Any Chicago weekend ought to include a walk (or jog or bike ride) along the Lakefront Trail © pawel.gaul / Getty Images
A city near and dear to my heart, Chicago is the perfect place for a weekend getaway, particularly in the summer. It has so much to offer, it’s kind of bonkers. To name a few: food, cocktails, deep dish, history, architecture, public transportation, legendary sports teams, festivals, live music, museums, beaches and a shoreline pathway along Lake Michigan that beggars belief… as SNL’s Stefon would say, “This place has everything…”
It's a lot to ponder, so I’m here to narrow it down to some of my personal favorites: the great news is, whatever you don’t get to do during this trip is fodder for the next. As if you’d need a justification to return!
Chicago weekend FAQ
When to arrive: Arrive Friday. Try to avoid rush hour (between 3 and 7pm) arrival if you want a less hectic commute.
How to get from the airport: Do not, I repeat – DO NOT – take a car. It doesn’t matter what time of day, the Kennedy (I-90) is always, always clogged unless it’s very early in the morning or late at night – and sometimes even then. Take the L, which is part of Chicago’s public transportation authority – the Blue Line from O’Hare or the Orange Line from Midway. It takes about an hour and costs between $3 and $5 depending on where you’re going.
Getting around town: Speaking of, try to take the L whenever you can. Sometimes, connecting neighborhoods can be close proximally but take a prohibitively long time on public transportation. In those cases, you can use their bicycle share, Divvy bikes, or hail a Lyft or Uber.
Where to stay: Chicago’s cup overfloweth when it comes to great neighborhoods to stay. The West Loop has a lot of affordable, cool-kid brands, like the Ace and the Hoxton, while the luxury accommodations along Michigan Ave offer breathtaking views of and proximity to the lake. If you’re looking for what I would consider one of the best hotels in the city, book the Park Hyatt. It’s everything I love about Chicago! More on that later.
What to pack: Chicago’s climate is extreme, so prepare in advance depending on when you go. This summer, I packed light pants, dresses, jeans and a skirt. The overall vibe is casual, so T-shirts are fine in most places. And if you plan to walk a lot, bring your comfiest shoes.
Friday
Arrival: After an hour-long L ride from O’Hare, we walked a few short blocks to check in to the Park Hyatt Chicago. I’d informed them of my coming in advance (this job does have its perks) and was given a super luxe Lake Michigan suite at a majorly discounted rate.
Checking in: The suite is breathtaking, with unobstructed views of both the lake and the Water Tower. The living area was furnished with a comfortable L-shaped couch, a window seat, a wet bar and a flat-screen TV, with a full bathroom off the foyer. The bedroom had the same view and window seat, an incredibly comfortable bed and an open plan bathroom. A free-standing tub brought the whole thing up a notch.
My co-traveler and close friend Claudia and I may have lost our minds – we were sitting in every chair, announcing all the things we saw and loved (Pre-batched cocktails! Bath salts! Le Labo products! Chromecast!). Kids in a candy store, let me tell you.
Al fresco cocktail hour: After toasting our good fortune with some Cava, and continuing to marvel at how overwhelmingly beautiful our room was, we decamped to the hotel’s outdoor terrace bar, NoMI
, for gin martinis, lovely service, friendly co-patrons who advocated strongly for the sushi: the vibe was “this is summer.”
Dinner: Our first meal was at Mi Tocaya Antojería in Logan Square (we took an Uber to Logan Square) from chef Diana Dávila. Born in the Chicago suburbs, she started working at her parent’s taqueria when she was 10 years old. Her experience and passion shows as soon as you walk in. We sat on the outdoor patio (thanks to the perfect mid-70s temperature) and salivated over all the dishes we saw pass. We had a Paloma and a classic Margarita, both cocktails were on point. Then we ordered a lot – because research – and there wasn’t a single misfire:
Guacamole with muddled garlic, serano, fresh lime, sea salt and chile ash
Grilled Spanish octopus, clam salsa coctelera, avocado wedges, radish pico de gallo salsa and dill
Chihuahua cheese and crusted hand-pressed corn tortilla stuffed with nopales, red onion, tomato, lettuce hearts and cured cactus salsa
Heirloom dual Oaxacan masa tetela (empanada) stuffed with LA blue crab, spring onion, chile poblano 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 and chorizo) with goat birria, served with hand-pressed tortillas, consommé, onions and cilantro.
Can we go back right now, please?
After dark: Chicago has a fantastic, modern cocktail culture as evidenced by an “old” favorite, the Violet Hour, which was one of the first establishments to make it so. Since I’d already been there, we decided to follow a recommendation from my Chicago-based colleague and hit up Billy Sunday (which has a second outpost at the Optimist Food Hall not far from our other colleagues in Charlotte, North Carolina).
Billy Sunday is about a 10-minute walk from Mi Tocaya. Try one of the vintage cocktails made with aged spirits, like the Vintage Amari Daiquiri. I also recommend the Billy Sunday Negroni, and if you’re feeling particularly indulgent and adventurous, opt for the $60 flight of Chartreuse.
Saturday
Morning and breakfast: Chicago. Another special, sunny day, perfect for exploring.* The sun rising over Lake Michigan is quite a sight – try to catch it.
After indulging in a pot of room service coffee (is there anything better)?, we hopped in an Uber to East Ukranian Village for breakfast at Kasama, a Filipino bakery that doubles as a Michelin-starred restaurant at night. Once an under-the-radar local favorite, “The Bear” came along and made it insanely famous. Good for them. For us, not so much. We waited – I kid you not – in a line of people numbering well over a hundred, for two hours and twenty minutes, 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 done in under 20 minutes.
What I learned: Next time I’ll order the sandwich with the sausage and get a side of hashbrowns, pre-order it online and pick it up at the appointed time. The only downside is that you can’t sit in the restaurant or Kasama’s adorable outdoor patio. It does, however, have some benches outside that would have done for us had I known about them.
I’ve since been asked by many The Bear fans whether the wait was worth it. Yes. Would I do it again? Absolutely not. Did I relish every delicious bite? Absolutely yes. The staff was so friendly and fun, too, which took some of the sting off the wait.
*Chicago is a lying liar who lies. When the weather is ideal, like it was this magical weekend, you forget that it’s like that maybe 30 days a year. The rest of the year it’s either a sweltering heat dome with 100% humidity or a frozen tundra with icy snow that pelts your face (hard). Don’t fall for it. I’ve got your number, Chi-town!
How to spend the day (including lunch): The odyssey that was breakfast meant lunch was only two hours away. The walk was a wee bit over a mile, which we needed, so we hoofed it to Pequod’s for deep-dish pizza (featured in another cameo on The Bear). We also ordered a salad – health! The waiter said we’d wait for 45 minutes for the pie to come out, but it was closer to 20, and the ooey gooey goodness brought us such sublime happiness. It was a crime we couldn’t eat more than a slice each.
After lunch, we returned downtown to take the Chicago Architecture Center’s boat tour. This 90-minute experience is a crash-course in modern architecture mixed with city history. Learn about architect Ludwig Mies van der Rohe – his 1970 IBM building is the current home of the 5-star Langham Hotel.
Dinner: We took a quick Uber to the West Loop for dinner at the Publican in Fulton Market. Noisy, boisterous, delicious – the vibe is routinely “Eastern European beer hall.” The Publican takes pride in sourcing ingredients from nearby producers and lists them all. The menu is eclectic and energized – a little gem salad gets a salty jolt from fried pig’s ears. Get the oysters and try the breads and spreads, because if there’s anything more simple and perfect than fresh bread and butter, I don’t know what it is.
After dark: Friends were doing it up at the very sceney Z Bar at the Peninsula, but we demurred and decided on a Cognac nightcap at Bisous, a wee bit of Parisian chic, also in Fulton Market. We struggled to keep our heads up after a day of eating and walking and touring. Thank heavens for the most comfortable bed ever at the Park Hyatt.
Sunday
Morning: Another gorgeous sunrise and another pot of room service coffee before our early outing. No trip to Chicago would be complete without a walk (jog or bike ride) along the Lakefront Trail. It’s definitely worth enduring the weekend bustle for the skyline and water views and the epic people-watching, but going early (or early evening) is a good call, especially on warmer days.
How to spend the day: Having hit our step count before 10am, we made a beeline for breakfast at Lou Mitchell’s in the West Loop (it gets a brief cameo in season 3 of The Bear, too). Any restaurant that plies its waiting patrons with donut holes gets my vote. This no-frills, beloved local spot attracts throngs for its reasonable prices, friendly service and tasty diner fare, both sweet and savory. My go-to is the corned beef hash, though the silver dollar pancakes are a perennial favorite.
If the Cubs are playing at home, I always try to catch a baseball game at Wrigley Field. Nothing is more quintessentially Chicago in my opinion, and it’s a great capper to any weekend getaway. Get bleacher seats where you can devour a Chicago dog from Hot Doug’s (no longer a storefront, much to the collective sadness of an entire city).
Goodbye, Chicago: After the ball game, we wandered around and grabbed one last beer at The Cubby Bear in Wrigleyville before grabbing our bags and taking the L back to O'Hare. It was hard to go (and I would have tacked on an extra day if I could have), but we mustered a fond farewell to Chicago – it's my kind of town.
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