Chicago may be my new favorite city to visit. It’s a cheap, short flight to two different airports or an easy 7-8 hour drive from Nashville. It’s big (2.7 million) without being overwhelming (like the 8.4 million of NYC) and each neighborhood offers a whole new vibe. The summer weather is less humid than home but still hot and appropriately summery. It’s a progressive and diverse town, with a vibrant LGBTQ+ scene, legal recreational weed, and reliable public transit. Eating out is not as insanely expensive as you might assume and every kind of food you could desire is available. The architecture is endlessly interesting, and there are museums for every predilection. You can quickly escape the hustle and bustle of the city at any one of the myriad public parks, beaches, or lakefront activities. You really get the best of both worlds: modern urban convenience and beautiful outdoor scenery.
I’ve had the pleasure of visiting this city several times, for work and for leisure, to visit friends and or just for the heck of it. We got to attend the after party of a Polish wedding and see Wayne Brady as Aaron Burr in Hamilton. The most recent visit came about because we were able to arrange a home exchange for the exact week of our son’s summer break. Since we both work remotely, neither of us had to take off too many days from work. We drove up on a Saturday and back the following Saturday, staying in an apartment in the lovely uptown residential neighborhood Buena Park. We explored the uptown area a bit, visited my bestie up in Edgewater, and even walked through a live film set!
Buena Park didn’t offer as many restaurant options as we would have liked, but the proximity to the parks, walking path, and beach was so great. We had such a lovely time this time around, despite our kid coming down with pneumonia, plans getting canceled, and the trip ending a skosh earlier than planned. We ate a lot of good food, went out with my coworkers for an adults-only night, watched the Navy Pier fireworks from the comfort of a friend’s downtown deck, and walked A LOT.
With so many local friends, we hope to return many times in the coming years. It happens to be a good midway point for visiting the Husband’s family in Sioux Falls, so maybe one day we can convince them to meet up and explore the city with us? 😉
What We Explored
Lincoln Park Zoo. I have never been to a zoo like this one before! There’s no main entrance because it’s free and is just part of the park. The lush scenery was so beautiful! The zoo is split into three different sections, each one well laid out and worth seeing: the farm (though most exhibits were closed), the nature boardwalk, and the rest of it. Their variety of animals was pretty decent, considering the cost and size of the zoo — heck, we even saw an animal I’d never heard of before! A Takin!– so even though we were disappointed that the big cats exhibit was closed for renovation, we still got to see tons of birds and reptiles, flamingos, a polar bear, zebras, rhinos, giraffes, and a two-humped camel. The real highlight for me was the primate house, where we saw monkeys, lemurs, sloths, and gibbons and African Apes center, where we saw chimps and gorillas in massive, indoor naturalistic exhibits. If we lived in Chicago, I know we’d spend a lot of time walking through this zoo!
Montrose Beach. A 25-minute walk from our apartment, this massive park and beach would be a place we spent a lot of time if we lived in this part of Chicago. So much space for activities! We witnessed tons of parties and grill outs — people legit carried grills to the beach for big family cookouts. Yoga classes, kids playing soccer, birthday parties, we even saw one dude taking a massive hit from a bong. The beach may not be what a Floridian like myself thinks of when you hear the word but it’s quite nice for a lake beach. The blue of the water reminds me of the Caribbean, and the sand was softer than I expected. Overall, a very clean, easy beach with a solid dining option and plenty of restrooms and outdoor showers.
Maggie Daley Park. Holy moly, if we’d had anything like this when we were kids, I know my brother and I would never have wanted to leave! I can’t believe it’s free. We could have spent hours here if Skyler were older and able to enjoy more parts of it; we really just hung out in the main section (which says its for 5-12 year olds, whoops). Definitely worth the trek downtown to visit! If you have kids, you won’t want to miss this amazing playground.
The Bean. Even though we’ve been there done there, we couldn’t *not* check it out. I knew Skyler would love it.
Riverwalk. A lovely way to stretch your legs and take in the city! Sitting at a little outdoor dining spot, letting Skyler play with a giant connect for and my husband have a drink, it reminded me of Paris a little bit: watching all of the water taxis and river tours driving by, the buildings juxtaposed against the water (though this water is WAY nicer than that of the Seine).
Public transit. This was Skyler’s and my first time riding the trains in Chicago. He was not impressed but did enjoy watching the doors open and close. For me, it was kind of a big deal since I’ve really struggled with anxiety around public transit for a long time. I think the trains mostly being above ground really helped make it less nerve-wracking.
The ‘burbs. We’re lucky to have friends who live here, and we spent a fabulous afternoon hanging out with them, their parents, and their kids. We could not have asked for better weather, and I got to hang out with my best friend from college. Definitely a Sunday Funday to remember!
Food and drink. Great big flavorful tacos at Flaco’s Tacos. Late afternoon appetizers and drinks at Francois Frankie. A quick mid-walk respite at Island Party Hut on the river. Dinner at La Josie and classic cocktails at Moneygun. Upscale American at Beatrix. Pizza from Michael’s. Al fresco seafood at The Dock. Upscale American fare at Beatrix. We really didn’t have anything bad or disappointing.
What We Skipped
Navy Pier. We’d both done Navy Pier in the past and didn’t feel like rehashing it.
Magnificent Mile. Neither of us care about shopping when we travel. It’s just a giant mall.
A baseball game. We saw a game at Wrigley back in 2013. Why repeat? (Clearly, I’m not a sportsball person.)
Museums. We have a 2.5 year old and the weather was perfect to be outside. We opted to spend the days we had out doors or visiting friends.
Tall building look outs. While I am a sucker for an urban vista, I’ve already done the tilt experience at the Hancock building and the Willis Tower SkyDeck. I wanted to see new stuff this time!
What We Want to Do On Future Visits
The Aquarium, MOSI, Art Institute of Chicago, the Field Museum, some sort of riverboat or water taxi, see a show, spend more time at the beach, hang out in Wicker Park or Logan Square, go to a neighborhood block party, stay for more than a week.
What are you favorite things to see and do in Chicago? What should we do next summer? Where are the best toddler-friendly spots in town? Which neighborhood should we stay in next time?
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