I had the best time in Chicago the weekend before Memorial Day! I’ve been to Chicago five or six times over the years, and it’s always been one of my favorite places to visit. I would totally consider moving there if the weather wasn’t so cold. Because of this opinion, it’s unsurprising that I advise visiting in the summer months if possible—the city really comes alive when it’s warm out. That being said, I went in May, which I thought would be warm, but on the day I landed, it was 44 degrees. Luckily, it warmed up to 70 for the rest of my trip, but if you want guaranteed warmth, July and August are the move. The good news is that if you do find yourself in Chicago during the brutal winter months, there are so many activities to do inside, so you’ll still have a great time.
Unlike past recent visits to Chicago, which were for work trips, bachelorette parties, and weddings, this trip was the first one where I had a lot of control over the itinerary since it was just for a good old fashioned girls’ weekend. I’ve known my friend Jackie since the ninth grade, and we became fast friends as we both stressed about grades, AP classes, and questionable boys together on the regular. We went to UVA together and have kept our friendship strong throughout adulthood, always making an effort to catch up with each other even though we haven’t lived in the same city since graduation. Our friendship is one of those great ones where we can easily pick it up wherever we left off, and I had the best time exploring (read: eating and drinking our way through) Chicago with her.
While the majority of the photos in this post are this most recent trips a few weeks ago, I did throw in a few from past trips and also interspersed information on where to stay, what to do, and where to eat and drink from past jaunts to the Second City since I’ve never written a comprehensive travel post on Chicago. Hope you enjoy, and, as always, don’t hesitate to reach out with any questions!
HOW TO GET THERE /
From DC—or any major city really!—Chicago is really easy and affordable to get to. I’ve flown into both O’Hare and Midway, but prefer Midway since it’s smaller, closer to the city, and a bit more manageable. I like to say Midway is the DCA of Chicago and O’Hare is the Dulles if that gives anyone in the DC area who’s less familiar with the Chicago airport scene some good context. Chicago is a big hub for Southwest and United, so I usually try to fly one of those airlines—and often end up on Southwest since their hub is Midway, while United’s is O’Hare. Oftentimes, I can get roundtrip direct flights at desirable times for $200 or less.
Once you’re in Chicago, getting around is super easy—Ubers are abundant, the L is really easy to navigate, and, if it’s not freezing, it’s very walkable.
WHERE TO STAY /
Chicago has so many wonderful neighborhoods that would be awesome to stay in, but if you’re looking for a good neighborhood to stay in to do touristy things or it’s you’re first time to the city and you want something central, I recommend the River North neighborhood, where I stayed this past trip. Jackie and I stayed at the Hotel Chicago, which I would recommend and personally stay at again. It’s a Marriott Autograph collection hotel and the rooms were spacious and clean. It was one block off the riverwalk on the Chicago River, and super close to the port where the architectural boat tours depart from (more on this below!). There were many great restaurants and bars within the surrounding blocks, and it was a short walk to great shopping down State Street.
On past recent trips, I’ve stayed in Lincoln Park—once with a friend and once at a really gorgeous Airbnb for a bachelorette party. It’s such a beautiful neighborhood with lots of shops, restaurants, and bars in its own right—plus it’s got great access to Lake Michigan. Many of my 20s- and 30s-something cousins and friends live in Lincoln Park and it definitely feels more like a place where the locals hang than River North.
WHERE TO EAT & DRINK /
Chicago has a great food scene, and I don’t think I’ve ever had a bad meal in town!
- Hi-Vibe Juicery—I grabbed a green smoothie here on my most recent trip to Chicago before Soul Cycle, and it was delicious. They also have pressed juice and açaí bowls. Sometimes when you’re on a trip you’re just craving food that will make you feel good after indulging, and Hi-Vibe juicery will give you some great fuel.
- Public House—A block away from the Hotel Chicago, I popped into Public House for a solo lunch at their bar and was really impressed. This would be a great spot for a beer-lover, as they have many drafts and some tables even have their own taps. I had a southwestern salad and it was amazing—definitely a step up from your typical bar food.
- Dos Urban Cantina—I loved this place, and not only because my last name is part of their name! Jackie and I ate dinner here one night, and their happy hour goes until 7pm and is available throughout the restaurant, not just at the bar. They had amazing margaritas, and it was a well-decorated space with beautiful branding elements on their menus. The food is more modern Mexican than your classic Tex Mex fare. We both had the chicken tacos and they were delicious.
- Old Town Ale House—This is a famous dive bar across the street from Second City. I absolutely loved the vibe in here—it was very casual, and you could tell by all the art on the walls it has a very storied history. This place is no frills—they have your classic American lagers on draft and very straightforward rail drinks. It is cash only, but there’s an ATM on site if you need it.
- Taureaux Tavern—We ate here for brunch, and their patio was amazing. It was a bit chillier the morning we went, but they had space heaters that made it super comfortable. They also had an awesome playlist going when we were in. I opted for the burger, and it was absolutely wonderful, and had a few mimosas. They serve them in champagne coupes, which I loved—plus they had the perfect champagne to OJ ratio.
- Bub City—Jackie and I posted up here for a rainy afternoon, and split the chicken tenders, fried pickles, and waffle fries. They’re known for their BBQ, and every plate they walked by looked amazing. This was such a fun day drinking spot, and if you love country music like me, you’ll love their playlist.
- Three Dots and a Dash—This is a really fun tropical speakeasy that will make you forget your in Chicago. They specialized in tiki drinks and Polynesian food. It’s located right around the block from Bub City.
- Apogee Lounge—Apogee is a club-like cocktail lounge above the Dana Hotel with amazing views of River North. I usually get wine at most places, but here they had really awesome bartenders, so I had them whip me up a fabulous margarita. They also have a fun cocktail menu of suggested drinks, many of which come in really cool drink ware.
- Pacific Standard Time—PST serves up delicious California-inspired fare in a really Mid-Century Modern space. It really feels like California inside! Our waiter was a bit aggressive, but overall, I really enjoyed our dinner here. Food is meant to be shared family style, and we shared a margherita pizza, pork and shrimp dumplings, farm lettuce salad, burrata, ricotta dumplings, and roasted cauliflower.
- Green Door Tavern—We grabbed a nightcap at this Chicago classic after dinner at PST. This was a really fun dive-bar atmosphere, and we enjoyed watching other customers take their chances with the $5 spin the wheel shots. Basically, the bartender spins this wheel above the bar, and then makes them a shot based on where the wheel stops.
- Big Jones—If you’re looking for southern cooking in Chicago, this is your place! We went in for brunch. They are known for their fried chicken and their biscuits, so I got a biscuit to go with my fried chicken salad. I also ordered their gumbo, but was not a huge fan—I guess that’s my karma for expecting good gumbo outside of NOLA, hah!
- Lou Malnati’s—My favorite deep dish pizza artisans in Chicago! They have multiple locations, but if you’re looking for the your deep dish fix, definitely head to one of these locations.
- The Hampton Social—This is where the Instagram-famous ‘Rose All Day’ sign is! I ate here for brunch on my cousin’s bachelorette, and we all loved the nautical space. Sometimes I feel like places that have really cute decor don’t always have the best food, but that is not the case with Hampton Social—everything we ate was delicious.
- Howl at the Moon Chicago—A super fun dueling piano bar, we went here for my cousin’s bachelorette and had the best time. If you’re going with a larger group, make sure you have a reservation as this place gets packed!
- Billy Goat Tavern—My friend Sheila and I went here in 2014 when I visited her for a weekend after a work trip, and it is such a fun place. Known for their burgers, it’s named after the famous Billy Goat Curse that was put on the Chicago Cubs.
WHAT TO DO /
The best thing I’ve ever done in Chicago is see an improv show at The Second City. Many SNL people got their start doing improv here, and the caliber of talent remains high. Jackie and I saw their show Grinning from Fear to Fear, which was a comedic take on society, politics, and culture today. We laughed so hard! The show is about two and a half hours, with a 15 minute intermission. You’re given a seat when you arrive, so the closer you can arrive to when doors open, the better. You’re also given a waiter, so it’s easy to get drinks throughout the show. On weekends, there is often an earlier show at 8pm and a later show at 11pm. Shows do change over the years, but regardless of what is running, I don’t think you’ll be disappointed!
Another highlight of our trip was taking an architectural boat tour of Chicago. This last trip was the first time I was lucky enough to take one, and I would recommend it to anyone. (Added bonus, there’s a bar on board!) We took ours with Wendella, which is the oldest and most well known operator of the tours. Our guide was awesome and give us so much great historical context about the city. For instance, I didn’t know Chicago was called The Second City because it’s the second iteration of the city after the Great Chicago Fire. This is the kind of thing you could do multiple times because you’d learn something new every time.
I’ve now taken the elevator ride to the top of the Willis Tower twice and really enjoyed it both times. The views are incredible, and it’s a really great way to see Chicago from the top. The famous clear ledges that allow you to see straight down to the street below often have long wait times, so if that’s a priority for you, I’d recommend going at an off-peak time. We didn’t wait in the two hour line for the ledges this past trip, but my previous trip, there was no wait. In terms of other tourist attractions, I’ve enjoyed taking selfies at Cloud Gate in Millennium Park, colloquially known as The Bean, and riding the Ferris Wheel at Navy Pier.
One thing I’ve always wanted to do is walk along Chicago’s Lake Front Trail, so if it’s warm when you’re in town, definitely add that to your list!
I had the best time in Chicago, and hope to get back sooner rather than later—I would love to spend a day on the Lake in the summer and see The Home Alone house. Drop me a note if you have any questions about anything in this guide: firstname.lastname@example.org.
And for a few throwbacks, here are some pictures I took of Chicago back in 2014 when Instagram filters were still very much a thing! I was in town for work, and stayed the weekend with my friend Sheila. It was Halloween and we went out in Lincoln Park. It snowed on our way home, and that was the instant I knew I could never live in Chicago—I need a true fall season!