No matter when or what your travel style, Chicago is always a good idea for a girl’s trip. With a plethora of festivals, parades and sporting events to choose from, you’ll never run out of things to do here.
My friends and I planned our recent weekend arrival perfectly, starting Friday evening with handcrafted cocktails from The Bellhop Bar in the Loews Chicago lobby, an adorable pop-up bar retrofitted from a steamer trunk packed with bespoke beverages on display in the lobby, and the ideal way to kick off the weekend.
Loews Chicago is the place to be for a girl’s trip to Chicago, even in the winter—it’s located in the heart of downtown, one block from the Chicago River with rooms overlooking the famed Navy Pier. It has an on-site luxury spa, a state-of-the-art fitness center, and a noteworthy restaurant. It’s also mere blocks from shopping at The Magnificent Mile.
Getting to the Loews is as easy as the quick flight from Houston. You can jump in an Uber for about $30 or experience the ‘El’ train for $2.50 per person. From the baggage level, follow the “Trains to the City” signs. The train departs every 10 to 15 minutes, then exit at State/Lake. It’s about a 45-minute ride. Walk a few blocks to Loews Chicago and your vacation is ready to begin.
On Friday night, we were off to a Blackhawks game. Even if you’re not a huge sports fan, the game day experience in Chicago is unlike any other with some of the most ravenous and boozy fans around. Then we hopped in a quick Uber for dinner at Sushi Dokku, which was a happenstance decision that resulted in delicious food and drinks, before bar-hopping in Chicago’s West Loop neighborhood.
Saturday morning we tried to find a nearby workout class on ClassPass, but couldn’t get our act together, so we opted for the hotel gym. The gym was busy, but had plenty of space with state-of-the-art equipment, especially the Peloton bikes (not like we didn’t get in our steps walking around the city, but a morning sweat sesh is always a good idea on vacation). Another favorite workout in the city is a run along Lake Michigan, which is a 20-mile lakefront trail frequented by avid runners.
Then we freshened up for brunch at Beatnik. If you haven’t experienced Chicago’s brunch scene, brace yourself. The brunch options alone are worthy of a visit. Beatnik was an unassuming spot in West Town, but once you walk through the revolving doors, an amped up DJ with a brunch spectacle straight out of Sex and the City awaited us. It was an intense scene, and Instagammer’s delight, with tapas-style bites and cocktails available by the pitcher. (Pro tip: we made reservations for almost every spot the morning of, but reservations in advance of that are highly recommended.) On the way back, we made a slight detour in our Uber to snap a few pictures at the West Hubbard Street Murals, which was such a fun way to explore a different part of the city.
No trip to Chicago is complete without a visit to Stan’s Donuts (multiple locations to choose from) and well-worth the calories, since we were on our way to spending the evening ice skating. We met up with some friends at the Millennium Park McCormick Tribune Ice Rink, which was only $15 (free if you bring your own skates), and you can knock a picture at the Bean off your bucket list.
Of course libations are needed after an evening of awkward ice skating, so we walked a few blocks to Cindy’s Rooftop, located inside The Chicago Athletic Association, but be warned—having drinks in the sky comes at a price (and reservations are a must). After drinks we headed back to the hotel for dinner at ETA Restaurant + Bar for a delectable ribeye steak and mashed potatoes (or “Mashers” as the menu calls them) that rivals any Texas steak. ETA boasts a super casual vibe with upscale food and a wine and cocktail list to match.
Thanks to a late hotel checkout we were able to maximize Sunday Funday. We started with brunch at The Hampton Social, which just opened a new location walking distance from the hotel. This is the signature Instagrammable neon-lit “Rosé All Day” sign. Live acoustic music and its East Coast menu make for the perfect Sunday in Chicago—and if you can make a game at Solider Field, you absolutely should.
Then we walked over to the Christkindlmarket, which is an open-air traditional European market in the heart of downtown that runs from mid-November to Christmas Eve, then more shopping along Michigan Avenue followed by one farewell glass of rosé at Eataly.
From Houston, Chicago is one of the easiest getaways imaginable. United alone offers 10 daily flights from George Bush Intercontinental Airport to O’Hare, so it’s a breeze to make the two-hour-and-30-minute flight to the Windy City, with two airports on each side to choose from.