20250830_084003Architecture along the Chicago River (August 2025)

The crown jewel of the Midwest, Chicago is the third-largest city in the United States. Home to over nine million people in its metropolitan area, this Illinois city is a huge industrial, financial, and transportation hub, not to forget a massive tourist attraction that draws in 55 million visitors each year. There’s no doubt that the so-called “Windy City” or “Chi-Town” has a large cultural and economic impact not only in the nation, but also the world.

Originally the land of the Potawatomi people, this region had initial contact with non-natives in the 17th century with the arrival of French explorers and fur traders who passed through to conduct trade and commerce. It wasn’t until 1790 that Jean Baptiste Point du Sable, a black freeman, became the first non-indigenous person to permanently settle in the area– today, he is considered the founder of Chicago, which is really quite extraordinary for a POC!

Following the War of 1812, Chicago grew rapidly as its location was strategic for transport connections (i.e. railroads) from the East Coast heading west, as well as access to water along the Great Lakes in the north and the nearby Mississippi River flowing south. Despite the Great Chicago Fire in 1871 that destroyed a lot of the Financial District, the city continued to flourish and gave rise to other industries like manufacturing, education, sports, and entertainment.

All of this is thanks to immigrants from all over the world who came to Chicago for better opportunities and a better life. Throughout the 1890s to 1910s, the “Windy City” saw an influx of European immigrants, especially Poles and Italians before Mexicans, Puerto Ricans, and African Americans arrived following the World Wars. The city is still extremely diverse to this day, with much of its food and culture reflected in the various communities spread throughout town.

I visited Chicago over Labor Day weekend last year; I’d been meaning to see “Chi-Town” for the longest time, and I finally had the moment to check it out. In addition, it was also my first time in the Midwest, and I was curious to see how the culture in middle America was compared to the West Coast, where I was born and raised for most of my life. Although I’m aware that Chicago, a big city, isn’t reflective of the entire Midwest region, I still got a taste of it in urban form (as well as hopping over to Wisconsin for a more Midwestern experience– more on that later)!

Right after I clocked out of work on Friday, I headed straight to the airport to catch my 22h50 flight over to Chicago. It was an overnight flight, and unfortunately, I did not sleep at all during the four-and-a-half-hour journey over. I was utterly exhausted once the plane landed in O’Hare International Airport at 4h30 local time, but regardless I pushed myself throughout the day to explore as much of the city as possible.

Since I’d arrived so early, the metro (or “the Metra,” as the locals call it) wasn’t open yet, so I waited a bit before getting the first ride out at 5h00. I took the Metra, then the bus, over to my first destination of the day: the Starbucks Reserve Roastery. There are only a few of these roasteries in the world, and Chicago’s is the largest and newest of them all, having opened in 2019 at 3300 squared meters over five floors. This isn’t your usual Starbucks, as the Reserve offers food, drinks, and merch that you can’t otherwise find at a typical Starbucks, and it’s a popular tourist attraction requiring you to arrive early to beat the crowds.

20250830_062730Starbucks Reserve Roastery

There were already a few people lined up outside the Reserve once I arrived, and I waited in the queue for the doors to open at 6h30. Soon enough, we were let in– at first, I’d wanted to check out the second and third floors for the dine-in cafΓ© experience, but apparently, they didn’t open until 8h00. However, the first floor was already open, which offered take-away drinks and pastries. I puttered around on the first floor for the first 90 minutes, grabbing a coffee and pastry as an early breakfast while waiting for the other floors to open.

20250830_080949All the delicious baked goods

Chicago’s Starbucks Reserve is, indeed, massive. It has an industrial look to it, with tall copper tubes that transport coffee beans through all five floors and rotating machinery preparing pastries. There’s a sort of Willy Wonka vibe to the Reserve, and I can see why it’s so popular among tourists– it really is that eye-catching!

20250830_064657First floor of the Reserve


20250830_071840All of the bean containers

Unfortunately, even though I waited and managed to see the second and third floors once they opened at 8h00, I didn’t have much time to really take them in, as I had to leave to make it in time for the Architecture Boat Tour. I’d purchased my ticket online in advance, but I had to head to the docks to redeem it. While I didn’t have much time to explore all of the Starbucks Reserve on my first day, I ended up returning on my last day to take my time and enjoy it (more on that soon).

I headed on-foot along the Magnificent Mile to the meeting point, taking in the high rises and trendy stores along the way. Soon enough, I reached the docks to redeem my ticket, and I got in line with several dozen other passengers for the first ride out at 9h30. The boat tour lasted 90 minutes, and the guide was excellent in providing so much information about the history and different architectural styles in the buildings along the Chicago River. It was also a beautiful, somewhat blue-sky morning, which made for lovely views and photos. I shamefully admit, I fell asleep for part of the tour, as I was so sleep-deprived, but I still learned a lot and felt my money was well-spent!

20250830_084723Just before departure…


20250830_104719Chicago skyline

The Architecture Boat Tour ended around 11h00, and I continued my stroll down Magnificent Mile. I ended up deciding to have lunch at a tearoom that also served Russian cuisine during lunch hours. There are many Russians who’ve settled in Chicago, especially in the early 1920s following the aftermath of the 1917 Russian Revolution. That said (and given the fact I love Eastern European food), I tucked into a large spread of varenyky (dumplings), goΕ‚Δ…bki (stuffed cabbage), and medovik (honey cake), all which were fabulous– I was more than satisfied.

20250830_114121Spinach varenyky


20250830_115557GoΕ‚Δ…bki with bulgur wheat and carrots


20250830_121148Medovik

At the risk of this post getting too long, I’ll recap the rest of my first day in Chicago in the next post. Until then! πŸ™‚

— Rebecca

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Published by Rebecca

Blogger, world traveler, poet, foodie, part-time penguin. Welcome!

63 thoughts on “Destination: Chicago, Illinois (Visiting Starbucks Reserve, Taking the Architecture Boat Tour, and Getting Russian Food– PART 1)”

  1. Oh another memorable spot but not for me too windy too cold and too much snow! I visited a couple times my best friend from there visited me in France ,and have a cousin living there. That is plenty for me Cheers

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  2. I very much love the first photo of architecture and all the modern skyscrapers along the Chicago RiverΒ  – it looks so beautiful. I hope you liked buckwheat. It is a major staple of traditional and everyday Latvian cuisine and so popular that nowadays you can even find it in shops around Sligo town, Ireland. Thanks for sharing, and have a good day πŸ™‚ Aiva xx

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    1. Buckwheat is okay; I’ll eat it, but it’s not my favorite grain to have πŸ˜… All the same, it went well with the Russian food I had, and it made for a hearty meal! Thanks for reading, Aiva, and more on Chicago coming soon!

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  4. Rebecca, thanks for visiting our city. I’ve lived in the suburbs my entire life, as my parents grew up on the southside. It’s an amazing city, yet also a huge mess. I’m excited to one day move out of here, but as you mentioned, it is quite a great place to visit.

    Thanks!

    Reid

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  5. I also visited Chicago and particularly loved the architecture along the river, so the Architecture Boat Tour brought back some great memories. The way the skyscrapers rise directly from the waterfront creates such a spectacular urban landscape. I can understand why the tour was a highlight, despite the sleep deprivation after that overnight flight!

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    1. I love to check out the architecture whenever I visit a new place, Chicago included. Despite being sleep-deprived, I still enjoyed the Architecture Boat Tour and learning about the various styles throughout the city (at least, from what I learned while awake, haha)!

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  9. What a packed and incredible start to your Chicago trip, Rebecca! πŸ™οΈ Pushing through an overnight flight is no small feat, but starting the morning at the Starbucks Reserve and taking in those riverfront views on the boat tour sounds so worth it. That Russian food spread looks absolutely deliciousβ€”can’t wait to read Part 2! ✨

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  12. Rebecca, what a delightful read! Your detailed exploration of Chicago; from the Starbucks Reserve’s Willy Wonka vibes to the architecture boat tour to that incredible Russian food, makes me want to book a trip immediately. The varenyky and medovik look absolutely divine! I loved learning about Chicago’s rich history and immigrant communities. Can’t wait for part 2! πŸ™οΈβœ¨

    Love
    Khadija ❀

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    1. You’re right! Starbucks Reserve looks like something out of Willy Wonka’s chocolate factory, except make it coffee beans! It was a touristy, yet whimsical visit, and I ended up returning to take my time and explore more of its floors, even sitting down to enjoy the food and drink. More on that to come soon!

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  13. That sounds like such a packed first day, especially after an overnight flight with no sleep! I’m impressed you still managed to fit so much in πŸ˜‚

    The architecture boat tour would probably be a highlight for me too. I love how exploring a city’s architecture can also give you a glimpse into its history and development. I also had no idea the Chicago Starbucks Reserve was five floors!

    And that Russian lunch looks like a very well-deserved reward after all that walking, especially the medovik. Looking forward to Part 2!

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    1. Thank you! Red-eye flights are tough, but the advantage is that you arrive as soon as the day starts, which gives you more time to explore! The Architecture Boat Tour was fun and informative and being an architecture geek, it was right up my alley. More of my time in Chicago is coming up, so stay tuned!

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  14. Landing at O’Hare at 4:30am with no sleep and still powering through the Starbucks Reserve queue AND a 90-minute boat tour is impressive stamina. Falling asleep partway through the architecture tour is completely fair, though – we have done the same on more than one guided anything after a redeye. The varenyky and medovik lunch sounds like the perfect reset.

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    1. With limited time, it’s best to maximize the visit with as many activities as possible! Not only do you cover a lot of the city, but it also keeps you awake and adjusted to the time-zone change. It wasn’t easy getring through that first full day in Chi-Town with zero sleep, but I still saw a lot and had lots of fun!

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  15. You did well to fit in so much activity that morning after your sleepless night. I never sleep on planes so I sympathise! You’ve taken me back to my own visit to Chicago. I passed that Starbucks but didn’t go in as I really don’t like either their coffee nor the company as a whole. But the boat trip I did do, and thoroughly enjoyed πŸ™‚ Looking forward to hearing what else you got up to on your visit.

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    1. Indeed! Thanks, Sarah. Getting zero sleep on the flight was a rough time, but I managed to get through my first day of visiting Chicago by willpower! I agree that Starbucks isn’t my preferred coffee, but I decided to check out its Reserve for its gimmicky nature. More on Chicago to come soon! 😊

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  16. Not being able to sleep on the plane is the worst feeling, but it sounds like you managed to make the most of of your first. I’ve never actually been to a Starbucks Reserve but it does look like it would be fun to visit. Also, I didn’t know any of the history of Chicago so I enjoyed learning that.

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    1. Thanks, Diana! Not being able to sleep on a flight is rough, but I powered through to make the first day in Chicago worth it! Starbucks Reserve is a cool experience, even if a bit gimmicky…more of my time in the Windy City to come soon!

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  20. Wow you did so well to go straight from work to the airport, land at 4am with no sleep and do a day of exploring! that is hard core!! I love the look of the Starbucks reserve and Chicago’s skyline is really striking.

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  21. I have a post of Travel-Inspired Baking: Georgian Medovik in my drafts folder! I’ve been to Chicago a few times, and once I took the architecture boat tour. I’m not much into architecture, but I really enjoyed it. I’ll be curious to hear your impressions of Wisconsin (my home state).

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  24. Ah Chicago, I love that city and had a fabulous five days there back in 2012, way before that Starbucks joint even opened. Like you I also enjoyed the architectural boat tour, with scenes of Ferris Bueller playing out in my head. Well done for pushing on through, exploring is tough on no sleep, no matter how excited you are. I’d say that nap on the boat was well-earned.

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    1. Haha, I think I missed a third of the commentary on the architecture boat tour due to nodding off! All the same, it was a fun morning on my first day of Chicago, and I’ll recap the afternoon in the next post! Thanks for reading, Leighton 😊

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  25. I can’t blame you for falling asleep during sime parts of the boat tour. After taking the night flight without getting any sleep, plus the gentle rocking of the boat, I’m sure it was the perfect recipe for a nap. Looking forward to more posts about Chicago.

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  26. Thanks for sharing the history of Chicago at the start, it added a nice dimension to understanding the city! All I knew of the city before is that it’s cold! πŸ₯Ά My husband went once years ago, and he still compares all cold weather he experiences to it. πŸ˜…

    I’d love to visit one day (preferably in summer!), and the boat tour and Starbucks look like awesome stops.

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    1. Thankfully, I went towards the end of the summer, so Chicago was nice and warm! I can’t imagine just how cold it gets in the winter (nor do I want to live it)! The warmer months are the way to go, and I hope you can head over to the Windy City some day πŸ™‚

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  27. We visited Chicago back in 2023 at the start of our Route 66 adventure and I wrote about it in my blog:https://amidlifeadventure.org/2023/06/16/impressions-of-chicago/. It’s city we definitely want to return to mainly in order to visit the new Obama Centre, its very high on our must dos!
    We also did the Architecture Tour.
    Crazy fact: My local council clerk and I popped into an independent bakery/cafe recently and had Medovik cake. She loved it so much I secretly got my husband to find a receipt and make it for her 😊

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    1. Nice!! Looks like the Obama Centre just opened this June, and it looks really cool! Medovik is delicious, and I’ve tried recreating it myself (although not very successfully)! I’d rather just buy a slice to enjoy πŸ˜†

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  28. Starbucks Reserve looks like more of a museum than a cafΓ©. I can see why so many visitors to the city are drawn to it! We also did the Architecture Boat Tour when we visited Chicago back in 2016, and thoroughly enjoyed it.

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    1. Indeed! Starbucks Reserve is definitely more of a tourist attraction than cafΓ© (to be honest, the food and drink were just-okay, the quality about the same as what you can get at any regular Starbucks). The Architecture Boat Tour is iconic, and it’s definitely a must-do while in Chi-Town!

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