Updates from the Windy City and Illinois

A couple weeks ago, Jim and I went up to Chicago for a long weekend. A lot of people don’t realize this, but Chicago is one of the best places you can visit during the summer.

Why? Basically, it’s a respite from the extreme heat and humidity of other places in the lower Midwest. Yes, Chicago gets hot and humid, but it’s nothing compared to how it gets in St. Louis, when you go outside and feel like you’re swimming in a pool by breathing.

Also, Chicago has a lake. Whenever it gets hot, people flock to its beaches, which generally are less crowded or overrun than beaches you would find in other parts of the country. And the water is a nice temperature, so you don’t feel like you’re going to freeze when getting in.

We had a great few days in the Windy City. I went to grad school and then interned in Chicago eight years ago, so whenever I go back, I try to throw in a mix of favorite destinations and also new places that I’ve wanted to visit. This trip was the perfect balance of old and new. Here are some of my favorite places from our trip. I’ll also give a couple recommendations from Bloomington, IL, because we stopped there on the way up, and one from Southern Illinois, where we stopped on the way home.

Bloomington, Illinois

You can easily do the drive from St. Louis to Chicago in a day, but if you want a leisurely route with some small-town charm, I’d recommend stopping for the night in Bloomington, Illinois. We decided to drive up Thursday night and stay at the Vrooman Mansion, a historic house that’s been converted into a B&B. It was definitely worth the stop. The inside is so charming; it really feels like you’ve stepped back 100 years. Also, the breakfast is incredible. We had local grilled peaches with homemade granola, frittata, and turtle pancakes. Everything was so delicious. It was honestly better than some of the restaurant meals I’ve had recently.

Also, while you’re in Bloomington, don’t miss Gene’s Dairy Delight. We stopped there after dinner and the soft serve was incredible. I got a twist with rainbow sprinkles and Jim got a chocolate malt.

Art Institute of Chicago

Every trip I take to Chicago involves a stop at The Art Institute of Chicago. We went there first after we drove up on Friday. I loved this Bisa Butler exhibit with textiles capturing historical narratives of Black life (pictured above). I also took Jim to see the Chagall windows, one of my all-time favorite parts of the museum.


If I could recommend one new Chicago restaurant for you to try, it would be Daisies. We had a great experience from start to finish. They make all their own pasta, and everything is fresh, seasonal, and delicious. I started with the chips and onion dip, which took me back to my childhood eating onion dip with potatoes chips, except these were way better. Then I got spaghetti with fresh tomatoes, and finished the meal with their famous gluten-free chocolate chip cookies. The cookie was exactly how it should be: crispy around the edges, warm and gooey in the middle. I’m tearing up a little thinking about it.

Lost Larson

I’ve wanted to visit Lost Larson for *years*, but I never made it because Chicago is huge and Lost Larson is in Andersonville, north of downtown and difficult to get to on public transportation. This time I had a car, so the morning we went to the beach, I made Jim stop at Lost Larson so we could get breakfast. I got the Swedish cardamom roll and an iced coffee. We ate them in the park near the lake. A woman walked by and said we looked French. Oui, madame.

Montrose Beach

Montrose Beach is one of my favorite beaches in Chicago. It’s big enough so you don’t feel like you have to sit right next to someone you don’t know, it’s beautiful, AND it’s a great middle ground between northern Chicago and downtown. Weirdly, online it says it opens at 11 AM, so I panicked a little because we got there at 10. But luckily it was open and already hopping. On the walk in, a random guy yelled out to me, “It opens at 11,” which stunned me for a second then irritated me. I’m reading a book about the patriarchy right now and I definitely have some thoughts about random men shouting out unnecessary/irritating/patronizing things at women. Don’t get me started.

While you’re at Montrose Beach, you should walk along Lakefront Trail and visit Montrose Pier. I had actually never done this before, but it was a great walk and had a beautiful view of downtown Chicago at the end.

Black Dog Gelato

After the beach, we drove over to Ukrainian Village to get gelato at Black Dog Gelato, one of my favorite places in Chicago. It’s owned by the daughter of one of my professors from grad school, so I found out about it shortly after I moved to the city. I used to go all the time when I lived in Chicago, but lately I only go back in the winter, so I haven’t been in years. I loved revisiting it and cooling down with some gelato after the beach.


Everyone gets excited about Lake Michigan in Chicago, but one of the real attractions in my opinion is the Chicago River. It’s easy to ignore once you’ve lived there a while and it becomes a backdrop during your commute, but if you’re a visitor, you will be impressed by the views. I like to walk along the river near the River North neighborhood at night (see above). The city looks so beautiful lit up at night. You can watch boats go by and people partying on yachts and neighboring patios.

If you want somewhere a little quieter, head to Streeterville near Navy Pier during the day. There’s a River Esplanade park that is peaceful with nice shaded benches and great views of the river.

Lake Taxi

If you visit Navy Pier and want to get to the museums and attractions at the south end of the city, I’d highly recommend taking a water taxi. It’s way better than calling Uber or taking public transportation. We got tickets through Shoreline Sightseeing Chicago and rode all the way across Lake Michigan from Navy Pier to the Shedd Aquarium. They let you bring drinks on board, so I got a frozen margarita and drank it while we sat on the top level and watched the city go by. It was one of the highlights of our trip.

Kim and Carlo’s Chicago Style Hot Dogs

If you visit Chicago, it’s pretty much obligatory that you get a hot dog at some point. Don’t even *think* about putting ketchup on it. You will be exiled from the city immediately. A Chicago-style hot dog has pickles, mustard, onions, tomato, peppers, relish, and is served on a poppyseed bun. I had the best one of my life during this trip at Kim and Carlo’s Chicago Style Hot Dogs stand near the Shedd Aquarium. I wish I could go back and get another one right now.

Buckingham Fountain

Right when I thought I’d seen every tourist attraction in Chicago, I was proven wrong. I saw Buckingham Fountain during our water taxi ride. Located in the South Loop, it’s close to Lakefront Trail and all the museums. Sadly, I did not see Queen Elizabeth, but I get to bask in the beauty of the fountain, and I found a great popsicle vendor.

Mini Mott

I heard about Mini Mott through a St. Louis food writer who visits Chicago more often than I do. He posted some pics that made me want to visit. Their burgers are incredible. You can get a garlic butter burger (pictured left) or their classic that comes with sweet potato straws, pickles, miso butter, and spicy aioli. Don’t forget to get soft serve at the end. They rotate flavors seasonally. I got Belgian chocolate and peach swirl.


Our last morning in Chicago, Jim and I walked over to River North for breakfast at Beatrix. It’s located on one of my favorite streets in the city with a bunch of good restaurants and coffeeshops. I got these lemon ricotta pancakes with lemon syrup and they were incredible; light, fluffy, slightly sweet, and not too filling. They also had good fresh juice (not pictured).

Marcoot Jersey Creamery

At this point you’re probably thinking, your trip to Chicago was basically eating ice cream and hot dogs and not much else. You’re not wrong, but when you’re in a food city and driving through some of the best farmland in the country, what else can you expect? On the way home, we stopped somewhere I’ve wanted to visit for a while, Marcoot Jersey Creamery. Marcoot is well known in the St. Louis area for its fresh, artisan cheese and ice cream. We picked up a bunch of cheese to take home with us, and we finally got to try their homemade ice cream. I’m not exaggerating when I say it’s the best ice cream I’ve ever had. I got the chocolate with Oreos and vanilla with cookie dough.

About Emily Wasserman

Bonjour! My name is Emily and I'm a writer based in St. Louis. I'm also a home baker with a small business, Amélie Bakery. I'm a self-proclaimed francophile and love French pastries and baking.
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2 Responses to Updates from the Windy City and Illinois

  1. Lynn W. says:

    Wonderful descriptions and photos! I feel like I just visited C’go.

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