How to Have the Perfect Girl’s Weekend in Chicago

The Perfect Girl’s Weekend in Chicago

Rosé All Day in the Windy City

Chicago definitely ranks in my top 5 favorite cities, for a myriad of reasons. I’ve written about going to Chicago for sports before, but this time I tried my hand at another girl’s weekend (and spoiler alert: sports were still involved). Last month I hit up Chicago with two of my girls – Braidee and Shannon and here’s a little more about our weekend trip. 

For starters, getting to Chicago from Houston is incredibly easy with 10 daily flights on United alone. Of course, add in Southwest and Spirit for direct flights and take into account two airports on both sides and you’ve got a city that’s a breeze to get to. 

Stay: Loews Chicago

I’m a sucker for fancy hotels and ever since a recent trip to New Orleans; I have become a huge fan of the Loews properties. Loews Chicago is my pick for a Chicago hotel if you want to be in the center of all the action complete with luxurious amenities, a crowded bar on the regular, spacious rooms (ours overlooked the Navy Pier, which was awesome for my friend Braidee who had never visited Chicago before) and a walkable atmosphere with stuff in every direction. Lowes Chicago is located in Chicago’s Streeterville neighborhood, only a few blocks from all the fun shopping at The Magnificent Mile. The hotel is in the heart of downtown, one block from the Chicago River and made the perfect place for our girl’s weekend (start your day with coffee in your room or Starbucks in the lobby, order breakfast in bed from room service because their food is amazing, grab a cocktail before you head out for the night, work your booty off at the gym and more). 

Loews Chicago was just a $30 Uber ride, but if you’re balling on a budget or want to experience the

Loews Hotel Chicago: Luxury Hotel

 city like a local, you can also take the ‘El’ Train for $2.50. These were the directions from the concierge (I always call and get directions if taking public transportation because my navigation skills are severely lacking!): From baggage level, follow “Trains to the City” signs, then exit STATE/LAKE, about a 45-minute ride. Walk a few blocks to Loews Chicago and your vacation is ready to begin. Trains depart from the airport every 10-15 minutes, making it a breeze.

We arrived to the hotel just in time to start the evening with handcrafted cocktails from The Bellhop Bar in the lobby. It’s a super cute limited-edition pop-up bar inside a retrofitted steamer trunk boasting bespoke beverages, and the ideal way to kick off the weekend (5-7p daily).  

Our Girl’s Trip Chicago Itinerary

A girl’s weekend in Chicago is alwaysa good idea (though if I had to pick a favorite time to visit, it’s the summer hands down). The city has something for everyone including shopping, pizza, nightlife, culture, sports, fancy spas, brunch headquarters – the list goes on.  

We kicked off Friday night at a Blackhawks game. The game day experience in Chicago for any and every sport is unlike any other with some of the most ravenous and boozy fans around. (Another reason I love visiting the summer in Chicago is for a visit to Wrigley, which should be on everyone’s bucket list.) 

After the game, we hopped in an Uber and headed to dinner at Sushi Dokku thanks to a quick Google search that satisfied all three of us. Then we tried our hand at a number of the bars in Chicago’s West Loop neighborhood, since we were already there and each spot had their own vibe with varying music and great people watching. My favorite was the one blasting 80’s music, but if you think I remember the name of that bar that late at night, you’re crazy.  

Saturday morning we tried finding a nearby workout class on ClassPass, but couldn’t get our act together, so we headed to the hotel gym. I loved that they had Peloton bikes, and am always a fan of working out while on vacation – thought it’s not like we didn’t hit 20k steps every day walking around the freezing city. Another favorite outdoor Chicago workout is a run along Lake Michigan, a 20-mile lakefront trail, which is one of my favorite ways to experience any city.

Chicago is Brunch-so–So-Hard Headquarters

Chicago – Brunch so Hard

Then we freshened up for brunch at Beatnik. Brace yourself for Chicago’s brunch scene. I don’t mean to knock Houston, but this city knows how to brunch. Seriously, the brunch options alone are worthy of a visit. Beatnik was an unassuming spot in West Town, but as soon as 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 a bit too intense for my hungover self, but they serve tapas style bites with cocktails available in pitcher-servings and was an Instagrammer’s delight. (Tip: we made reservations for almost every spot the morning of, but reservations are highly recommended.) On the way back, our Uber made a slight detour to snap a few pictures at the West Hubbard Street Murals, which was an entire street with so many murals, a super indigenous way to check out a new part of Chicago I hadn’t visited before. 

No trip to Chicago is complete without a visit to Stan’s Donuts (y’all know I love my donuts) and well worth the calories, since we were off for an evening of ice skating. We went to 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 Chicago bucket list (though the picture is usually best in the daytime). 

Obviously libations are needed after an evening of awkward ice skating (because I was so bad at it, let’s be real), so we walked a few blocks to Cindy’s Rooftop, located inside The Chicago Athletic Association, but be warned – having dinner in the sky comes at a price (and reservations are a must). I also fell in love with cannedroséhere a few summers back, so it holds a special place in my heart. 

After drinks I headed back to the hotel for dinner (the girls went somewhere else, but I had heard the hotel restaurant was the best) at ETA Restaurant + Bar where I had one of the most delectable ribeye steaks and “Mashers.” I am a steak queen and I promise the steak here rivals any Texas steak I’ve ever had. I sat at the bar, because dinner at hotel bars is one of my favorite things while traveling, especially solo. 

Thanks to a late hotel checkout we were able to enjoy a little Sunday Funday. We started with

The Hampton Social

brunch at The Hampton Social, which just opened a new location in Streeterville, walking distance from the hotel. This is where the signature Instagrammable neon-lit “RoséAll Day” sign is. I love “basic brunch spots” and live acoustic music and their East Coast menu make for the perfect Sunday in Chicago – (followed closely by a game at Solider Field). Then we walked over to the Christkindlmarket, which is an open-air traditional European market in the heart of downtown, which was fun to see but not really my thing, then more shopping on Michigan Avenue followed by one farewell glass or roséat Eataly. If you’ve never been to an Eataly before, you should go. What a novel concept – genius in fact. 

One of my favorite blogs is based in Chicago and they also wrote a Chicago City Guide. 

I also wrote about 48 Hours With the Girls in Chicago for Houstonia Magazine.