Hi there! I know it’s been awhile – between work and other travel adventures, it’s been hard to find time to sit down and work on this blog. And honestly, I’ve had some trouble with getting the momentum to write. But I’m trying some new things out to hopefully get me more in the routine of posting here – which is good because I have a backlog of content to share. So stay tuned for more activity here! For now, here is what I got up to during a quick trip to Chicago in November 2025:
Sometimes, you do wild things to preserve elite mileage status (thanks for sucking me into the game, Alaska Airlines) – like fly to Chicago for a quick 24-ish hours of adventure.
Friday, October 31
9:30 pm-ish
How do you make the most of an eastward weekend trip when you lose time just by flying there? You (try to) commit to the red-eye. While others are out enjoying Halloween festivities, I risk looking like a ghoul from lack of sleep by hopping on a late night flight to Chicago.
Saturday, November 1
12:20 am
Flight takes off. I am thankful I have learned to sleep on planes. I somehow always managed to zonk out while taxiing before takeoff and wake up to find myself in the air.
6:01 am
Flight arrives at O’Hare. I. Am. Groggy. But I have a plan to make the most out of my few hours in the city.
6:20 am-ish
After the plane pulls into the gates, I swap out my glasses for contacts and change out of my comfy clothes in the airport bathroom before grabbing a rideshare to my first destination: Metric Coffee. Not only are they an acclaimed local roaster, but they also are open at 7 am, which is crucial to make the most out of my time in Chicago.
7:02 am
I arrive at Metric Coffee and get a drip coffee and a ham and cheese croissant to go with it. The seasonal bean blend looks interesting, so I grab that too, as well as a bag of dark roast as a gift for my parents. While it’s cold outside, the gazebo is the only spot to sit. I bundle up and sip my hot beverage as I watch a large local bike club assemble for the day’s ride by the coffee shop.
7:30 am
After re-scanning the map and my rough itinerary, I decide to walk to my next destination: actual (or second) breakfast at Kasama, a Michelin-starred Filipino joint whose breakfast sandwich got popularized by the television show The Bear. While I don’t watch the show, I am intrigued by the spot. Plus, I already had dinner reservations and I wanted the flexibility to wing lunch, so breakfast seemed like the right spot to slot in this hot spot. There are no reservations for breakfast, so the Internet informed me I should arrive early. While Kasama opens at 9 am, I am no stranger to standing in a queue, and with little else open at the time in the area that isn’t a whole other meal, I decide to walk the few dozen blocks to make space in my stomach for that breakfast sandwich. Along the way, I enjoy the fall colors and brick buildings, and spot a gelato store I mentally make note of for later.
8:15 am-ish
Thinking I’d be early, I am surprised to already find four or five parties in line for Kasama. While I wait in the cold, I decide to book a ticket for the Chicago Architecture Boat Tour from the Chicago Architecture Center. Despite the many times I had passed through and stayed in Chicago, I hadn’t done this particular tour, but a friend suggested it’s a good way to get off my feet and see the city from a different angle.
9:00 am
Kasama opens and the line is quick. As soon as I get inside, I see the large pastry and patisserie display – and start to second guess my breakfast order. I end up ordering a corn and blueberry danish to go alongside my longanisa, egg, and cheese breakfast sandwich. Drip coffee is a critical addition to this breakfast mix.
9:15 am
My pastry comes out first. It’s beautiful to look at, but hard to go halfsies on to split for later. A sweet corn cream bursts out of the white chocolate shells that have been molded to look like little corn. The blueberry compote is sweet, if not a little too sweet to the point where it masks the subtle corn flavor sitting on top. Sadly, I find the actual pastry a bit dry, so I mainly concentrate on eating the filling and leave the rest.
9:20 am
My foil-wrapped breakfast sandwich comes out. It’s hefty, with a sizable chunk of longanisa sausage, a large fluffy square of steamed egg, and a bright slice of cheese. The first few bites are good, but about halfway through the sandwich, I feel weighed down by its richness and sweeter flavor profile than how I would prefer my breakfast sandwiches. Some spice or vinegar would have helped balance everything out.
I eat a few more bites before clearing space to make room for another party to come in. By the time I leave, the line is already down the block and around the corner. Would I wait for that sandwich again? Probably not, but I’m glad I tried it.
9:43 am
I decide to walk to the nearest metro station to pick up a day pass for transit. It ends up being further than I anticipated because I forgot that Midwest blocks can be long.
10:20 am
My social media algorithm picked up my interest in Chicago and baked goods a few weeks prior to my trip, so it showed me a newer bakery called Daeji Dough Company that featured Korean/Korean-American flavors. Thinking I’d still be on the early side of service, I take the bus and walk a few blocks to the shop. But sadly for me – though very good for the business – they are sold out of nearly everything! Bummer, their tteokbokki croissant sounded delicious and savory. I guess I will have to check them out next time…
10:50 am-ish
A little more walking and my feet are starting to feel it, especially since I have been carrying a full overnight back with me since hopping off the plane. I also happen to be blessed with an increasingly sunny day. This is great – but my multiple layers to combat the cooler temperatures in the morning start to become a nuisance. I park myself on a bench by Lake Michigan and people watch for a few minutes as I pack away my sweater layers in my bag.
12:00 pm
After walking along the water for about 1.5 miles, I come across the Green City Market in the Lincoln Park area. I browse the vendors in hopes to find something for lunch, but end up sampling some raw honey kombucha from Jun Bug. I settle on a cup of the strawberry basil-flavored kombucha, which is dry and not too sweet despite being full of berry juiciness. As I am close to finishing my cup, a party of yellow jackets decide they want to sample my drink too. I quickly concede my cup to them with a bit of a yelp.
1:45ish pm
I end up being incredibly indecisive on my lunch options and head over to the Architecture River tour pickup spot area earlier than planned to grab a salad. I inhale it faster than anticipated, so I walk down to the pier to wait for my tour time. The attendants, however, offer to move up my reservation to an earlier tour so I don’t have to wait too long in the cold. At this point, I am feeling the effects of sleep deprivation set in so I prefer to keep the day’s agenda moving forward, so I take a seat on the next departing tour.
My docent has been a long-time volunteer and I am impressed with how many facts and anecdotes he can rattle off as we cruise along the Chicago River. Over the 90 minute tour, he shares how the cityscape by the water was shaped by history, commerce, the environment, and trends of the time. As a fast walker who doesn’t often pause to look at buildings, this became a nice opportunity to do so and marvel at the various styles of layering architecture in the city center. I especially enjoyed seeing a water-level parking spot for some subway cars, and a map of Chicago etched on the side of a building that you’d only see if you were on the waterside.
4:42 pm-ish
After browsing through some stores in the Loop – including tracking down some truffles from Chocolat Uzma at the Starbucks Reserve Roastery, since I couldn’t visit their brick-and-mortar location on this trip – I take the train to the Wicker Park neighborhood for my dinner reservation, though I am early to my spot again. I decide to park up at a nearby bar called Truce and slowly sip on a cocktail.
5:55 pm
I arrive early for my dinner reservation at Mirra, a Mexican-Indian fusion restaurant that caught my eye while browsing through the list of partnering OpenTable restaurants on the Chase Sapphire Reserve portal (this has become a “maintain the perks” and “use the perks” trip). The perils of solo dining sink in as I scan the menu and wish I could have more dishes than what my stomach can accommodate.
I end up asking my server for some advice and his favorites, and to help me select a glass of Mexican Viogner wine that would pair nicely with the meal.
6:13 pm-ish
The wine first arrives, and while my taste buds are still recovering from my previous cocktail that was very strong and alcohol-forward, I enjoy the dryness and crispness of this white wine.
First to arrive: crispy “tacos” with Hudson Bay scallops, Mexican green curry, nopales pico, and ikura in crisp fenugreek roti; and a charred cauliflower salad with yogurt-agave dressing, morita-peanut salsa macha, hominy-madras crunch, and herbs.
The tacos are sensational and are a perfect few bites. The creaminess of the fresh scallops and pops of ikura mellow out the pungent and punchy green curry sauce, while the nopales pico and the taco shell-shaped roti give a balanced crunch to the dish. I could easily eat another plate of them. The cauliflower, meanwhile, is perfectly charred and delicious. It is the right amount of tender to stick my fork into, but soft enough to provide an in-between textural contrast between the smooth dressing and the crunchy toppings.
6:45 pm
My main dish – which my server highly recommended – arrives: Skull Island prawn chaat, grilled and served with chaat yogurt, cilantro-mint chutney, and salsa negra. If younger me were in the room, she would have stopped eating at this point, because she did not like shrimp or prawns. But since I have started to enjoy more course meals where I cannot always control what I will eat – and would, anyway, prefer not to get in the way of the chef’s creations unless I had an allergy – I have started to enjoy foods that I did not like as a kid. This is growth!
These prawns are big and meaty and are served with the shell mostly on, which means the best way to enjoy them is to get in there with my hands instead of a fork and knife. I tear the prawn head off of the body meat and sink my teeth into the juicy flesh, which is smoky and warm from the grill. I get an immediate cool-down from the yogurt, but the next layer of flavors hits as the spice from the chutney and salsa negra settle in. The more I eat, the hotter things get, and I soon find myself in a particular rhythm while enjoying the dish: get some meat, grab some topping, slather on the yogurt, and eat – and repeat. The herbs bring in a balanced freshness to the dish; I especially like the fried curry leaves that add another bit of crunch.
I clear the plate pretty quickly. All that is left are the shells of everything; I even took some time to suck out the prawn heads (there is no clean way of writing that sentence). As I sit and digest while debating dessert, the table next to me voices their regret for not ordering the prawns after seeing me demolish them. I suggest they add it onto their order while they can.
7:30 pm
I finish dinner, satiated but craving something sweet but lighter than what Mirra had to offer on their dessert menu. I recall the Black Dog gelato store I walked by earlier in the morning so I take a car to the East Village neighborhood. Their dairy-free cranberry yuzu gelato hits the spot. After all the warm spice from dinner, the cooling tartness is a welcome palate cleanser.
8:10 pm
After savoring my gelato, I decide to call it a night. Sure, I can continue my exploration into the night but I am ready to stop schlepping my overnight bag with me everywhere. I call a car to take me to my hotel by the airport, which will help with the early morning departure tomorrow. After checking in, throwing my bag down, and lying down, I am even more confident I made the right choice to have a quieter evening. My phone says I walked about 25,000 steps.
Sunday, November 2
4:00 am
I am awake. I am due to leave on the first Alaska flight back to Seattle, which gets me in at around 9 am. Although I’m grateful that this plan helps me gain time back for the rest of my weekend, as soon as I get out of bed, I feel the urge to get on the plane as soon as I can so I can fall back asleep. I quickly finish packing and grab the reserved airport shuttle to head to O’Hare.
4:55 am
I am through security and am at my gate, waiting for boarding. I try not to doze off.
6:00 am
My flight leaves the gate, I think around this time. I am not sure because as soon as I sit down, I am fast asleep. Grateful that I got upgraded to first class for a very comfortable flight home – which is one of the reasons why I enjoy having status, the game that I buy into and the reason for this trip. While it was a (very) quick one, I’m glad I got to enjoy a nice autumnal day in the city, and fill my hours with lots of sights, bites, and steps! (Almost had a triple rhyme there) Until next time, Chicago.
Check out where I visited!
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