I miss everything about Chicago, except January and February

Gary Cole

Just so you know, I (Shy) grew up in the burbs of Chicago, so this city is somewhat familiar…but actually staying in the city just has such a different vibe.


Dwelling $726.50
($100 / day)

Fyi, high cost of food might be a trend. Food is a large part of traveling for us (like it is for majority of folks).


April 13 2019 – April 27 2019
14 Days


We stayed at an Airbnb:


DateNameTypeGoogle Maps
4/13 Portillo’s
Elephant and Castle
Italian beef and hotdogs
Pub / Bar
4/14Andy’s Thai Kitchen
Legend Tasty House
Joy Yee
4/15JJ Thai Street Food
4/16Cooked at bnb
4/17Taqueria Traspasada 2
Fat Rice
Scooters Frozen Custard
Asian / Portuguese
4/18Yuzu SushiJapanese
4/19Black Dogs
Jarlings Custard
Lai Lai Wok
Frozen Custard
4/20Cooked at bnb
4/21Cafe CentralPuerto Rican
4/22Silli Kori
Dona Natys Taco
4/23Cho Sun OkKorean BBQ
4/24Au ChevalBurgers
4/25Cooked at bnb
4/26PortillosItalian beef and hotdogs


Walk around downtown

This city is very walkable and if the whether is nice, holy smokes it has a nice view. Chicago isn’t just the loop but rather about the neighborhoods that surround it, each with its unique characteristics.

More SNOW!

4/14/19 – Snowing outside the bnb

Wouldn’t be the midwest without some snow in April 😉

Day-trip to alma mater (UIUC)

4/19/19 – Train departing Chicago Union Station
4/19/19 – Main Quad at UIUC

Nostalgic seems to be the appropriate word to describe being back here. (Avi has a separate post for Urbana-Champaign with more details). Its funny how your perspective and thoughts change as you grow older and visit a place that had such an immense impact on your life. Obviously both of us had very different experiences here. Avi was, as Elsa from Indiana Jones would say say … “giddy as a school [girl]”. My most memorable times here aren’t about the education or classes, or even the walking around campus, but rather the time I spent with my friends and the relationships built here that contributed to the person I am today. I was going to write more about this journey, but I think Avi has more to say about it than me 😉 … food was still amazing and exactly how i remember, except much more expensive =(.

Walk the Lakeshore trail

4/21/19 – Lakeshore trail in Chicago

Damn … I wish I did this more often. If the weather cooperates, there are several amazing parks and trails around the city but this one tops them all. Walking along this route with the lake on one side and the spectacular Chicago skyline on the other is quite a privilege.


CTA and Uber were our primary modes of transportation. Along with a few friends we knew in town who were kind enough to drive us around occasionally. This city has amazing public transportation.


Chicago is definitely a foodie city! There really is food from all around the world here just like NYC and at a fairly reasonable price. Its very easy to get around with excellent public transportation, food is much cheaper than SF or NYC, and the lakefront is definitely worth a visit. For what you pay, I wished when i lived in Illinois, it was in the city and not the burbs.

We decided to skip the museums, aquariums, etc since we’ve already visited those before, but they are well worth a visit if you’ve never been.