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Chicago Booth Weekend BA student Sydney Tsai

I was born in NYC and mostly lived in the NY/NJ area my whole life so I have gotten fairly used to the fast-paced lifestyle and personalities you often associate with the East Coast. I’ve worked in different roles and industries and eventually ended up in software sales for an engineering software company. In my free time, I pretend to be a foodie by trying out new restaurants and am always looking for something new to show my friends. My curiosity and adventurousness will make me want to try new places even if there’s only a 10% chance it will be great, rather than going somewhere I’ve been before that is just good. Coming from the city that never sleeps, I also like to stay out pretty late and have been known to close down a few bars.


7pm - Arrival in Chicago

It’s 7 pm and I just got into O’Hare. I’ll hop into an Uber and start heading to River North to drop off my stuff at the Aloft (off Mag Mile) I usually stay at. I’ll message a few friends to see who’s available for dinner but most have either eaten or are coming in too late for dinner. If I’m dining alone, I’ll hop into a fast casual place like Nando’s Peri Peri to get some delicious chicken, or Chipotle since I have a slight addiction to burrito bowls. Sometimes I’ll find other hungry compadres so we’ll end up going to a casual sitdown place like RAMEN-SAN Deluxe and get some nice soupy ramen. Usually, we can also grab a drink and catch up on what we did in the last week (or year and a half from COVID).

9pm- Night Out

After dinner, most people that are coming in on Friday nights start to arrive and want to get together. Either they’ll meet us at the restaurant we’re already at or we head over to a bar nearby. Since we have class the next day, we’ll go somewhere nearby like Timothy O’Toole’s for a casual drink to unwind from the week. Some of the latecomers might even be able to sneak in some food orders here before the kitchen closes. If we’re feeling lazy (and thrifty), we may even buy provisions from a 7-Eleven nearby and bring it to the lobby bar in the Aloft Chicago Mag Mile where we can chill at a bar while paying convenience store drink prices (yes, we asked if we can, and yes they do have a pool table and live music *exploding head emoji*). Sometimes we’ll get carried away talking until 3am but fortunately our room is right upstairs for us to crash and get ready for the next day.

Chicago Booth's Gleacher Center from above


7am - Before class

Depending on how late I went to bed the night before, I may decide to go on a morning run at 7am with some other Boothies in the Booth Running Club. Nothing wakes you up more than a morning run. After the run and getting ready for the day, I’ll head over to the fourth floor of Gleacher to get my mandatory two cups of coffee before class starts (don’t forget the coffee service stops at 11am). I’ll usually also bump into friends and catch up with people until the crowd starts thinning out and I realize I might be late for class. 

9am - Morning Class

I’ll head into my Applied Regressions class and try to get a seat on the side so I can still see the screen well but be able to sneak off to the bathroom after I process my morning coffee. Once the coffee kicks in, the quantitative concepts will start clicking and make sense. I had Professor Panos Toulis who was great at explaining these tricky stats concepts and could always answer questions in a fairly clear and concise way, even if the caffeine has yet to work its magic. After the class ends, I’ll feel like a statistics rockstar and will be ready to tackle the next homework assignment.

12pm - Lunch Time

As students begin hovering outside the classroom door, the professor takes the cue to end the class and I begin heading over to my next destination. There are usually many club activities that take place during the lunch hour so I’ll register for the most interesting looking event and go there (and hopefully snag a free lunch). In the rare event there are no events (or free lunches), I’ll head over to the lobby where you’ll find friends trying to figure out where to eat. We may grab something quick such as a bowl from Lyfe Kitchen or Naf Naf Grill (which are both delicious and healthy) but most times we’ll head over to Whole Foods to grab something to bring back to eat in the Gleacher cafe area. This is also the best time to catch up with those that you don’t see often as this may be the only time you are both in Chicago with nothing planned.

Chicago Booth students in a classroom

1:30pm - Afternoon Class

After lunch, I’ll head over to my Microeconomics class a few minutes early so I can reconnect with my group and chat about stuff besides Micro (since we talk about that enough during the week). As people are strolling in, you get to learn about the cool place they went for lunch, event they attended, or things they did that week. My professor starts the class and lectures about various Microeconomics topics. This class was really fun as we would go off into tangents and discuss how these theories apply to real life (also helps fight the after-lunch slump). You also get to see the diverse perspectives and experiences people have as we get into deep discussions about almost anything.

4:30pm - Saturday After School Happenings (SASH)

The end of class marks the true end of the week and everyone will gather in the hallways or lobby to say their farewells for the weekend or plan their next steps. What better way to end the week than to hang with some friends? Just about every week, we (the students) will decide on a nearby bar to go to for SASH. Once I find some walking buddies in the lobby, we’ll head over to the designated destination together to finally unwind after a long week of work and a long day of classes. We Boothies roll deep (and know how to party) so we’ll usually have about 50-100 people at SASH and end up taking over a section of the bar. If we’re having enough fun, you’ll hear about people missing or changing their flights just to keep the festivities going.

7pm - After SASH/Dinner

By this time, most people will have departed to catch (or try to catch) their flight or have other plans. Based on who’s left, we may decide to get an impromptu dinner at Parlor Pizza for some proper pizza (my NY side is showing) before heading over to Boss Bar to get some drinks and shake our tail feathers a bit.

Occasionally, I manage to convince some friends to visit for the weekend and then we’ll plan a night out. For dinner, I’ll try to head over to West Loop for a change in scenery since it’s easy to get stuck in River North with all the options they have and the proximity to Gleacher. You can never go wrong with sushi for dinner -- especially at Momotaro, which has some of the best sushi I’ve had (you must try the Kumamoto Beef To Hotate and the Aji Yakusugi).

10pm - After Dinner/Drinks

For a frosty beverage, if we’re feeling a little fancy, we’ll try to get into Lazy Bird around the corner to enjoy nice classic cocktails with live music. Or if we want something a little more casual, we’ll head over to Punch Bowl Social to grab some beers and play some games together. Whatever mood you’re feeling, it’s generally not too hard to find something fun to do at night.


11am - Coffee/Brunch

After a late night of fun and catching up with friends, it’s time to crawl out of bed and make the most out of the remaining time I have in Chicago. Coffee and food are a necessary start to the day so I’ll quickly pack and check out, head over to Wildberry Pancakes & Cafe by the Bean, and put my name down on the waitlist so we can get a spot in line. The wait can be long on the weekends, which means I’ll head over to Stan’s Donuts to get a cup of coffee in the meantime. Eventually we get seated and I’ll be sure to order some new interesting breakfast item I haven’t tried (and don’t forget to substitute for a side of specialty pancakes).

The 'bean' sculpture in Millenium Park

1:30pm - Afternoon Stroll/Work

After a hearty brunch and some dessert to top it off, I’ll head over to Millenium Park for a little stroll. It’s always beautiful walking by the Bean and seeing the energy from the tourists that are always hovering around it. After my food digests a little, it’s time to be productive. I’ll get my bag and laptop and head over to Gleacher to find a place to work on some assignments. Depending on how the weather is, I’ll either work in one of the side rooms with the windows at Gleacher or I’ll snag a table outdoors near the Northman right on the Riverwalk. Working outside with the sun along the river always makes it feel less like work and more like relaxing with a computer in front of me. And so I don’t feel like someone hogging a table, I’ll end up ordering a coffee or a beer depending on how productive I need to be.

6pm - Dinner/Farewell

With only a few hours left before my flight leaves, I’ll try to get some dinner so I don’t end up paying ~$15 for a crappy sandwich at the airport. I don’t have time to go to a sit-down place so I’ll head over to Portillo’s to get something quick. I’ll order the Chicago dog and resist my New Yorker urge to add ketchup along with the Italian Beef (dipped of course). After scarfing down my last meal to remind me of what I’ll miss in this city, I’ll head back over to the hotel to grab my stuff before grabbing a Lyft to get to the airport. As I near the terminal, I get nervous as I receive a notification saying my flight is boarding. Even though I almost missed my flight, I’m glad I was able to enjoy Chicago for as long as possible. Thankfully, I just have to wait until next weekend before repeating the fun all over again.

Sydney Tsai

Blog author

Chicago Booth Weekend MBA student Sydney Tsai