I think I am on my 15 or so trip to Chicago, I know it’s over 10 and under 20 times. Each time I go I try to seek out new places to eat, stay, and shop. Some of my trips are planned way ahead of times some are just on a whim. I scan the Southwest app for great deals weekly. Cliff is a frequent flier of Southwest so I fly for free when he flies on his companion pass.. it makes travel less expensive. This flight cost us $22 roundtrip I was free and he used points! Next was to find an inexpensive hotel. We usually Airbnb when we can because we like staying in neighborhoods, but Cliff found a hotel deal we couldn’t pass up.
FieldHouse Jones was the choice for this trip. They had me at great graphics and eye-catching photography of the hotel. They had Cliff at the whole sport like themed decor of the place. The pictures on their website we exactly what it looked like in person. I was sold.





Not to mention the AMAZING coffee shop in the lobby, DropShop Coffee. It really is perfect. You will have to get a cup of coffee and walk around for yourself and explore the hotel. Better yet order some lunch from DropShop and sit in the open air area by the lobby… I was dying to just sit there and relax but I didn’t have time to this trip.
We took an early flight out of LAX (mind you we never fly out of LAX but we could not refuse the price) and landed at Midway in Chicago at 11:30. I love flying into Midway because you can hop on the train (Orange Line) straight from the airport into the city. We took the Orange line to the Brown Line and were at our stop in 25 minutes… walked off the train and immediately saw a Starbucks and a Paper Source… I was already in love.
First on the list after checking in and even before lunch was Cliff’s beloved Field Notes. Cliff started collecting these notepads and using them long before I discovered them. Something we both appreciate is a good notebook since we are always taking notes, writing stuff down or working. I was just in Chicago a few weeks ago and wasn’t able to come by here but still managed to buy about $40 worth of stuff. This trip I think I bought the same amount. Worth every penny.



What did I purchase? A planner!! And a Portland set of notebooks, Cliff bought some new pens, The green book on baseball, and pens, (the coffee one we actually bought at the Starbucks Reserve at Wrigley Field). He gave us the Chicago flag ones (I just bought those ones last week LOL) and some rubber bands to keep the notebooks together.
Now it was onto lunch.. I was starved! Cliff had his list of must eat at places so we were off to Logan Square to Bang Bang Pie & Biscuits.



It was perfect! Every single bite! This is now going to be a regular stop on our Chicago trips. Did you see that crust on my pot pie??
Ok now for some more shopping. I had a few places on my list. Steel Petal Press was our second stop of the day. If you follow my Instagram stories I walked you through this store. It was cute! Love seeing the actual printing press right in the store. Bought a few things that I loved for me.. and some gifts as well.

We walked through Logans Square into a few more shops. Play was a one of a kind toy store. I wish we had more of them. If you followed my Instagram story you saw the CD’s of Emeniem, Rhianna, Prince, Bruce Springsteen, and more sung to lullabies. I should have bought them all! I managed to pick up a few unique items as gifts for the holidays.. they even gift wrapped them for me. Love that kind of customer service, so glad we have establishments like that still going strong.

Explored Loagn’s Square and parts of Bucktown… still more to these neighborhoods we just ran out of time. I think we walked close to 6 miles exploring… and we were not stopping now. I was craving Greek food for dinner. Another 2 mile walk from where we were and we were in Greek Town!
Cliff had not walked this route before so it was great scenery. We deserved every bite of whatever we were going to eat after that trek! My go to restaurant in Greek Town is Greek Islands. My uncle took me there a few years ago and it has slowly become of my favorite restaurants ever! One of my first trips to Chicago my uncle took me to Greek Town and we ate at Athena. I have not been back since then so Cliff suggested we try it again. It was no Greek Islands but the plate we shared was delicious! We ordered Saganaki (the flaming cheese I always Instagram about!) Its my favorite and we decided on seafood so we split an order of Shrimp Skordati. No pictures… we were just two people at dinner that night. Believe me it was delicious!
We were done for the night! Headed back and were getting ready for the next day!
Cliff picked the breakfast spot again… he’s getting better than I am. It was Batter and Berries. It was voted one of the top 10 best breakfast places in Chicago, so we basically were sold. I didn’t stray off far from what I would normally get.. Banana Nut Waffle. The butter that you see in the picture on top of my waffle was a maple sugar butter so you needed no syrup! Cliff was adventurous and order one of the daily specials, Cajun blacked salmon eggs benedict with cheesy crusted hash browns. His was so savory, they both were a big thumbs up for us!
On to more shops that were on my list! Foursided was just under a mile away.. an easy walk on any given day… but it started raining on us! It was well worth getting wet for. We spent a long time in there and almost $100! I can’t wait to come back and shop some more!

We had time for Cliff to drop into his Chicago office.. we haven’t really been in the city yet, we have stayed on the outskirts this whole time. The office was in the perfect location on the water.



After touring his office we walked a couple blocks to the Goddess and the Baker. Remember the picture of the rainbow cake from my Instagram? It’s from this place. What did I order this time? goddess “almond joy” frappe: liquid chocolate, coconut cream, almond syrup, milk and espresso, blended. topped with whip, chocolate and toasted coconut flakes. It was good!
Now onto the highlight of the trip… The Cubs Game!!!








We hoped on the red line and it took us back to our hotel after a little walk.
The next day we were flying out so we had to be quick in what we had plans for. First off is to find a food truck I follow and get the sandwich I drool over looking at each week. After walking over 1.5 miles out of the way we find them. The Corner Farmacy. They have this one turkey sandwich covered in sprouts!!!! If you know me you know I love sandwiches and sprouts!! Cliff and I shared a sandwich and it was perfect! I have to come back in the fall for the other one I drool over.. it’s an asparagus grilled cheese!!!!! Its seasonal so I will see you in a couple of months again Chicago!
I liked this museum and everything it stands for so much I bought a membership here last year. Anytime I can actively support the arts and sciences I will. The museum of Science and Industry is a full day of science! The Hyde Park neighborhood is spectacular just to explore.
After a day full of science we were ready to eat before we headed out on our flight back home. I got to pick both places to eat at today and I was doing pretty good. So I went for it and picked a ramen place… we are super picky with our ramen so this could go bad real quick. Ramen-san it was. It did not disappoint, and we were very happy people! I ordered the tonkotsu, and Cliff ordered the special for the day, the beef brisket ramen. We are adding Ramen-san to our list of must trys for Chicago. If you follow me on Instagram you saw my story – YUM!

That was our quick trip to Chicago! We spent less than $150 on the airfare and hotel room. Do your research and seek out the less popular hotels. The small boutique hotels are amazing.. give them a try. Or if you want to try an Airbnb you can find some really inexpensive ones! Get out there and travel… to anywhere! Doesn’t matter how you get there… it’s what you do once you land.
happy travels!