A City Guide: Insider Tips For Perfect Trip To Chicago

Morning

It was a Saturday morning in Logan Square and what better way to start off your day, than having brunch at Longman & Eagle. You can read all about our brunch here. If you can’t get into Longman & Eagle, you can try eating over at Lula Cafe, which is a fabulous “farm to table” restaurant in Logan Square. You can’t go wrong with either of these choices.

Afternoon

You can spend a whole day walking around Logan Square and check out all the great shops on Milwaukee Ave. Or you can do what we did, which was take the Diversey Bus down to Lincoln Park and walk along the coast of Lake Michigan. It was a lovely summer day at the lake and so many people were out enjoying the water. The heat was starting to warm us up, so we decided to dip our toes in the water – very refreshing!

After the park, we decided to checkout Old Town for a bit. There are some great shops on Wells St. between North Ave. and Division St. We ended up getting some wine from Chicago’s oldest and finest wine shop, The House of Glunz. They were doing a free wine tasting, so we were able to try a few different wines before making our selection.

After Glunz, we decided to head back to Logan Square and chill out before dinner. We took the Division bus down to the Ashland Ave. stop and walked up Milwaukee Ave. We didn’t realize until we got there that Wickerpark Fest was going on. These festivals happen in different neighborhoods almost every weekend in the summer. Pilson and Chinatown had similar festivals going on the same weekend. We stopped at a few booths and stores on our way up Milwaukee. We got back to my friend’s house and relaxed until dinner time.

Evening

After a few hours of chillin, we strolled over to Daisies to have ourselves a pasta feast. If you aren’t aware of Daisies, it is a vegetable-focused and pasta-driven restaurant, which you can read about here ☺️

If you are planning on going to Daisies, I would recommend getting a reservation as early as possible. We showed up at 5pm when they open for dinner service and were only able to get bar seats. Still worth it IMHO.

After that amazing meal, we mozied back to my friends place and played Mario Party for a few hours. The Perfect Evening??? YES!

Day Two

Morning

Sunday mornings in Logan Square are best spent at the Farmers’ Market on Kedzie Blvd. It starts right across the street from Lula Cafe – which would be a great place to grab brunch before strolling through the market.

Before checking out the Farmers’ Market, we stopped at 4LW for some coffee. Great coffee and great people.We then walked through the Farmers’ Market. It actually bigger and in a different location than it used to be. We didn’t buy anything this time but there is a lot to choose from. Lots of fresh vegetables from local farms and also a lot of prepared food stands as well.

We continued down Kedzie after the Farmers’ Market and walked through Palmer’s Square. It really is so nice walking down the boulevard. For those of you that don’t know, Chicago has park lined boulevards that connect a few of the big parks. The main traffic is in the middle with four lanes, then parks on both sides that go about a 100 feet, then another street for parking. Such a beautiful feature of the city!

Afternoon

Ok, so I have a confession to tell you all…… I’m a tacoholic! I love tacos with all my heart and I don’t care who knows it! My favorite place to get tacos in the area is called Traspasada in Avondale.

They are famous for their black salsa, and not to make a big deal or anything, but I would eat my hands if they were covered in that salsa! It’s delicious! Also, the horchata is simply divine! I’ve tried all their tacos in the past but my favorite is the al pastor. Chips with black salsa and soup comes out automatically when you sit down, then I usually order 3 al pastor tacos and horchata. If you go, I recommend the same order!

From the outside, Traspasada doesn’t look like much but don’t be deceived. THIS PLACE SLAPS!

And if you are looking for a place to have a beer afterwards, The Beer Temple is right across the street. It’s a bar on one side and a beer shop on the other. Great place with lots of varieties to choose from.

Evening

I’m gonna be honest, by Sunday night, we were all feeling a bit tired and just wanted to chill. We ordered in Indian food from Cumin in Wicker Park. Their chicken korma is phenomenal. We ordered a bunch of dished that night. I don’t recall them all but I remember it being delicious!

After that, we just chilled and watched the olympics.

Day Three

Morning

This particular Monday morning it was raining and I was looking for a place to chill for a little bit. I popped into New Wave Coffee, which is a great place to get coffee, sit, relax and do some work if you would like. There are plenty of seating options from couches to tables with chairs. It does get busy during the day, but this morning was pretty chill. I had a matcha latte and hung out for about an hour or so.

My caffeine fix still was not sufficed, so I took the blue line down to the Western station and walked to a great Dark Matter Coffee shop called Electric Mud. I got myself some kind of spicy latte that was delicious.

Afternoon

I was starting to get hungry and yes… again I was in the mood for tacos! This time I stopped by Big Star in Wickerpark. Usually pretty packed at nights and weekends, I got lucky and the place was empty. I sat outside, and had myself 2 tacos – Al Pastor and Camarones Fritos. Very delicious! Quick shlay and I kept it moving.

After that, I went back to the apartment to chill for a bit and wait for my friends to be done with work. We had plans to meet up with other friends at a restaurant for dinner.

Evening

This was another fantastic meal at a great restaurant in Bucktown called Chef’s Special Cocktail Bar. This wasn’t open yet when I still lived here but I believe it’s been open for a couple years now. It’s a take on American style Chinese food but taken to a seriously elevated level. I trust my friends’ judgement so I let them order all the food and everything comes out family style – my favorite!

Everything was so delicious but some of the best starters for me were the smashed cucumbers and egg rolls. These egg rolls might have been the best I ever had – perfectly crispy on the outside and soft delicious filling on the inside. The dan dan noodles with ground pork was super good with a nice kick, but I think my favorite dish was the twice cooked pork. That pork belly was stupid delicious.

I honestly forget everything else we ordered because it was all coming so fast, and everything worked well combined on my plate. This one really hit the spot for me!

Day Four

Morning

This morning I did an activity that is not only extremely touristy but loved by the locals of Chicago as well. I took the Chicago River Architecture Boat Tour! The Chicago River is lined with world class architecture and it’s so cool to see it all from the river’s view.

There are a bunch of tours you can do but I would say the most popular one is the architecture tour. You have two options – you can go through Wendella or through the Chicago Architecture Foundation. Wendella is a bit cheaper but the Chicago Architecture Foundation tour is supposed to be slightly more informational. I have taken both over the years and they are both great.

This particular time I was doing the tour with the Chicago Architecture Foundation and it was a great tour. It was hot that day, so when the boat goes under the bridges, you get a nice cool breeze. Luckily there are a lot of bridges! The tour goes down the east branch towards Wolf’s Point, then turns right to go up the north branch of the Chicago River. The history of the buildings is so interesting – different industries have come and gone through this area so the buildings have been repurposed. And it’s so cool seeing the blend of old and new architecture styles.

The tour continues down the south branch to about near the old Post Office and then we start heading back to the dock. Another successful Architecture Boat Tour in the books!

Afternoon

After the boat ride, I went for a nice long walk along the lake and through the parks – Maggie Daly Park and Millennium Park. I used to work right across the street from these parks so it was nice to be back to where I would hangout on my lunch breaks.

The Bean is still super kewl