Experiencing beaches, breezes, and glorious sunsets in Chicago, Illinois

It was the start of a busy week, and I already knew I was going to need a weekend away. That’s how, on a Monday at lunch, I found myself scrolling through airfare sales while munching on carrot sticks. When I caught sight of a round-trip deal to Chicago, I nearly knocked over my fourth cup of coffee in my haste to grab my credit card.

Chicago is one of my top cities, and Jen—a friend of mine who lives there—is always down to host. She’s someone you can always count on to be down to grab a drink and chat for an hour or two—or eight. Even better, she lives in the center of a killer cityscape, surrounded by award-winning museums, creative restaurants, and idyllic beaches. Chicago is infinitely more than its sports teams and shopping, though I love those, too.

An easy welcome

Getting to the Windy City—located in America’s heartland—was a breeze. I flew into O’Hare and hopped on the L train to beat the city traffic to meet Jen at her home in Logan Square.

The L, short for “elevated,” is an electric railway that zips through and around Chicago’s older districts and towering skyscrapers. The train rolled by ornate turn-of-the-century brick row homes and sleek 21st-century condos, passing the city’s many restaurants, shops, museums, and parks, offering a new view at every turn.

After a brief reunion at Jen’s apartment, we headed out. Historically we’ve had my welcome-to-Chicago dinners at Pub Royale, a lively Wicker Park restaurant and bar serving Anglo-Indian fare. As much as I love a new spot, I’m also a creature of habit. Pub Royale is one of my favorites, and Jen is game every time.

As we happily munched on gobi Manchurian, samosas, and curries and sipped our way through each of the bar’s four takes on a Pimm’s cup, Jen regaled me with her breakdown of all the new food and drink spots Chicago has added.

First on my list to try was The Up Room at The Robey, so we headed there next. This 13th-floor rooftop lounge boasts great skyline views. At night it offers a dark, sophisticated atmosphere that seems to encourage patrons to sink into plush, mid-century-inspired sofas, sipping an Old Fashioned. Jen and I shared one before calling it a night.

The Midwest’s best

Jen and I started the day early with breakfast at another Chicago favorite, Bang Bang Pie Shop. Despite the name, we went for the biscuits—fluffy, buttery perfection served as a breakfast sandwich or simply with toppings. We planned to carb up before a day of napping in the sun.

After a leisurely breakfast, we hopped back on the L and headed to the award-winning used bookstore Myopic Books for our beach reads.

Not everyone knows Chicago is a great beach town. The city is perched on the edge of Lake Michigan, one of the largest freshwater lakes in the world. Sometimes dubbed America’s Third Coast, the lake stretches farther than the eye can see, rippling gently with waves on good days and raging with squalls on stormy ones. Soft white sand is plush under bare feet, while breezes over the water help Chicago residents cool off from summer’s heat.

The beaches also offer prime views of the downtown Chicago skyline. Our favorite is Oak Street Beach, lined by historic hotels like The Drake and icons like the Willis Tower (popularly known as the Sears Tower).

Oak Street Beach was busy, but not too crowded. We easily found a spot and settled down. Minutes turned into hours of idle reading, chit-chat, book exchanging, and people watching. I dozed off every now and then, lulled by the sounds of nearby laughter and the warmth of the sun competing with a cool breeze to keep us perfectly temperate. I startled awake after one such catnap to find Jen dusting off her blanket.

“The sun’s going to set soon,” she said.

I couldn’t believe how quickly the time had passed. We packed up and headed back toward the city in anticipation of the shows we’d planned to see.

A weekend’s twilight

Our next stop was North Michigan Avenue. The building formerly known as the Hancock Center, now nameless, offers box seats to the natural artistry of Midwestern sunsets.

Light bounced off the glass panes of Chicago’s skyscrapers into a spectacular finish.

As the sun lowered slowly to the horizon—a long journey in these flat landscapes—light bounced off the glass panes of Chicago’s skyscrapers into a spectacular finish. Locals with guests and travelers-in-the-know grabbed cocktails at the building’s Signature Lounge about an hour before dusk in preparation of toasting the end of the day. On a particularly good night—like this one, with an exceptionally fiery scene—the audience breaks into applause once the sun slips from view.

Following nature’s presentation, we went to a mainstage comedy show at Second City, the comedy club where legends including Bill Murray, Dan Aykroyd, Tina Fey, Amy Poehler, and Steve Carell launched their careers. The comedy didn’t disappoint, and by the time we wrapped up the evening, all of the workweek stress I’d been trying to escape had fully melted away.

Sunday was the beginning of the end of my weekend away. Jen and I wanted to make the most of the remaining hours, so after I packed, we went back downtown.

Stopping first for a coffee and breakfast at Intelligentsia, we made it to the Art Institute of Chicago just as the doors opened. We walked the museum’s serene halls, admiring one of the oldest and largest art collections in the country.

Afterward, we soaked in a bit more of the outdoors—and each other’s company—with a walk along the Chicago Riverwalk.

It’s always hard letting go, but there’s no question I’ll be back again soon—to see Jen and one of my favorite cities. And next time, I’m not waiting for stress to build up!

Start planning your trip to Chicago.

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