Your ideal 48 hours in Chicago

A city close to my heart, Chicago is an amazing spot for a weekend escape, especially during the summer. It offers an incredible variety of attractions—food, drinks, deep dish pizza, rich history, stunning architecture, efficient public transport, legendary sports teams, lively festivals, vibrant music scenes, museums, beaches, and an astonishing shoreline trail along Lake Michigan… as SNL’s Stefon would say, “This place has everything…”

There’s a lot to consider, so I’m here to highlight some of my top picks: the good news is, whatever you miss on this trip can be saved for your next adventure. As if you’d need an excuse to come back!

Chicago Weekend FAQ

• When to arrive: Aim to arrive on Friday. If you prefer a smoother journey, steer clear of rush hour (between 3 and 7 PM).

• How to get from the airport: Whatever you do, DO NOT – I repeat, DO NOT – take a car. The Kennedy (I-90) is perpetually congested unless it's very early or late at night, and sometimes even then. Instead, take the L, which is part of Chicago's public transit system – the Blue Line from O’Hare or the Orange Line from Midway. The journey takes about an hour and costs between $3 and $5, depending on your destination.

• Getting around town: Speaking of transportation, try to use the L whenever possible. Some neighborhoods may seem close but can take a frustratingly long time to reach by public transit. In those cases, consider using Divvy bikes or calling a Lyft or Uber.

• Where to stay: Chicago boasts an abundance of fantastic neighborhoods. The West Loop features trendy, affordable spots like the Ace and the Hoxton, while luxury hotels along Michigan Ave offer stunning views and easy access to the lake. For what I consider one of the best hotels in the city, book a stay at the Park Hyatt. It encapsulates everything I love about Chicago! More on that later.

• What to pack: Given Chicago's extreme climate, prepare according to when you're visiting. This summer, I opted for light pants, dresses, jeans, and a skirt. The overall atmosphere is casual, so T-shirts are suitable in most places. If you plan on walking a lot, don’t forget your comfiest shoes.

Friday

Arrival: After an hour-long ride on the L from O’Hare, we strolled a few blocks to check into the Park Hyatt Chicago. I had given them a heads-up about my arrival (the perks of this job!) and was delighted to receive a luxurious Lake Michigan suite at a fantastic discount.

Checking in: The suite is stunning, offering unobstructed views of the lake and the Water Tower. The living area features a cozy L-shaped couch, a window seat, a wet bar, and a flat-screen TV, along with a full bathroom off the foyer. The bedroom boasts the same view and window seat, an incredibly comfy bed, and an open-plan bathroom. The free-standing tub elevated the experience even further. My travel buddy and dear friend Claudia and I might have gone a little overboard—we found ourselves exploring every corner, exclaiming about all the fantastic amenities (Pre-batched cocktails! Bath salts! Le Labo products! Chromecast!). It was like kids in a candy store, I swear.

Al fresco cocktail hour: After celebrating our luck with some Cava and continuing to be in awe of our gorgeous room, we made our way to the hotel’s outdoor terrace bar, NoMI

, where we enjoyed gin martinis, delightful service, and friendly fellow patrons who enthusiastically recommended the sushi: the ambiance screamed “this is summer.”

Dinner: We began our culinary journey at Mi Tocaya Antojería in Logan Square (we took an Uber to get there), created by chef Diana Dávila. Originally from the Chicago suburbs, she started working at her parents' taqueria at just 10 years old. Her expertise and passion are evident the moment you step inside. We opted for the outdoor patio (thanks to the lovely mid-70s weather) and eagerly watched the delicious dishes being served. We enjoyed a Paloma and a classic Margarita, both perfectly crafted. Then we ordered an array of dishes—because research—and not a single one missed the mark:

• Guacamole with muddled garlic, serrano, fresh lime, sea salt, and chile ash

• Grilled Spanish octopus with clam salsa coctelera, avocado wedges, radish pico de gallo salsa, and dill

• Hand-pressed corn tortilla filled with Chihuahua cheese, nopales, red onion, tomato, lettuce hearts, and cured cactus salsa

• Heirloom dual Oaxacan masa tetela (empanada) filled with LA blue crab, spring onion, poblano chile, and queso suizo (Swiss cheese) with chicatana chintextle (smoked chile paste)

• Hand-smashed fried black beans

• Heritage Farm 1-year-aged queso fundido (melted cheese with chorizo) served with goat birria, hand-pressed tortillas, consommé, onions, and cilantro.

Can we go back right now, please?

After dark: Chicago boasts a vibrant, modern cocktail scene, exemplified by an old favorite, the Violet Hour, one of the pioneers of this culture. Since I had already visited, we decided to follow a recommendation from my Chicago colleague and check out Billy Sunday (which also has a second location at the Optimist Food Hall, close to our colleagues in Charlotte, North Carolina).

Billy Sunday is just a 10-minute stroll from Mi Tocaya. Be sure to try one of their vintage cocktails crafted with aged spirits, such as the Vintage Amari Daiquiri. I also highly recommend the Billy Sunday Negroni, and if you’re in the mood for something extravagant, go for the $60 flight of Chartreuse.

Saturday

Morning and breakfast: Chicago. Another beautiful, sunny day, ideal for exploration.* The sunrise over Lake Michigan is truly breathtaking—make an effort to witness it.

After enjoying a pot of room service coffee (is there anything better?), we jumped into an Uber to East Ukrainian Village for breakfast at Kasama, a Filipino bakery that transforms into a Michelin-starred restaurant by night. Once a hidden gem, “The Bear” catapulted it to fame. Good for them, but not for us. We waited—I'm not joking—in a line of over a hundred people for two hours and twenty minutes, just to order two egg sandwiches (with cheese and hash browns), a Longanisa sausage patty, a blueberry muffin top, and a cinnamon bun, and we were finished in under 20 minutes.

What I learned: Next time, I’ll order the sausage sandwich and a side of hash browns, pre-order online, and pick it up at the designated time. The only drawback is that you can’t sit inside the restaurant or on Kasama’s charming outdoor patio. However, they do have some benches outside that would have worked for us had I known about them.

Since then, many The Bear fans have asked if the wait was worth it. Yes. Would I do it again? Absolutely not. Did I savor every delicious bite? Definitely yes. The staff was incredibly friendly and fun, which helped ease the pain of the wait.

*Chicago is a deceitful city. When the weather is perfect, like it was during this enchanting weekend, you forget it only lasts about 30 days a year. The rest of the time, it's either a sweltering heat dome with 100% humidity or a frozen tundra with icy snow pelting your face (hard). Don’t be fooled. I see through you, Chi-town!

How to spend the day (including lunch): After the breakfast adventure, lunch was only two hours away. The walk to Pequod’s for deep-dish pizza was just over a mile, which we definitely needed, so we strolled over. We also ordered a salad—gotta keep it healthy! The waiter informed us that the pizza would take about 45 minutes, but it arrived in closer to 20, and the melty goodness brought us immense joy. It felt like a crime to only have one slice each.

Following lunch, we made our way back downtown to enjoy the Chicago Architecture Center’s boat tour. This 90-minute journey offers a crash course in modern architecture intertwined with the city’s history. You’ll learn about architect Ludwig Mies van der Rohe—his 1970 IBM building is now the home of the luxurious Langham Hotel.

Dinner: We hopped in an Uber to the West Loop for dinner at the Publican in Fulton Market. The atmosphere is lively, boisterous, and delicious—think “Eastern European beer hall.” The Publican takes pride in sourcing ingredients from local producers, showcasing them on the menu. It’s eclectic and vibrant—a little gem salad is given a salty twist with fried pig’s ears. Don’t miss the oysters, and be sure to try the breads and spreads; there’s nothing quite as simple and perfect as fresh bread and butter.

After dark: While friends were enjoying themselves at the trendy Z Bar at the Peninsula, we opted for a more relaxed Cognac nightcap at Bisous, a touch of Parisian chic also located in Fulton Market. We were struggling to stay awake after a day filled with eating, walking, and touring. Thank goodness for the most comfortable bed ever at the Park Hyatt.

Sunday

Morning: Another beautiful sunrise accompanied by a pot of room service coffee before our early adventure. No trip to Chicago is complete without a stroll (or jog or bike ride) along the Lakefront Trail. It's definitely worth braving the weekend crowds for the stunning skyline and waterfront views, plus the fantastic people-watching. Early mornings or evenings are ideal, especially on warmer days.

How to spend the day: Having hit our step goal before 10 a.m., we headed straight for breakfast at Lou Mitchell’s in the West Loop (it also gets a quick nod in season 3 of The Bear). Any place that treats its waiting customers with donut holes has my vote. This beloved local gem draws crowds for its affordable prices, friendly service, and delicious diner classics, both sweet and savory. My favorite is the corned beef hash, though the silver dollar pancakes are always a hit.

Whenever the Cubs are playing at home, I make it a point to catch a game at Wrigley Field. In my view, nothing embodies Chicago more, and it’s the perfect way to wrap up any weekend getaway. Grab bleacher seats to enjoy a Chicago dog from Hot Doug’s (now sadly no longer a storefront, much to the dismay of the entire city).

Goodbye, Chicago: After the game, we meandered around and shared one last beer at The Cubby Bear in Wrigleyville before collecting our bags and taking the L back to O'Hare. Leaving was tough (I would have added an extra day if possible), but we bid a heartfelt farewell to Chicago—it truly is my kind of town.