Chicago in 500(ish) Words

Disclaimer #1: I call my city reviews “500ish” words because I’m trying really hard to be consice… but anyone who knows me knows that I’m not exactly short with my words.  So this is really about 750.  Enjoy.

Disclaimer #2: I reeeeeeealllly want to be one of those people who carries their DSLR camera around and takes stunning photos of their surroundings while exploring a new place, so I always pack it when I go on vacation.  But then it never leaves the hotel room because a) I hate feeling like a tourist (even though I’m the utlimate-let’s-take-a-million-slefies-in-the-bean-tourist. b) Lugging it around is a pain and gets in the way of adventures like boating and biking. c) Since I never bothered reading the manual I barely know how to use it and therefore my photos never turn out that great so while traveling I usually stick to my iphone.  If you follow me on instagram, I apologize because you’ve probably already seen a ton of these photos because I was instagraming like a maniac.

Now on with the trip!!

24 hours before leaving for Chicago, Pam and I realized we had a problem.  We had no plans.  Like none whatsoever.  So I sent out a cry for help on facebook, and boy oh boy did our friends come through with a whole slew of great suggestions!


Thursday we rolled into town and met at our hotel: The Wyndham Grand Riverfront.  Killer views of the city and just a mile from the starting line of the marathon, this was the perfect place to call “home” for the next 4 days.


A day of travel deserves a super comforting dinner.  How bout big, steaming bowls of Pork Belly Caldo at XOCO, one of celebrity chef Rick Bayless’ signature restaurants.  (PS it lived up to the hype!)


Dinner wouldn’t be complete without some sweets, so dessert came in the form of peanut butter cup donuts from Firecakes.


What better way to discover Chicago than from the 96th floor of the Hancock Building.  The cocktails in the Signature Room were average, but the view was worth the 16 bucks.


I’m not sure if the perfect day exists, but Friday was pretty darn close.  After sleeping in a bit, we started our day with a run along Lake Michigan.


Brunch is a mandatory part of exploring a new city and Yolk on the near north side was the perfect choice.


Next was a $7 day pass to rent Divvy Bikes, and a ride down the coast to the Marathon Expo.


At the Expo we picked up our race bibs and bought some overpriced but super cute official Chicago Marathon gear.


Then it was time to Divvy Bike back to Navy Pier for our 4:15 Architectural River Tour with Sea Dog Tours.


Our guide Brian Vance was crazy good, full of knowledge of his city and always quick to crack a joke.  The views of downtown from Lake Michigan were out of this world!


After our tour we ventured out to Lincoln Park, a residential neighborhood, to check out some local  joints recommended by friends.


We started with  Thai food at Pot of Noodles where Pam wow’d the server with her ability to eat the “as spicy as you can make it” Pad See Ew.


Next stop was Molly’s Cupcakes for dessert and Barrelhouse Flats for cocktails.  They have to be some of the best in the city!


Saturday we took it easy and started off the day with Brunch at the Bongo Room in the South Loop.


While we waited  for a table we hopped back on our Divvy Bikes and scouted out the marathon course.


After brunch we paid a visit to the iconic Bean before returning to the room to rest up a bit, knowing we had 26.2 miles to run the following day.


Prerace dinner was at MityNice followed by some last minute fuel in the form of Ghirardelli ice cream cones.


Sunday morning was up before the sun to make our way to Grant Park for the start of the marathon.


It wasn’t a personal best for either of us, but we both agreed that we had an absolute blast running 26.2 miles around Chicago, and that the city put on a phenomenal marathon.


I enjoyed a local brew and beautiful view of the city while I waited for Pam to finish.


We kept our tradition of post-race burgers alive by stopping at Edzo’s Burgers in Lincoln Park.  The staff couldn’t have been friendlier (high fiving us when they heard we ran the race) and the food was a-maze-ing.


Naps ensued.

Then it was off to meet Pam’s friends for drinks and snacks at the Dry Hop in Lakeview.  The first round was free for runners!


We went to bed exhausted but elated.


Monday morning was started with one more run along the lake before packing up the room and checking out of the hotel.


Then it was off to lunch at Gino’s East for Chicago style deep dish pizza.  Can you even think of a better way to end a trip??


The only bad part of vacationing with your best friend is saying goodbye.  After pizza we parted ways at the subway station before catching trains to our respective airports (O’hare – her, Midway – me).


All I can say is Well Done Chicago, well done.  I like your race, your people, and your town very much. Can’t wait to return again!!



Tall  One

PS: Interested in any of the places I mentioned above?  The majority were recommendations from friends, but a few we discovered on YELP.  Links are below.


2 thoughts on “Chicago in 500(ish) Words

  1. What a nice write up of my city! I *love* Edzo’s, I live closer to the original up in Evanston. Xoco is great–and you know his Tortas Frontera restaurants at O’Hare (there’s two) are very much like the sandwiches at Xoco, next time you find yourself at that airport.

    For pizza, I don’t really care for deep dish but there is a second Chicago style pizza that most people outside of Chicago don’t know about (I didn’t!)–thin crust, cut in squares. The catch is you can’t really get a good one close to downtown that I know of. The best bets that I can think of are Vito and Nick’s at 84th and Pulaski, Candlelite at Western and Howard, Phil’s at 35th near Racine, Marie’s at Lawrence and Pulaski.

    1. Thanks for stopping by the blog! Such great suggestions. I loved Loved LOVED Chicago and can’t wait to visit again. I’m super intrigued by this square pizza, it seems like reason enough to plan another trip!

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