American Express (which I found quite weird) or cash.

LINCOLN SQUARE: Another sweet neighborhood for walking around and enjoying local establishments. Plenty of local, organic shops, cute cafes and restaurants, as well as small outdoor areas with park benches for relaxing with friends. A great way to spend a late morning or an early afternoon, especially when paired with lunch or coffee from a nearby cafe/restaurant.

THE SECOND CITY: (and UP Comedy Club) You must see a comedy show while you’re in Chicago, and improv is best! I had the opportunity to see two here, with two different groups of people. Order a drink and have a good time. Arriving early is a good way to get your drinks early and guarantee good seats in your section.

MILLENIUM PARK: See the bean, enjoy beautiful views of the city, foundations, and more. A short walk from downtown. If you’re spending a day downtown, I would grab coffee and start with a stroll through here, then enjoy lunch downtown followed by shopping.



Now, I am a more of a health nut, so my choices were definitely on the healthy side, but if you are a foodie, there’s no reason for you to not live it up in Chicago.

Places I went that I loved :

  • bellyQ – delicious eats of all kinds, and nice veggie dishes for me
  • Argo Tea – a sweet tea shop with several locations and the most delicious pumpkin chai
  • Pops for Champagne – downtown, great for drinks and light fare
  • Frasca Pizzeria & Wine Bar – great drinks and eats, and popular so come early!
  • The Chicago Diner – meatless food that your meat-lovin’ friends will still enjoy.
  • Uncommon Ground – nice place for coffee or lunch or to post up with your laptop
  • Adobo Grill – two words: margaritas, guacamole. Need I say more?
  • Kanela Cafe – great brunch spot with veggie options too. Arrive early to avoid the wait
  • Hutch Chicago – sweet place to go for friendly staff, great drinks and eats
  • Cafe Ba Ba Reeba – two words: tapas, sangria. Need I say more?



I didn’t know a soul in Chicago, but as usual that only lasts a couple days. I was able to sync up with someone that I connected with through AirBNB, and she started to point me in the right direction for how to get acquainted with my new surroundings. From there I attended a couple networking events. One that I enjoyed thoroughly was called BLEND; it was a dinner with a unifying topic for conversation, but otherwise attracted attendees from all industries and professions. From here I met a new friend who not only lived in my neighborhood, but literally 2 buildings down! Having just moved back to Chicago herself, she became my social buddy for exploring the neighborhood instantly.

I also attended some tech networking events, and a social gathering for vegans. Both were great opportunities to converse and enjoy the company of new friends, but the BLEND by far gave me the most value.

Additionally, I hung out with my AirBNB host, downtown near her job for lunch, and then also for sangria and tapas before I left (clearly, she knew the way to my heart!). And I also attended The Moth storytelling event, which I’ve been chasing for more than half the year and by far more than half the country! So happy my location and schedule synced up in harmony so that I could attend. I went out with a friend’s sister, whom I had met before when she visited Baltimore. These events are incredibly popular. The host will have you laughing out loud, and the stories will really draw you in. All in all this was a great time.


Chicago is another damn fine city that I really enjoyed living in. Such great people. So easily accessible via public transportation (which I started to really get the hang of, of course as I was headed out the door). I would happily return as often as needed to enjoy all that Chicago has to offer. Truly loved it.





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