A couple of months ago, one of my high school best friends messaged me and asked if I wanted to go to Chicago for Labour Day long weekend. Well, if you know anything about me, if it involves “traveling” and “long weekend,” I’m in 95% of the time. As medical students, we’re often asked to sacrifice our time, our relationships, and sometimes our sanity on our road to becoming real, productive members of society.
We’re about 2 weeks into our second year, and I’ve found this to be true: if you don’t take advantage of weekends, medical school will take advantage of you; thus, I booked a pretty expensive flight to Chicago, ready to go on another whirlwind adventure.
So how long was I in Chicago exactly? 2.5 days – short, but 100% worth it.
Here are some fun facts my friend researched:
- Did you know that Picasso, Joan Miro and Marc Chagall all have contributed artwork to the streets of Chicago
- Jazz was invented here
- House music started here
- Improv comedy was invented at the University of Chicago – the original theatre is still running
- The world’s first skyscraper was built in Chicago
Here’s a basic map of what we did to maximize our time in the windy city. If you only have a couple days here, the things I starred I HIGHLY recommend you check out:
Friday (0.5 day):
- Logan Square
- Division St. (we ended up at Pub Royale)*
- Sleep (because we were both completely exhausted)
Saturday (day 1.5):
- Millenium Park & The Bean*
- Art Institute of Chicago*
- Naf Naf Grill
- Glazed and Infused
- River North*
- Second City – #Dateme: An OkCupid Experiment*
Sunday (day 2.5):
- Downtown Hyde Park
- Bucktown/Wicker Park*
- Milwaukee, Division, North and Damen Streets
- Jeni’s Splendid Ice Creams
- Chicago Picasso (Daley Plaza)*
- Miro’s (across from Picasso’s city statue)
- Navy Pier (in Streeterville)
- Vosges Haut-Chocolat (you get a free truffle if you check in on Yelp!)
- Pizzeria Uno* (first deep dish pizza place in Chicago)
- Eataly (not really a “site,” but great place to explore and try wine while waiting for your table at Uno’s)
If you’re still reading, here’s a more fleshed out version of our weekend in Chicago:
I left Toronto at 5:30pm on Friday (after being responsible all morning eg. actually going to class and attending meetings), and got there at 6:45pm. Once I got there, I discovered something brilliant, that would change my entire experience in Chicago. UBERPOOL. My drive from ORD to our AirBnB in Hyde Park was about an hour and 20 minutes, and cost me $20 USD (crazy I know). Once I got there, me and my friend were starving, so we of course called another Uberpool, and decided to go check out the bars and restaurants in Lincoln Square.
After driving for about an hour though, we quickly realized that the restaurant we were trying to go to didn’t seem to exist, and asked our driver if she had any recommendations on where we could go to eat and drink (it was now 10:40pm). She suggested we check out Division St., which is a long street that’s known to be pretty fun on weekends. After another 30 min (total drive time = 2 hours), we discovered Pub Royale, and decided to grab drinks and food here. In total, our UberPool cost about $24 USD, which is incredible considering we drove for 2 hours.
I really loved Pub Royale, an Indian style pub. I highly recommend you check this place out if you’re in that area, they have great Indian food and drinks. My friend ordered the Chicken Tiki Kati Roll, which she repeatedly told me was amazing, and I ordered the eggplant curry, which was delicious and just what I needed at 11pm at night. After talking, drinking and eating for 2 hours, we decided to head home to get some rest before a big day tomorrow.
On Saturday morning, we leisurely woke up at 10am, and headed downtown to check out the Art Institute, after grabbing some coffee at Bowtruss Coffee Roasters. I loved the art institute – they had an incredible collection of Impressionist Art, and I loved their special exhibits. The student price is $19 (adult is $25), and I have to say, you could really spend a whole day here (Open: 10:30am – 5:30pm most days, 8pm Thursdays). If you only have a couple hours though, here are my favourite exhibits/collections:
- American after the fall: Painting in the 1930s
- Edward Hopper
- Grant Wood
- The New Contemporary
- Andy Warhol
- European Painting and Sculptures
- Thorne Miniature Rooms
- Chagall Windows
The Bean of course is pretty iconic – but I recommend going when it looks like it’s going to rain. There are always so many tourists there when it’s sunny, spare yourself and go on a cloudy day.
Sooo skipping to that evening, I highly recommend trying the doughnuts at Glazed & Infused, they’re really delicious, fresh, free from preservatives and all natural (whatever that means). They have a lot of creative flavours, although my favourite by far was the red velvet. They have a 2 for 1 (or 2 for 2 depending on who the cashier is), so make sure you stop by during happy hour!
After drowning our palates in sugar, we headed out to grab drinks before seeing the comedy show at Second City. I’ve always wanted to check out Three Dots and a Dash, a Hawaiian themed tiki bar, so we found our way to the alley and the unmarked door with glowing blue lights. It’s easy to miss this place before the crowd gets here, but basically look for the security guards standing outside of club-like venue in a shady alley. They have the most amazing decorations and drinks, and the bartenders are super talented. I highly recommend the Missionary’s Downfall ($14) and the Banana Daquiri ($13). The first is sweet and tart, while the second one just taste like sugar, fresh bananas and lots of rum. We spent a couple hours here, but it turns into a club around 10:30/11pm. When we left around 10pm, the lineup outside was down the block, so it’s probably a good idea to eat and drink here, then stay for the party after.
The show, #DateMe: An OkCupid Experiment, was next on our agenda.
LOVED it. We originally wanted to see the Second City improv but it was sold out, so we bought tickets for this instead ($39 after taxes). It was really hilarious, and the the improv bit was gold. It was witty, relatable and apt for our generation. We were super lucky since our Airbnb host was one of the production managers for the show, and reserved amazing seats for us with 25% off our orders. That being said, COME EARLY since there’s no reserved seating, and the theatre is pretty intimate. There were a ton of couples there – it would be perfect for date night.
Sunday was another perfect day. We started the day off at Obama’s favourite diner, Valois in Hyde Park (I recommend the veggie egg white omelette with a biscuit – $7). He’s from Hyde Park, so you see lots of shout outs throughout the neighbourhood. After, we took public transit to Bucktown/Wicker Park and wandered around for the next few hours. There are tons of stores, bars and restaurants here, and you could easily spend half an afternoon browsing, eating and drinking. Also, if you come around 4pm there are tons of happy hours to be enjoyed :). Skipping ahead to deep dish pizza, here’s my two cents:
- Lou Malnati’s: I tried this the last time I was in Chicago. It was good, but it’s a chain restaurant and there’re definitely better deep dish places in the city. If you’re looking for truly amazing or iconic deep dish, I would skip this place. It also has a super long wait time once you sit down, but that’s because deep dish apparently takes a long time to make fresh
- Giordano’s: another chain, you can actually get this at the entrance of Navy Pier. I’ve never tried it, but again, probably not the best or most iconic
- Pizzeria Uno: we decided to eat here because it’s the birthing place of deep dish pizza. It’s pretty famous, the pizza was delicious, and the wait wasn’t too too bad (we got there at 6:30pm and were seated by 7pm). I recommend it!
- Pizzeria Due: I think it’s owned by the same people as Pizzeria Uno. It’s right across the street and it’s the “second” deep dish pizza place. The wait is similar, about 30min-1 hour and I imagine the pizza is similar to Uno (the menu is the same)
- Pequod’s Pizza: A local told us to try this place for deep dish pizza. Supposedly it’s really good but we never tried it. If you do, let me know!
I ended up busing home from Chicago, which took about 12.5 hours total ($89). It wasn’t too bad, but we did have to change buses 3 times, so don’t expect uninterrupted sleep if you’re taking the Greyhound. It also gets super cold on the bus, so wear pants and bring a sweater.
Overall, I had an AMAZING time in Chicago, and am so looking forward to the next time I get to visit again. If you have any questions about my trip or want any input on your own trip, feel free to contact me with comments and questions :).
In the mean time, can’t wait to bury my head in my books for the next couple months, stay tuned for my next exciting adventure: USMLE STEP 1 (Note: sarcasm – I’m literally terrified of getting my ass whooped)
Side note: I can’t believe I ran into one of my old Berkeley/PhiDE friends here (TWICE)! She was here for a wedding but we literally kept running into each other. When they say it’s a small world, I guess they really mean it :p