Weekend in Chicago with Family
Goals of Trip:
Celebrate my cousin's college graduation
Feed and entertain family members across generations, including family members ranging in age from early twenties to late eighties and with limited mobility
Keywords: Intergenerational, Wheelchair Accessible, Crowd Pleasers
Time visited: May/Spring
Don't forget to pack:
Sun Hat & Umbrella (I boiled in the heat and got caught in the rain during this trip)
Lactaid for my very lactose-intolerant family
Foldable reusable bag
Travel
If flying, explore your options to discover whether Midway or O'Hare will be a better price airport from your point of origin
For my grandparents with limited mobility, a direct flight is preferred, and they arrived and departed via Midway. They can navigate a layover with the help of my uncle, but it's easier for all involved if they can nab a direct flight!
For my brother and sister-in-law, a 5-hour roadtrip from a neighboring state is doable for them. They love Chicago and to them it's worth the drive.
For myself and my partner, we flew with one connection through our nearest hub (Atlanta) into Midway airport.
Day 1 - Friday
10pm - Arrival via Chicago Midway Airport and check in to our Airbnb (South Loop area)
11pm- Late Night Dinner and Drinks at Shinya Ramen House
After waiting a few minutes and getting mildly sprinkled with rain, we got a table for five and enjoyed the small plates, including edamame and meat skewers as well as a gigantic seafood pancake covered in fish flakes. I enjoyed a refreshing cocktail made with calpico and vodka as well as black garlic tonkotsu ramen. This was such a great late night spot for eating, drinking, and catching up.
Day 2 - Saturday
9:30am- Brunch at Yolk South Loop
"Brunch, party of 9?" The phrase alone gives me anxiety and is one of the complicating factors when you're traveling with family. I searched for a crowd pleasing brunch that would take reservations and was close to my grandparents' hotel, but came up short on options.
Fortunately, my family was entirely on top of it and we all serendipitously arrived when the gigantic table was ready! This place was absolutely delicious and as boisterous as a regular brunch spot should be. Everyone from graduates to grandparents was satisfied by this meal and fueled up for the day. I devoured the classic eggs benedict and split the banana strawberry crepes with my partner.
11am- Exploring
The groups split off to take care of various errands, leaving my partner and I to enjoy an absolutely gorgeous day - blue skies and breezes. We walked around the nearby parks and stopped at the Chicago Public Library (Great place to use the restroom but also go up to the 9th floor for some quiet time in a gorgeous marble room with a ceiling full of windows).
Visited Sweet Bean Café for a black sesame matcha latte with oat milk. I was surprised that the black sesame bits appeared to be floating around on the time, but as time wore on, the sesame flavor melded into the drink for a pleasant savory-sweet effect. We returned to sweet bean on another day as well and I tried the strawberry matcha and savored a black sesame bread-pastry concoction.
1pm- The Shedd Aquarium
I purchased timed entry tickets ahead of time (3-4 weeks in advance). It was Mother's Day Weekend, and I don't take any chances.
For this trip, I focused om choosing activities that had wheelchairs available for use for my grandma, who has limited mobility and is not able to walk long distances at speed. I had never taken my grandparents to an aquarium before, but they loved it. I think it did make them (and me) hungry for seafood.
Although a large chunk of the aquarium was closed off for construction, they still enjoyed it - especially the dolphins and the beluga whales. They also enjoyed pointing at shrimp and asking me questions about different fish. Most of all, they enjoyed the gift shop.
3pm - Lunch-Dinner = Linner at Umai
I couldn't wait for dinner so we stopped at Umai Japanese Kitchen and Sushi, where I had one of the most fatty and flavorful salmon experiences of my life.
6pm - Dinner at MingHin
Our family places an extremely high value on great food, especially the dim sum at our perennial favorite, MingHin. Despite a long wait for our party of 6, it was worth it. The dim sum - and all of the food here was surprisingly light. Many dim sum places feature food that is a lot heavier and oilier in feel, but here the food was light, fresh, and well seasoned.
Har gow (my favorite!)
The dishes we enjoyed most were the stir fried green beans (my sister-in-law vouches that these are even better than Din Tai Fung's, which is high praise!) and the salted egg yolk bun (honestly to die for, I could have one of these every day).
Sauteed green beans with perfect combination of crispy and soft textures
My preferred steamed dishes were excellent - shu mai, har gow, and shrimp crepes were consumed until we were fit to burst.
Wash it all down with hot jasmine tea, and you have some very satisfied Filipino grandparents. We escorted them back to their hotel, then ventured out to explore Chinatown!
8pm - Chinatown
If you have a vehicle with you, do not even bother with trying to park it here. Just take rideshare. Parking is fiercely contested and the lots are extremely small!
There's a big bricked square with statues of all of the chinese zodiac animals which makes for a great photo op - everyone take a photo with your zodiac animal! Or… google what your zodiac animal is and then take a photo with it, haha.
Candy Store - Love stopping in here for novelty flavors of kit kats along with hi-chew and any of your favorites
Matcha En - My sister-in-law's recommendation and her absolute favorite place! After our visit, I can see why. This place stays stacked with customers! Their most popular item is their soft serve matcha ice cream, which you can get on its own or swirled with other flavors and is served in your choice of pastry or in a cup. This was when we were most thankful for the lactaid I packed.
Day 3 - Sunday - Graduation Day! And also Mother's Day
9:30am - Mother's Day Brunch at Eleven City Diner
Great luck and excellent planning prevailed, with our party of 7 miraculously getting a table within a 20 minute wait. Once again, my uncle and grandparents got there early to put our name in and we were able to be seated!
This place has such a cool diner vibe reminiscent of the 50's with plenty of cozy yet zany décor and punchy music.
My partner had eggs scrambled with of veggies and a side of potatoes, while I scarfed down a potato pancake with lox on top and plenty of caper deliciousness. This breakfast fueled the whole family and warded off hangriness at least until dinner!
11:30am Garfield Park Conservatory
Although this was 15 minutes away by rideshare, admission was free! Thanks to me booking our free timed-entry tickets 4 weeks in advance, we were able to get in even on Mother's Day, which I imagine is one of their busiest days of the year.
I chose this place because 1- I love botanical gardens and visit one in almost every city I go to, 2- It was free, and 3- they had wheelchairs available for my grandma.
However, it turned out to be so much more than that! Garfield conservatory has a large indoor area, making it a weather-proof activity and they had a lot of plants that my grandparents were familiar with and actually grow themselves (bananas, calamonsi, and guavas).
One building had beautiful huge birds of paradise everywhere and luxurious mosaic fountains… and a coffee station! We sat down all together, ordered coffees, and enjoyed the atmosphere for a bit.
Most botanical gardens have a "desert room" filled with cacti and a "jungle room" filled with climbing vines and ethereal flowering plants - but this was the first garden I've been to that had an entire room dedicated to ferns! The "Fern Room" was positively dripping in verdant foliage from every single corner, all shapes and sizes from the demure lady fern to the bold staghorn fern! I felt as if a primordial creature was going to pop out at any moment. Koi fish also swam peacefully in the interior ponds. Unfortunately this was the only room that was not wheelchair accessible.
3pm Graduation at the Arie Crown Theater
All I can say is wow, art school graduation was so much more fun than any other graduation ceremonies I've attended!
7pm Family Dinner at Thai Spoon
Rather than a graduation party or formal dinner, we opted for a relaxed meal at one of my cousin's favorite take-out spots.
I could have guzzled a gallon of the shrimp green curry they brought me, and the sushi was generously portioned and fresh-tasting. I enjoyed a thai tea although it was on the sweeter side. For dessert they brought us these gently sweet, warm coconut puddings which were so comforting.
Traveling with family can be a lot, and I'd be lying if I said I wasn't anxious while creating this itinerary. With family, there can be a multitude of competing interests, priorities, and mobility levels, not to mention the complexity of the relationships themselves. However, I am overjoyed with how well this trip went - and it's actually inspiring me and giving me the confidence to plan equally complex family trips - Vegas, San Diego, and more on the docket for our next trips!