Chicago is a great U.S. city to visit. I highly recommend it if you haven’t been before, and even if you have, there are likely quite a few things you can do even on a second or third trip. I had been previously, but I planned a trip for my mom.
Crafting the perfect trip to Chicago
Start with the people going on the trip – for ours, it was two adults with a heavy walking focus. My mom loves to explore cities, so I figured Chicago would be an excellent place for her to explore and walk around. We had a long weekend, so there were a few things we couldn’t quite fit in. But, I focused on some of these:
Architectural boat tour
I’d done this before; it was one of my favorite tours in any city. A few companies offer them, and they run pretty regularly except for in winter.
Book your own Chicago architectural boat tour here.
Chicago-style pizza: Giordano’s
For the first-time Chicago visitor, we had to get some Chicago-style pizza. We picked Giordano’s, which was delicious. Just be prepared—it’s a heavy meal, and because it’s so thick and hearty, it takes a while for them to make it. So, it’s not a speedy, quick dinner.
Other Chicago food to try
We didn’t get some of these others in on this trip, but a former Chicago resident also turned me on to some of these, that I highly recommend trying if you have time:
- Portillo’s – for Italian beef sandwiches and Chicago dogs
- Greek Islands – for Greek food with a fun ambiance; there are lots of other restaurants with great reviews in Greektown, too
- Gussie’s Handmade Italian – for tasty Italian food and a yummy cheesy bread appetizer that’s TikTok famous (also near Second City, so it makes for a fun pre-show dinner)
- Rooftop dining – Chicago has some great rooftops. I love grabbing a drink or appetizers at a fun rooftop restaurant or bar
Walking tour in Chicago
Honestly, I love tours—they are often a great way to see many interesting spots in a short amount of time. I found a stellar walking tour: Walking with Colin. Colin was a fantastic tour guide and made it fun, showing us many great spots we wouldn’t have found otherwise. He was hilarious, too.
You can book your Walking with Colin – Chicago Walking Tour here.
Pro tip: Viator offers many options for finding a great Chicago tour (or in cities worldwide). You can read reviews, confirm where you’ll go, the activity level, and other details like where it starts and ends. Check for tours with more than 4-stars and read the reviews to get a feel for them.
Need help booking your own custom-curated itinerary to match the travelers and preferences on your trip? Get in touch – Travel with Ellen can help!
Entertainment in Chicago
There is no shortage of restaurants, bars, shows, and more. We checked out an improv show at Second City. It was so much fun, and they have a variety of options. We also walked down to Navy Pier and stopped by a speakeasy – Untitled Supper Club– with a cool vibe and some tasty cocktails.
Where to stay in Chicago
There is also no shortage of great places to stay. I had some Marriott Bonvoy points available to use, so I found a pretty good deal to book a stay on points at the Fairfield Inn—Magnificent Mile. It’s a great central location—easy to walk, train, or grab an Uber/Lyft to many things. They offered a complimentary breakfast, which had some good stuff and wasn’t too chaotic/crowded. It’s a nice hotel with 4.3-star reviews as of the publishing date in July 2024.
Relaxing in Chicago
There are plenty of spas at the many hotels or stand-alone places to get massages, facials, and more. We found a deal to get a couples massage (since there were two of us). I highly recommend something fun and relaxing while you’re adventuring, too.
The bottom line on Chicago
It’s a great U.S. city to visit for all ages. This itinerary was tailored to adults only, but you can easily make it a kid-friendly trip with the many museums and things to do.
