Chicago Weekend

Chicago boat tour

Last weekend my brother and I spent the weekend in Chicago.  We’ve talked about doing something together (just the two of us) for years, but with four little kids between us, finding a time we can both pull ourselves away has always been a challenge.  Last weekend, we finally made it happen, and it was such fun!

We decided to meet in Chicago, as it was (somewhat) centrally located between where he lives on the East Coast and where I live on the West Coast.  Plus, it’s a city we both really like but haven’t spent a ton of time in.

Our 48 hours (or so) there were completely awesome and memorable.  We did so much in a short span of time, but I totally left wanting more!  I really can’t wait to return and continue exploring this amazing city!  (I’m just going to wait until winter is over, because my California-thinned blood probably can’t handle the cold there anymore!!)

What We Did

  • Architecture Boat Tour– This was so awesome!  I am so glad we were able to go on this boat tour of Chicago’s architecture, as it was 1) totally beautiful, 2) quite informative about Chicago’s history and architecture, and 3) a lovely way to spend an afternoon (on a boat, coasting through the middle of Chicago and all its amazing buildings, with a cup of hot chocolate in hand– it was a bit chilly and windy, after all).  This was easily the best thing we did while we were there.
  • Stayed at The Peninsula Hotel – This is a wonderful hotel, and we stayed on one of their recently renovated floors.  The living room of our suite (which I am still kicking myself for not taking a picture of) looked like it belonged in a futuristic Tom Cruise movie.  Its gorgeous dark wood built-in desk with a beautiful striped marble back was stocked with everything you could ever need in an office-related pinch, and the ginormous tv over it looked like it was capable of directing world affairs in the aforementioned Tom Cruise movie.  And I had a lobster roll in the hotel lobby restaurant that brought me back to my New England roots (but with a twist).  I Instagrammed it, and the photo still makes me salivate when I look back at it.
  • Mindy’s Hot Chocolate– This is a great restaurant for brunch (with over-the-top delicious hot chocolate).  It is located about 15 minutes from downtown in a really cool area called Bucktown (my brother kept remarking that it felt like the Brooklyn of Chicago).  It is focused on delicious farm-to-table food, and our breakfast here was ridiculously good.  I’m talking eggs like you read about (mine were infused with mushrooms, cheese, and herbs), perfectly cooked bacon, and the most scrumptious thick-cut Challah toast.  Not to mention the hot chocolate for which the entire restaurant is named, which is completely decadent and wonderful.  And it comes with two big marshmallows that will make you feel like a kid again).

Mindy's Hot Chocolate

  • Graham Elliot Bistro– We ate here our first night, and all I can say is– WOW.  The restaurant holds two Michelin stars (by the way, have you read the article in Vanity Fair about the stress Michelin stars cause their chefs?  It’s a fascinating read.) and apparently Graham is a Master Chef judge.  The food is divine.  We ordered the parmesan truffle popcorn and frites with bacon major as appetizers, and I nearly died from the deliciousness of it all.  I actually forget what I ordered after that, because I’d already gone to food heaven.

Graham Eliot Bistro

  • Lou Malnati’s Pizza– This pizzeria is exactly what you’d want from Chicago pizza.  They have a scrumptious deep dish pizza, and we spent an evening here watching the Cubs play in the playoffs.  I’d definitely go back.  I also need to go back to Giordano’s Pizza, because right after we got off the plane we were starving and ate there, but made the mistake of ordering the thin crust pizza.  We did this because we had a “real” dinner scheduled in a few hours and didn’t want to spoil it, but watching all the mouth-watering deep dish pizza go by nearly killed me.

Giordano's Pizza

  • Glazed and Infused Donuts– I have been hankering for a fancy donut for a while (since they took over my Instagram feed sometime this summer).  This place was so great (with beautiful and delicious donuts which my brother and I both carried home on our respective planes home to bring back to our families, and they also have some wild flavor options (like the Maple Bacon Long John, which looks like an eclair with a huge strip of bacon on top!).

Glazed and Infused Donuts

  • Yolk– This is a great breakfast place (and a chain, so you can find a bunch of them).  We ate here before we went to Hot Chocolate (which is on another level) and thoroughly enjoyed it.
  • Shopping on the Miracle Mile- We walked around the stores here and went into a handful (largely looking for treats to bring back home to our kids).  The Dylan’s Candy Bar store gave a nearly-overwhelming array of candy to choose from, and we left stocked for our kids!

Dylan's Candy Bar Chicago

What I Want to Do Next Time

  • See a show at Second City– I thought about this too late, and tickets were already sold out. I would love to see a improv comedy show at the place that spawned Tina Fey, Stephen Colbert, Chris Farley, and Steve Carell, and Amy Sedaris (among many other great comedians).
  • Millenium Park– A bunch of people told me this was a great place to go, and it’s also where the famous “Bean” is (that big silver bean-shaped sculpture).
  • Art Institute– This has been voted the #1 museum in Chicago and is supposed to be an amazing way to spend a day.
  • Eat at Pelago–  I confess, we actually had reservations at this fine Italian restaurant, and I’d already checked out their menu and tried to narrow down to a few options their amazing offerings (I am a sucker for homemade pastas.).  But after our second day in Chicago, during which we walked nearly all day, we canceled our reservations in lieu of pizza and the baseball game.  I definitely want to go there next time.
  • Eat at Bistronomic– This small plates French bistro comes with high recommendations.  I really want to eat there next time as well.
  • Have drinks on the roof deck of the Trump Hotel– I’ve heard this is the best place to have drinks in the city.  It’s supposed to have a stunning view.
  • Have drinks at Aviary– I’ve heard having drinks here is truly an experience, where cocktails are state-of-the-art and like nothing you’ve ever seen before.

I loved my time in Chicago so much, I wanted to pass this itinerary along, in case you’re going sometime soon.  Do you have any places you know and love in Chicago?  Maybe next time I’ll even stay for longer!

O'Hare airport


  • Katherine Simon

    Did you go to ikram and Blake? My 2 favorite independent stores on the planet!!

    • I went to Ikram last time I was in Chicago and LOVED it!! I definitely need to go back next time. And I’ve never heard of Blake. Can’t wait to check it out!


  • Danny Goldfarb

    Thank you for all this info, Ali! My friend is going in January and Steve and I are going in June (unless our son and his wife’s baby comes early).

    • Linda-
      You are so welcome!! What a wonderful place Chicago is. I can’t wait to hear all about your trip!