My last fun, non-work trip to Chicago was back in 2011. We ate some good food (The Purple Pig, The Gage) and visited almost every museum the city had to offer. However, we stayed downtown and didn’t really venture outside of it, and that was a mistake. 

On this trip we stayed in Wicker Park, limiting our time downtown to an architectural boat tour, and one museum on a rainy morning.  I liked Chicago on my previous visit, but sticking to exploring the neighborhoods this time made me love Chicago. There are so many options for food and things to do, so if you’re planning a trip I implore you to do research and don’t wing it. Many popular restaurants require advanced reservations, so if food is a big part of your trip keep that in mind. 

This guide is a reflection of my 6-day stay, which allowed me to fully immerse in the city. However, even a quick weekend getaway can be packed with exciting experiences if you plan ahead. I hope this guide can assist you in planning your trip, no matter how short or long, and make your Chicago adventure a memorable one. 

coffee shops

Dark Matter Coffee

Neighborhood: Ukrainian Village

Dark Matter has multiple locations, but I visited one on N. Western Ave. Dark Matter was on my must-try list. I ordered off their specialty latte menu and selected the Dolor De Oro Espresso, steamed milk, honey, habanero, cinnamon, and chocolate. It packed a serious punch. Every sip ended with a little burn in the back of my throat. They don’t play!

The only downside to this location is that there was no seating, so you just kind of have to take your coffee and go, which isn’t what we were expecting. So, if you want to chill, I would look into their other locations. 

Barista level friendliness: Moderate

Dayglow Coffee

Neighborhood: South of Logan Square

Dayglow (which also has locations in NYC + LA) was one of my favorite shops. It is a high-end coffee bar where they expertly prepare each drink for you. I've heard their pour-overs are best-in-class, but you know I can't say no to a craft latte, of which they had an extensive menu - I counted fourteen signature drinks! It was tough to choose, and I wish I had an iron stomach so I could have hung out and tried a few. I landed on the Cha Cha, espresso, condensed coconut, oat, and cinnamon.

The space has seating, but only a little, and most of it was taken up by laptop bros.  

Barista-level friendliness: The baristas at Dayglow were a pleasant surprise. In a place where you might expect a more reserved attitude, they are the epitome of friendliness and engagement. Their warm demeanor adds to the welcoming atmosphere of the coffee bar. 

There is little to explore directly near the shop, so this is a destination coffee spot but worth it. 

Prequel Coffee

Neighborhood: Ukrainian Village

This shop was an easy walk from our Wicker Park Airbnb and is on a strip that is worth exploring. The shop was really cute, and there was an added bonus of some random Snoopy and Garfield art. I got the Brown Sugar Cardamom Latte, which was really good; you could taste the flavors, not just espresso and milk. We also got The Breakfast Sandwich—a fluffy egg, juicy pastrami, housemade spicy mayo, and sharp cheddar on a sesame brioche bun. It was an impressive breakfast sandwich.

This is more of a cafe, so there is bar seating, tables, and window seats. 

Barista level friendliness: Very friendly and welcoming.

Wormhole Coffee

Neighborhood: Wicker Park

Wormhole has an entertaining theme of 80s and 90s nostalgia, and even a DeLorean is mounted at the back of the cafe. This is a larger cafe with plenty of seating throughout. Their specialty lattes had some exciting flavor combinations like fresh ginger and curry sauce, and white miso caramel and black sesame. Usually, I’m all for those concoctions, but I went safe with the honey bear. There are really solid lattes here; in fact, we bought a bag of beans to take home. Add it to your coffee list.

Barista level friendliness: Very friendly and welcoming.

Swadesi Cafe

Neighborhood: West Loop Gate

Swadesi is a newer Indian coffee shop in Chicago, and I was so excited to try it. I love authentic chai, and what better place to get it? Unfortunately, it was a letdown. I asked if I could have my masala chai iced (it was very warm, and we were walking), and I was told no without much explanation. I read an online review after the fact saying it’s pre-made, so they can’t alter it, but that means you can’t pour it over ice? So I took it hot, but it was scalding, and once I could even get a sip without destroying my tongue, I really didn’t care for the taste. I’ve gotten pretty good at making fresh chai at home with real spices, so I was surprised it was such a fail. So sadly, I wouldn’t recommend it. 

LOST LARSON

Neighborhood: Wicker Park

Technically a bakery, but also a good spot to stop for coffee. I wish I had more imagery to share, but this was our first stop after landing in Chicago and I scarfed down my chocolate croissant and lavender latte with no regard for social media sharing.

FOOD

KASAMA

I was SO excited to eat at Kasama. However, I would not go through this process again.  

We went on Wednesday, knowing we'd need to get there early if we didn't want to be stuck outside waiting in line for more than an hour. So we arrived at 8 AM (they open at 9 AM), and only one other group got there when we did. It was just us. 

Where you stand is in the direct sun, so we all went around the other side of the building to sit in the shade but quickly realized you can't do that because other people lining up won't see you and get in line (cutting in front of you and not caring you were there first) so we got back in the direct sunlight. It was pretty warm in Chicago this time of year, so standing in direct sun for an hour is not fun. My husband returned to our Airbnb because we were just a few minutes away to get an umbrella to help. 

The line quickly grew, and by 8:40ish, it was deep. I didn't count, but it could have easily been 80 - 90 people. Even though getting there an hour early was annoying, it was imperative. The cafe is small, so you're not just waiting in line, your waiting for the first wave to get in and out.

We were the third group (you go in one group at a time, so you still have to wait once they open) and ordered at the counter and were directed what table to sit in; you cannot choose where you sit. This is for efficiency of course. 

We both ordered breakfast sandwiches, a pastry each, and coffees. I got the breakfast sandwich with egg, hashbrown, and longanisa. For coffee I ordered the "oh, hot yam" (ube latte with coconut sap) and the Ube and Huckleberry Basque Cake. You can tell they have their flow down to a science because the food came lightning fast. Even the group of four next to us who ordered the breakfast plates got them very fast. We waited an hour to maybe be in the cafe for 10 minutes. Of course, you want to avoid lingering when 100 people are outside baking in line. 

I enjoyed my sandwich, but I really LOVED my coffee. The pastries were tasty as well. But was it worth waiting in line for an hour? No.

Yes, I was aware you can order pick up and forgo the lines, but I wanted the whole experience. Knowing what I know now, if you want to go and want to get in line, order takeout, but still be aware of when you order it because things can still sell out.

GIRL AND THE GOAT

Neighborhood: West Loop

Girl and the Goat was already on my list when I started planning, but when I asked for recs, it was one of the most recommended places to dine. The restaurant describes itself as having bold, global flavors, and after my dinner, I can attest that is true. We made a reservation ahead of time to ensure we had no issue getting in, although if you go early when they open during the week, you can probably walk in.

The restaurant offers small plates, so we ordered a few and shared. Each dish just exploded with flavor. We ordered olive focaccia, goat empanadas, sautéed green beans, crispy short ribs, and plantain tres leches for dessert. This was one of the better meals I’ve had in any city, and I would recommend it when visiting Chicago.

DAISIES

Neighborhood: Logan Square

I took a gamble on Daisies for one of our dinners since I hadn’t heard much buzz about it. I was going off its accolades, including a Bib Gourmand and the Green Star for gastronomy and sustainability. They also make sure that their staff receives equitable pay. It checked a lot of boxes on paper. Also, a little secret I have when researching a new restaurant in another city: I see if the Strand is following them, and that tells me something good.

The food is pasta-focused, with a midwestern flair.  

My cocktail for the evening was the Late Summer Preserves (Clarified) peaches, brandy, maple, lemon, amaro, milk, fizz. It was not something I would usually order, but it was awesome. For food, we ordered the fritto misto (which I could have eaten all evening), the Pappardelle, and the Sunchoke Gnocchi (my favorite). Not only was the good, but the service was outstanding. It's not an overly upscale atmosphere, yet the elevated service makes it feel like a memorable experience. 

BUNGALOW BY MIDDLE BROW

Neighborhood: Palmer Square (near Logan Square)

Bungalow by Middle Brow was not on my initial list, but it was recommended to us by my dear Grace of Nomad Bakehouse, whose taste I trust implicitly. They make everything in-house, from their dough to wine and beer. Our meal was simple: a huge kale salad and one of their soppressata + hot honey pizzas. It has a really nice crust and flavors. If you happen to be in the area, it’s a fantastic local place to grab some food and seemed very family-friendly. 

PEQUOD'S PIZZA

Neighborhood: Lincoln Park

On my last visit to Chicago, we went to Gino’s East for a deep dish. That was my first Chicago deep dish, and I really didn’t like it. It felt like a heavy pie, and I remember the sauce being overly sweet. I hadn’t planned on trying deep dish again, but we decided to try it at Pequod’s, mainly because people who felt like I did about deep dish said they had enjoyed Pequods. 

We made a reservation and were sadly taken into the dark upstairs area with almost no natural light, so I don’t have great pictures, but the pizza was delicious. I like the caramelized cheese that forms on the crust, and while it’s deep, it’s not ultra thick and hard to get through. We waited about 50 minutes for the pizza, and they were not that busy, so if you have somewhere to be at a particular time after you eat, keep that in mind.

Au Cheval

Neighborhood: West Loop

Au Cheval is home to what some say is among the best burgers in the U.S., and it’s known that people will wait hours to eat it. I don’t normally buy into that kind of hype, but enough people told me it was worth waiting in line for that. I decided to try it, but only if the wait time was short. On Tuesday, after our architectural boat tour, we decided to see what awaited us. Our Uber driver who picked us up saw our destination and claimed he ate there regularly. We told him our plan, ready to bail if there was a wait, and he assured us at that time of day on a Tuesday, we’d be fine, and he was right. We walked in and were sat immediately.

Let it be known - Tuesday at 2 pm, you might walk right in just like we did.

Here is what you need to know. You only need a single cheeseburger ($16.99) because a single is two patties. What made the burger was adding bacon to it ($6.99). These aren’t some flimsy, thin strips like you’d get on an IHOP platter; this bacon is thick and seasoned. The burger was truly delicious, but I would not wait two hours for it, mainly because I’m not even really a burger person. So go in an off-time.

If you don’t want to bother, you can visit Small Cheval, their smaller sister concept. You probably won’t encounter a wait, and you can order online.

Mott St.

Neighborhood: Wicker Park

No offense to Mott St., but to be honest, it was our most lackluster meal in Chicago. That doesn’t mean it was a terrible meal, but with all the fantastic options in Chicago, I do feel like we would have been better off with another choice.

The burger that garnered a lot of buzz was just okay. The Thai-style papaya salad lacked flavor (which was pretty shocking), the fire chicken was drowning in too much sauce, and the imperial rolls were tasty, but I can get those unique ones here in Orlando.  

I would respectfully pass this on if it is recommended in your research. 

QXY Dumpling

Neighborhood: Chinatown

A quick afternoon in Chinatown meant lunch at QXY Dumplings. We were able to get a table right away, but it was a full restaurant at lunchtime. We ordered two types of dumplings, pan-fried and steamed. I liked them both pretty equally, maybe leaning a little more toward the flavor of the steamed dumplings. The two of us had no problem eating these without any leftovers. We did have an appetizer of cucumber salad, but I’d pass; it wasn’t as good as I’ve had other places. The cucumber was a little soft, and the flavor lacked. Stick with the dumplings.

Lilac Tiger

Neighborhood: Wicker Park

Lilac Tiger was a last-minute add-on when we realized it was a quick walk from our Airbnb, and we just wanted to snack, not eat a huge meal. This spot is South Asian street food with small plates. We ordered the cucumber salad, which was the spiciest I’ve ever encountered. Every fork full was followed by coughing and water gulping. We also tried the Sichuan calamari and the orange cardamom cake. It was a fun place to snack, and I enjoyed probably one of the best mocktails of my life. The “lime and the coconut” (Seedlip Grove 42, cinnamon, pineapple, ube, and coconut milk). There are no reservations here; first come, first serve.  

MANO modern Cafe

Neighborhood: Noble Square

Our last morning in Chicago was gorgeous, so we hit up one last cafe before heading to the airport. In my research, I found Mano Modern Cafe, another Filipino spot that wasn’t quite as popular as Kasama, but some said it was a more laid-back, easy-to-get-to option. The menu had similar items: breakfast sandwiches with longansia, to which you could add a hash brown, and rice bowls.

The only con was that I assumed it would be busy, so we ordered our food to pick up. It was done well before we arrived, so my sandwich was quite soggy. You could taste that all the elements were good, but I should have ordered it when I arrived. Thankfully, the hashbrowns were still crispy since they were packed separately. Don’t make my mistake. The Ube Matcha made up for the soggy sandwich. So try this spot if you want a Filipino breakfast but don’t want to brave Kasama.

Taqueria Chingon

Neighborhood: Bucktown

This was a last-minute lunch after a quick Google search of our area, and boy, was it a gem! I was a little worried when we walked in and saw $6 tacos on the menu. While obviously, that is still very much a wild price per taco, they at least came through in flavor, quality of the tortilla, and the amount of meat per taco. The flavors of the campechano reminded me of Hunger Street here in Orlando. I was really happy with this spot as my only taco fix on this trip.

Hai Sous

Neighborhood: Pilsen

Hai Sous is a Vietnamese restaurant with several Michelin Bib awards from the past few years. You can be fancy and go for the full-tasting menu or order a la carte. We ordered a la carte. We got the Grilled Prime Ribeye Lemongrass, mở hành, chili-lime-salt, Cải làn Chinese broccoli (tương tỏi, fried garlic), and Bún Chả Hanoi (Hanoi-style, clay pot grilled pork patty, rice noodle, crispy spring roll, charred pork broth, bib lettuce & fresh Vietnamese herbs).  

Our dining experience at Hai Sous was the perfect last dinner during our stay. Each dish was a burst of flavors, with the Chả Hanoi standing out for its incredibly rich and flavorful broth. What's more, the price point of $38 for a meal meant to be shared by two was a pleasant surprise. The meal concluded on a high note with a generously sized Vietnamese coffee cream puff. 

Kurimu

Walking down W. Division Street I almost screamed seeing a huge Miffy in the window of a shop across the street. I had no idea what it was, but I love Miffy (think Hello Kitty but a Dutch bunny) so I ran to her. It’s a local Chicago ice cream shop that just happened to be in the midst of a Miffy collaboration. Miffy’s face outfitted the shop, and there were themed treats. I bypassed those and went for something else - a Brown Sugar Boba soft serve. Simple and delicious. I now want Orlando to have a Kurimu of our own.

THINGS WE DID, SHOPS WE VISITED

Architectural Boat Tour

I would highly recommend an architectural boat tour. We booked ours through Chicago Line Cruises, and the cost was $50 per person. While that is not a cheap activity, I will say I felt it was worth it. The tour is 90 minutes long, and our guide was so well educated not just on the buildings but the overall history of Chicago. You get so much information during the tour, not to mention city views, that you'd never get on foot.

What to know is that if it's a beautiful sunny day, you will be in direct sun for the full 90 minutes (unless you go to the boat's lower level, which no one really does because it's not the same view). Bring a hat or an umbrella. You can get a sunburn in 90 minutes. Free non-alcoholic drinks are available, and if you want to purchase beer or wine, it's also available. 

WALKING 18TH STREET IN PILSEN

Pilsen is a cool neighborhood in Chicago that despite signs of hip restaurants and shops still is a main hub for the Mexican American community in Chicago. Hopefully that doesn’t change. 18th Street in particular was named one of “America’s Coolest Streets”. You can build a whole afternoon around exploring 18th Street ending with dinner there which is exactly what we did.

• EL Anticuario

• Pilsen Vintage

• Knee Deep Vintage

• 606 Records

• Trash

• Pilsen Community Books

• El Corazon Cafe

LIST OF OTHER SHOPS WITH NEIGHBORHOODS

• Reckless Records - Wicker Park

• Kokorokoko Vintage - Wicker Park

• Dusty Groove - Wicker Park

• Shuga Records - Wicker Park

• Signal Records - Wicker Park

• Neighborly - Wicker Park

• Paperish Mess - Ukrainian Village

• Lost Girl Vintage - Ukrainian Village

• Toy De Jour - Logan Square

• Nakama Toys - Logan Square

I hope you found this guide helpful!