Midwest Adventure 2018, Part 1: Chicago, Illinois

Our family returned last week from a 17-day, 6-state, 1-province, 11-city midwest adventure. The primary reason for the trip was to attend a wedding in Ohio. We knew that we wanted to spend 4 or 5 days in Ohio, then spend another week or so exploring the surrounding states. I played with several different itineraries, each hitting many cities that we were excited to explore. After a lot of research, we decided to fly into Chicago, then get a rental car. We'd visit Michigan on the way to Ohio (crossing the Detroit River to visit Windsor, Ontario), then hit West Virginia, Kentucky, and Indiana, then fly home from Indianapolis.

So how was the trip? Fabulous! I can't wait to tell you about all the great places we visited, the delicious regional foods we tried, the hotels we loved, and the mishap that landed us in the US Detention Center on our way back to Michigan from Canada. Today, it's all about Chicago.

But first, a disclosure: Because I blog about educational travel, I received free admission tickets, discounts, media rates, and other benefits for some of the hotels and attractions we visited throughout this trip. Many of the attractions we toured are free to everyone. I paid full price for the rest. This has no bearing on my reviews. Everything I'm sharing is something that I whole-heartedly recommend. If you notice any gaps in my narrative, it is because I didn't love a particular attraction, restaurant, or hotel enough to recommend it to you, regardless of how much I paid or didn't pay.


We landed at O'Hare at 8:00 PM on Sunday, July 22. After a quick dinner, we followed the well-marked route to the L Train. I haven’t been to Chicago since I was 16, so even though I’d ridden it then, I didn’t remember anything about it.

Our experience was great - the Blue Line train was clean, safe, and convenient, filled with lots of other tourists with luggage. And, at $5 a person, it is a much more affordable option than any other way to travel the 45 minutes to downtown Chicago. We got off the L at the Clark/Lake station and walked two blocks to our hotel, The Wit. It's a Hilton DoubleTree property. 

If you visit downtown Chicago, stay at The Wit. It is in a great location, the room was clean and very comfortable, the staff was super friendly and helpful, and we were greeted with warm cookies. 

We woke up refreshed on July 23, eager to explore the Windy City. Because we only had a single day in Chicago, I wanted to get an overview and see as much as possible in the limited time. We started with the Chicago Trolley and Double Decker Co. Hop on Hop Off tour. The tour has 14 stops, including two that are an easy walking distance from The Wit, which was handy. We could have gotten off at any of the stops, but we chose to do a round-trip. We learned a lot from the narration and enjoyed the beautiful views from the top of the trolley. 

After visiting each of the 14 stops and seeing how many neat attractions Chicago has, it was very tempting to drop the rest of our plans for the day and hop on and off at each of the stops. But we stuck with our plan, got off at Millennium Park, and went in search of Chicago-style hot dogs for lunch. With some help from friendly locals, we found Relish Chicago Hot Dogs.

If you're not familiar with Chicago-style hot dogs, the first thing you need to know is what is NOT on them. 

A proper Chicago-style dog has yellow mustard, a bright green relish, chopped white onions, a dill pickle, tomatoes, pickled peppers, and a dash of celery salt in a poppy seed bun. It's pretty much the exact opposite of what I like best on a hot dog (ketchup, mayo, and shredded cheddar cheese), but hey, when in Rome.   

Our trolley tickets came with coupons for free popcorn at Garrett, so that was our next stop. All the flavors we tried were delicious, but I highly recommend combining Almond Caramel Crisp with Buttery. Yum!

Next on our schedule was the Chicago Urban Adventure Quest. We've loved all the Quests we've done (11 and counting!) and believe there is no better way to get to know a city. The Quest took us all over downtown, including to The Bean... 

... the start of Historic Route 66...

... the awesome and totally unique Crown Fountain...

... the beautiful Riverfront... 

... and my personal favorite, the Chicago Tribune building, which has pieces of famous buildings and materials from all over the world embedded into the exterior of the building, brought back from Tribune correspondents all around the world. There’s everything from a piece of the White House to a chunk of the Great Wall of China to a piece of the pyramid at Giza to petrified wood from California. 

We finished the Quest with one dumb mistake, putting us at #61 on the All-Time Leaderboard. Not our best showing, but we learned a lot and had a great time. And I know that we saw a bunch of cool things that we would otherwise have walked right by. 

Speaking of walking by, we passed many painted lighthouses during our time in Chicago. They're temporary, which is a shame because they are so beautiful. The goal is to shed light (hence the lighthouses) on people with disabilities. About half of the 51 artists are living with a disability. If we'd had more time in Chicago, I would have found and photographed all of them. Fortunately, you can see and learn about the inspiration behind each lighthouse online. Allow a lot of time to look at them all and listen to the artists speak. It's amazing. 


We decided to get an early dinner to avoid the crowds at Lou Malneti’s, home of the best (say many) deep-dish pizza. 

It was a good decision. We arrived at 5:00 PM and ordered right away; by the time our pizza came, the place was packed. 

The pizza was cheesy and gooey, with a great tomato sauce, lean sausage, and delicious buttery crust. I’d eat there again and again. The three of us split one small 'Malnati Chicago Classic.' It wasn't quite enough food for us, but that wasn't a problem because when I'd asked the staff at The Wit to recommend where we should try deep-dish pizza, they gave me a coupon for a free Chocolate Chip Pizza at Malnati's. It was absolutely perfect, and just the right size to fill us up. 

At only $15 plus tip for the three of us, Malnati's was not only delicious, but ridiculously inexpensive. We'd be regulars if we lived in Chicago, no doubt about it. 

Our trolley tickets included a night tour of Chicago to see the beautiful lights, but we were all exhausted and wanted to get to sleep for our early morning. If we'd had an extra day in Chicago or didn't need to race off in the morning, we definitely would have done the night tour. I love that it's included in the price of the trolley tickets. 

We weren't ready to say goodbye to Chicago so soon, but it was time to head east and continue our adventure. But first, I walked two blocks from The Wit to get us donuts from Do-Rite Donuts. I'd heard they were the best in the city. 

Since we only tried these donuts, I have no idea whether or not they're the best in Chicago. But I can say that they were spectacular. They were all delicious, but my personal favorites were the Pistachio-Meyer Lemon, the Michigan Apple Fritter, and the Valrhona Chocolate Cake. And Do-Rite Donuts is the most efficient donut shop I've ever seen. Despite a line in front of me, I was in and out in under 5 minutes.

There's one more thing I want to mention about The Wit. (Can you tell I loved this hotel?) In the hallways, they have recordings of different birds peeping and singing. That was cool, but the neatest thing is that the bird calls change depending on the time of day. In the early morning, there’s a rooster interspersed with other morning singing. In the evenings, owls. Late nights, crickets. It is awesome.

Anyway, after we finished our donuts and packed up, Steve walked two blocks to the car rental pickup. We'd originally thought we'd just rent a car at the airport and park it in Chicago for the two nights, but as soon as I learned that it costs $60+ per night to park downtown, we quickly abandoned that idea. With a car rental place so close to The Wit, it was no problem to pick it up when we actually needed it, rather than unnecessarily paying rental for two extra days AND parking for two days. That was a few hundred dollars saved we could put toward the rest of the vacation. 

We loved everything about Chicago and can't wait to go back someday. Tomorrow I'll tell you all about our next destination: Lansing, Michigan.


  1. Oh wow. What a fabulous family adventure! Chicago sounds amazing!

  2. Hi Cindy! WOW! Chicago looks amazing. I have never actually visited the city - I have been to the airport when we adopted Anne from China, and drove through when I was driving home from CA with my husband when we were first married. It looks like you had a wonderful trip, filled with good food and awesome sights!

  3. How awesome!!! So excited to read about your Chi-town experience!! Loving all the photos and those donuts look YUMMY!!!!!!


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