2 Days in Chicago

This past week, I spent Thursday and Friday in Chicago with my sister to see the BLACKPINK concert!

This was actually my second trip to Chicago (the first time was Lollapalooza 2021) and it was such a fun couple of days (even if we both ended up getting sick).

We had the top goals for the trip of:

• Seeing some jazz / going to a speakeasy
• Watching improv
• Having a Chicago hot dog
• Getting some local beer
• Visiting:
  • Lincoln Park Zoo
  • Millennium Park
  • River Walk

Some recommendations I got from co-workers that we didn’t have time for were:

• Historic Hotels (The Drake / Palmer House / Congress Hotel)
• Deep dish pizza (Giodano’s, Lou Malnati’s, or Pequod’s)
• Sandwiches (Redhot Ranch, Al’s Beef – specifically the combo hot, Parson’s Chicken & Fish)
• Cuban food (90 Miles Cuban Cafe)
• Mexican food (Big Star)
• Neighborhoods (Bucktown, Wicker Park, Logan Square)
• Brunch (Lula Cafe & The Chicago Diner)
• Museums (Museum of Contemporary Art, Field Museum)
• Blues (Kingston Mines)

And we did some research with the following sites:

• TimeOut best things to do in Chicago
• John Hughes Movie Locations
• Thrillist best things to eat in Chicago

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Day 1: Downtown Chicago

We both flew into O’Hare around 9AM and took the metro into downtown Chicago to drop off bags at our hotel. For our two day trip (3 days including our flight out), we each picked up 3 day metro passes for $15/each, which was great for being able to hop on any of the rails or bus lines throughout our trip.

We started off our morning at Hanabusa Cafe, which is a Japanese soufflé pancake shop near Millennium Park. I had gone there last time I was in Chicago and completely fell in love with their Earl Grey Soufflé Pancakes, which are cloud soft and the perfect level of salty and sweet.

Thursday was actually quite hot (a high of 71F even in November), so we ended up stopping by Uniqlo so I could replace my sweatshirt with a lighter flannel and then checked out the Bean in Millennium Park and walked along the River Walk.

We were feeling a bit tired, so we grabbed a quick lunch at Eataly downtown. Eataly is an Italian food hall (started in Italy) with a few dozen locations globally. It was actually wildly cool with SO many options for food items you can’t find other places — like eucalyptus honey, sheep yogurt, and violet candy. We got a few treats there (mainly chocolate) and some very fancy sandwiches (which my sister said was her favorite meal of our trip).

After a post-lunch nap, we went over to Goose Island Brewhouse, where we grabbed a tasting flight and some amazingly good house-made chips and dip (seriously cannot more highly recommend them), before our Second City show! We saw the Best of Chicago show, which was super funny with some of their “classic” bits (a guy pretending to be a horse eating an apple messily had us ROLLING and the world’s most painful father/son baseball game made me feel like I was going to die of situational awkwardness). The show was $39/ticket for a 3-hour performance in a really small theater with great seats, so we got our money’s worth.

We wrapped up our night at The Drifter, an original 1920s speakeasy downtown below Chicago’s oldest bar The Green Door Tavern (built in 1872). You can find a good article on The Drifter here. The bar has a cool vibe with great drinks and amazing lighting / intimacy (it’s tiny). The door isn’t labeled, so you need to know that the entrance is what looks like a shelf by the bathroom.

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Day 2: Lincoln Park & Fulton Market

We kicked off a chilly Day 2 with breakfast at Goddess and The Baker, which is a cafe with several locations throughout Chicago. We both opted for smoked salmon items and holy-cow the Smoked Salmon Plate was amazing. The cafe has a very casual vibe — kind of like a Starbucks that serves sit-down meal items.

Our plan for the day was to walk up to Lincoln Park before our concert in the evening, so we started walking north and stopped first at La Colombe. There are La Colombe locations nationally but none near us, so we were quite excited. La Colombe is known for their cold draft lattes, which are…incredible. Imagine melted coffee ice cream, both in flavor and foaminess (but only 170 calories).

From there, we walked up through Old Town (stopping in some cute shops) to Lincoln Park. We hit up both the beach (my sister’s first time seeing a Great Lake) and the zoo, which was wonderful! I love that Chicago has a free zoo in the middle of Lincoln Park and there was enough inside exhibits that we weren’t completely freezing.

For lunch, we headed back downtown to grab Chicago hot dogs at Portillo’s! Multiple people had recommended Portillo’s as the best place to grab a hot dog and it did not disappoint.

Apparently, the components that make up a Chicago hot dog are:

• Yellow mustard
• Chopped white onions
• Bright green sweet pickle relish
• A dill pickle spear
• Tomato slices or wedges
• Pickled sport peppers
• A dash of celery salt

It is loaded and was really good!

After a short rest, we headed over to Fulton Market for a quick pre-concert dinner at Ramen Takeya, which was a great little izekaya. I had gone to Fulton Market last time I was in Chicago but it was dead early in the day. At night, it was bustling with the TimeOut Market food hall and lots of cute trendy restaurants. I’d highly recommend it as an area for dinner & drinks!

As our last activity of the trip, we headed to United Center for the real reason we were in Chicago — the BLACKPINK concert! They were so good and we sang our voices hoarse to all their bops — wrapping up a fun two day trip to the Windy City.