Back in October we traveled to Chicago for some work stuff and whenever we travel for work we always make time to be a tourist. When we left for Chicago it was right when Southern California was getting hit with 100+ degree weather so we were pretty excited to step out of the airport and be greeted by gray skies and rain. Being there right before Halloween there were pumpkins and cobweb decorations everywhere. But the city was also prepping for the beginning of Christmas and we actually got to see the Macy’s store window displays, some all done and a few still being worked on. I mean, that might’ve just been the highlight of our trip.

Whenever we’re in a new city I always try to imagine ourselves living there, to see if that city is calling our name. Florence, Italy did (hopefully one day we can for a few months!), while Portland is still #1 on our list to move to. I didn’t think Chicago would but maybe it was the perfectly chilly weather or the neighborhood we were in — at the end of the first day walking around, we looked up places for rent out of curiosity. We stayed in an Airbnb in Old Town, it was 3 stories and every morning I’d walk towards the window overlooking the street, watching people off to their morning commute towards the train station, bundled up in jackets and a hat, with their heads down avoiding the cold wind on their faces.

New places are always interesting. We love just walking around. Not always doing and seeing all the tourist stuff but definitely looking like one taking photos of everything. Here are a few we took around the city. Oh! And whenever we travel somewhere people sometimes ask us for recommendations on where to eat or what have you. Our answers are usually lame but this time we can actually share some! But you have to scroll through our photos to first.

lou malnati's chicago chicago subway chicago subway lincoln park chicago in the fall lincoln park zoo tigers chicago bean pumpkin landscaping in chicago

Places to eat in Chicago. And two free places to visit.

+ Alright first up, the big debate in Chicago: pizzas. We’re not much of deep dish pizza people but for some reason we were all about eating some while we were there. Afterwards we were told we should have tried regular pizza because apparently that’s where it’s really at but we actually had a lot of fun trying out the two big pizza places and seeing which deep dish we liked better. Lou Malnati’s versus Giordano’s. Our pick: Lou Malnati’s. But hey we recommend trying both and deciding yourself which one you like better!

+ The Chicago Diner. This is for our vegan peeps! This place is yum. We definitely recommend ordering the poutine appetizer (waffle style fries with vegan cheese and gravy). The serving is huge so sharing is recommended, we were stuffed after just that and then our actual meals came out.

+ Chicago Bagel Authority. If you’re looking for that authentic bagel eats. We’re not much for bagels but again, something came over us and we ate and enjoyed.

+ Kanela Breakfast Club. This was in Old Town and it’s a cute breakfast place. We got there early before the Sunday brunch rush came so we were able to be seated right away. We splurged and ordered the monkey bread which was a yummy sweet treat.

+ Eva’s Cafe. Another place in Old Town but smaller than Kanela and it felt more like a locals’ spot which we enjoyed. Perfect for coffee and they also have little breakfast sandwiches or treats.

+ Lincoln Park Zoo. It’s free to walk around and we spent a good time watching the monkeys and the lions…which were just chilling on rocks in open air (photo of them above).

+ Lincoln Park Conservatory. This was the perfect place to walk around in and warm up a bit. It’s a greenhouse so it warms you up perfectly ha. Just be careful going back out in the cold afterwards.