Cheryl Shops

Earlier this month, I took my first flight since the beginning of the pandemic and went home to Chicago to see my mom for the first time in a year and a half—the longest I've gone without seeing her in my entire life. For those of you who haven't flown anywhere yet, the plane trip felt completely safe and drama-free, and seeing my family and friends after so long felt amazingly good. It felt strangely normal to be home, possibly because Chicago felt very "What Covid?!" to me, which was equally refreshing and alarming. So after a few days of quality family time in the 'burbs, we headed downtown for a couple nights in the city. We were happy to see that Michigan Avenue was packed, restaurants and bars were crowded (but not overwhelmingly so), and all weekend long, people were dressed up—maybe that roaring '20s thing is indeed happening. Here's what we did on our weekend in Chicago.

What to do

In non-pandemic times, I usually go home to Chicago two or three times a year: often in the spring for Mother's Day, sometimes in the fall for various weddings or events; and always at Christmas. It's been a long time since I've been there in summer, and I forgot how alive the city can be People who grew up on a coast tend to be surprised by how ocean-like Lake Michigan feels, but it has miles upon miles of waterfront trails (great for a long bike ride) and a bunch of beaches. I grew up going to Oak Street Beach, which is also the closest to downtown, and that's the one we went to on this trip. (North Street Beach is also great.) 

Another must for warm weather in Chicago is an architectural boat tour along the river. The Chicago Architecture Foundation is probably the most legit but also annoyingly uses Ticketmaster, so we just bought tickets for the Shoreline right on Michigan Avenue outside the Apple Store. Our tour guide was super knowledgable, and the 90-minute ride covers a lot of ground, addressing both iconic older buildings like the Tribune Tower and Marina City, plus newer buildings as well, like the new St. Regis (which was designed by a woman, Jeanne Gang!). It's a great way to see the city and get a little Chicago history too. My mind was blown to learn that the Chicago fire was not actually started by Mrs. O'Leary's cow! 

The tallest building in Chicago is the Willis Tower (fka Sears Tower), but I prefer the Hancock Building, which, yes, has an observatory, but, even better, has a bar on the 95th floor. The Signature Room is something I always recommend to people; no matter what time of day you go, the view is amazing, but if you can, get there for the sunset and get the best of both night and day. We had a nightcap there, and since it was the 4th of July weekend, we could see fireworks all over Chicagoland and it was pretty darn magical.

We didn't hit any museums on this trip because the weather was so nice, we wanted to maximize our time outside. My favorite, however, is the Art Institute (and we're kind of bummed we didn't see the Obama portraits),but if you have kids, I highly recommend the Shedd Aquarium and the Museum of Science and Industry, which is 100% worth the trek. And, of course, you don't want to miss the Bean in Millennium Park!

Where to eat & drink

It had been close to 10 years since I'd been to Avec; they recently opened a second, bigger location in River North, and we were lucky to score a reservation. The food was even more incredible than I remembered, and the service was stellar. This is, hands down, one of my favorite restaurants in Chicago, if not my absolute favorite. Grab a drink afterward at The Green Door, which is one of the oldest bars in Chicago and still has a not-so-secret speakeasy in the basement (history lesson: a green door indicated a speakeasy back during prohibition). 

A lot of the Michigan Avenue–area restaurants are kind of cheesy and touristy, but The Purple Pig is always a favorite—their wine list is tops and their food menu takes wine-bar staples like burrata and charcuterie to a new level. 

When in Chicago, you absolutely need to have a steak, unless you're a vegetarian, in which case, you might have a fairly difficult time eating in this city. Gibson's has long been my family's favorite steakhouse, but we decided to try Maple & Ash, their younger, hipper offshoot. My filet mignon was cooked to perfection, but more importantly, we sat outside and the people-watching was off the charts. 

Another benefit to being in Chicago in the summer is that you can hit a bunch of its (many) rooftop hotel bars. Z Bar at the Peninsula has excellent cocktails and a prime location right in the middle of things; Devereaux at the Viceroy has a more Miami poolside vibe and feels slightly more mellow. 

For brunch, we hit Third Coast Café, which was one of my high school haunts. It's very neighborhoody and not a scene per se, but the brunch options are solid and it was incredibly comforting to see an institution thriving. 

Where to stay

I have spent many nights at the Drake's Hotel's bar, the Coq d'Or, but had never stayed in the hotel itself. When I was a kid (which I know was a long time ago), the Drake was the grandest, fanciest hotel in the city; the lobby is still gorgeous (those flower arrangements!) and it has benches in the elevators, just like the hotel in Pretty Woman! The rooms are large but feel dated and could use a little updating, however. This was our first time staying in a hotel during the pandemic, and we felt totally safe and that the room was properly sanitized. The hotel restaurant had very limited hours and as I mentioned, the bar was closed, both of which were bummers, but hopefully they'll reopen more widely soon. In terms of location, though, The Drake can't be beat.