My heartstrings tether to Chicago. Occasionally one will tug, and soon enough, I’m planning another weekend trip out there. The city is in my blood, as my dad spent his early adolescent years in Chi-town, playing basketball on the streets and sneaking out to the L past curfew. He was excited for me to discover the city for myself. And I have, over and over again. Out of all the seasons, summertime in Chicago is my most favorite.
My most favorite season to explore Chicago is in the summer. It can be miserably hot, but this season brings out some of Chicago’s finest qualities. Lake Michigan provides the sweltering city respite in the months of deep summer; the Cubbies breathe spirit into Wrigleyville; Navy Pier awakens and glitters with activity; parks supply a community of food festivals and movies under the stars. It’s Americana at it’s finest, something the Midwest does very well.
Last summer, Phil and I spent a long weekend in Chicago. We made it a summer tour, engaging in some tourist activities we sometimes avoid. The first night’s sunset was spent on an architectural boat tour of the city- floating along the Chicago River to the city’s boasted architecture and making our way out onto Lake Michigan. The city lights grew smaller the further we drifted onto the great lake, and soon the boat was full of photographers trying to get the perfect shot of that classic skyline at night.
The next day we spent a melty afternoon in Wrigleyville touring the Wrigley Field grounds, sitting in hot-to-touch bleachers, the Cubbie dugout, and press room. After an hour, you start to feel quite at home in this quaint ball field. We were in the dugout when the sprinklers turned on, making the tss-tss-tssss sound, just like it does in the neighborhood. I had this strong urge to take my shoes off and go running on the thick green.
But I didn’t – security wasn’t called, and the tour ended on time with little dramatics. Instead, we made our way to lunch, a few steps from the ballpark to Big Star. It’s an open-air space during the warmer months, serving some extremely tasty tacos and juicy margaritas. I hadn’t had a taco like this since the last time we were in California! The ingredients were fresh, simple, and so delicious, from the bright salsa to the warm corn tortillas hand-made daily.
The melty day eventually turned into simmering dusk. We made our way along the Navy Pier, with views of a sherbet-colored sky settling into the night. The water was shimmering, the population on the pier bustling, the Ferris wheel glowing, and all the while we were charmed once again with Chicago. Taking a seat on the Pier’s second story, we people-watched and immersed ourselves into the calm spirit a short getaway summons. After night-fall, we were officially touristy-tourists – exhausted and satisfied. Sleep was good that night.
If you haven’t already, I encourage you to see for yourself what a summer in Chicago is like. Read on for my suggestions on what to do, what to eat, and where to stay!
Chicago’s Summer List
Do
- Grant Park: Millennium Park and Cloud Gate (aka The Bean), Buckingham Fountain, Maggie Daley Park
- Wrigleyville: Wrigley Field Tour
- Lake Michigan: Oak Street Beach, North Avenue Beach, Navy Pier, Lakefront Trail
- Chicago River: Chicago Riverwalk, boat tours
- Rain Check: The Art Institute of Chicago, The Field Museum, Shedd Aquarium, Adler Planetarium
Dine
A good burger: Au Cheval $$ has a moody, clubby feel with plush leather booths and cheeseburgers so delectable some claim as the best burger the city has to offer.
An Italian dinner: Piccolo Sogno $$$ features both rustic and modern Italian fare with beautiful outdoor seating and a well-curated, exclusively Italian wine list.
A trimmed-up Chicago slice: Spacca Napoli $$ serves pizza made in a wood-fired oven with mostly imported Italian ingredients. And no, it’s not blasphemy to eat Neapolitan style pizza in Chicago…it’s naaaht!
Stay
Longman & Eagle $: This six-bedroom inn gives off cool, fresh, and approachable vibes. Situated in Logan Square, the inn nestles above a restaurant carrying the same name. Your room may not be the quietest the city has to offer, but it may be the coziest. Inspired by the city’s history centered around a community found in pubs, you’ll feel like you’re in a place where everyone knows your name. After a long day of walking in the park, rest your weary feet at the inn’s restaurant. Have a pint with dinner. Then walk up a set of stairs, and put yourself to bed.
Chicago Athletic Association $$: A lot is going on here, but in short- this place is fun. The style is vintage athletic/collegiate- the decor masculine-leading, but with feminine touches. Stepping inside, you feel as if you magically belong to an exclusive club. The staff is very cordial and excited to show off all there is to explore- which is a lot. This place boasts of
- a Game Room (bocce ball, anyone?)
- a Shake Shack on the ground floor (which should be a requirement for any decent hotel)
- a coffee shop tucked inside the entrance
- a beautiful lobby that one could spend hours in (complete with bookshelves, cozy stone fireplaces, and library-inspired seating/lighting to get work done between the entertainments)
- Cindy’s- the cherry (literally) on top. It’s rooftop dining with an indoor/outdoor space featuring a fantastic view of Chicago’s park collection and lakefront. Even if you’re not staying here, Cindy welcomes all. It’s worth a visit!
Ace Hotel $$$: If you’re looking for a little extra in your stay, let me suggest the Ace Hotel. In Chicago’s West Loop, this warm but minimalist style is perfect for a summer stay. It’s playful with Chicago architecture highlighted in its design. Clean and elevated. Masculine and feminine. Another little nugget- they work with several community organizations that assist young aspiring artists and writers in their pursuits. Very cool in my book.
Inspired Itineraries
A Summer Day in Wrigleyville: Before heading out to the ballpark, grab some breakfast at the Little Goat Diner. Settle onto the shaded patio or rooftop and dig into some diner classics with a twist from (Top Chef’s) Stephanie Izard, like PB&J Pancakes (yum).
Head to Wrigley Field to explore the home of the Chicago Cubs. Seeing the ivy wall in person is a delight, and the official tour takes you everywhere, including the Cubbie locker room. After feeling the heat in Wrigleyville, you’ll be ready for some refreshing drinks and delicious tacos at Big Star. Filled up on taco fare, you might need an afternoon nap. Swing by Garrett’s Popcorn on your way back home. Stocking up your room with local snacks is a must!
A Summer Evening at the Pier: Reserve an alfresco dining table, under the shading of trees and lemon-colored umbrellas, at Piccolo Sogno. You will find a well-thought-out and seasonally-fresh Italian plate, along with a perfectly paired Italian wine—cue the summer crickets and a little Louis Prima, per favore.
Sticking with the Italian spirit, take a 10-minute stroll south to BomboBar for gelato. My eye is on the Berry Cobbler or Charcoal Oreo. With dessert in hand, make your way towards the Navy Pier for sunset under the Centennial Wheel.
“Eventually, I think Chicago will be the most beautiful great city left in the world.”
Frank Lloyd Wright
The summer of 2020 has looked different for both travelers and locals of Chicago. Navy Pier is closed until the spring of 2021. The Cubs play to an empty Wrigley Field. Restaurants and other businesses are hurting.
But I’m encouraged when I see people rallying and making changes to help the community during this time. I encourage you wherever you are, to support your local business. The dust will settle, Navy Pier’s Centennial Wheel will turn back on, and the doors of Wrigley field will open to fans again. Until then, we need our local business to hold on tight.
Stay safe,
A Note: Our current situation brings more challenges for travel. The following itineraries may be altered due to pending or change in operations. The pandemic should be taken seriously, with caution and respect. Please follow your state and local guidelines during this time. We are all experiencing a standstill in some of our planned adventures. But we shouldn’t pause dreaming up escapes for the future. Just remember, this too shall pass. Let’s inspire and dream and plan.
