Chicago, Illinois: 13 Can’t-Miss Places to Help You Explore

I grew up in Southern Illinois, but driving the five hours north to Chicago was a rare treat—so rare, in fact, that it only happened once. I can remember it very well: eating deep-dish pizza, feeling the hubbub of the city, and feeling happy and content in the big city.

Naturally, when Nevaeh said she wanted to go to Chicago for her birthday, I didn’t hesitate. The Windy City has so much to offer its guests.

Before You Visit, You Should Know

It seems like the age-old saying that “April-May and September-October” are the best times to visit; however, I have only visited during the summer and don’t find it too daunting this time of year. It’s warm but not unbearably hot. Everything’s in full bloom, and there is plenty to do.

I’m a jeans or shorts and T-shirt kind of girl, and even in the summer this sufficed. So, wherever your favorite clothing is or what is appropriate for why you’re going, you will need a nice coat, a hat, and gloves during the winter. Surprisingly, you may be going on leisurely travel or have some extra wiggle time during your business travel. In that case, I recommend bringing a swimsuit during summer, as Chicago is on the “third ocean.”

Here’s the local forecast to keep up with what you should wear.

Your Home Away From Home

Hotel

• Embassy Suites Downtown Magnificient Mile If you want a hotel room that will give you space, a wonderful made-to-order “free” breakfast, afternoon snacks and drinks, and a pool for the kids, check out the Embassy Suites. I think they need a referral program because Hiltons are always my go-to, and it’s for reasons like this. You know what you’re going to get.
  • Pro-Tip: I splurged and paid a little extra to get a corner room higher up in the hotel. The view was truly magnificent. One of the nights we were in town, Breanna and I stayed in the room most of the night. Being able to type away on the computer with a view like I had inspired me!

Dig In! Let’s Eat

Breakfast and Coffee

• Dark Matters: Dark Matters has to be the funkiest little coffee shop in Chicago. They focus on specialty roasted beans from El Salvador, Guatemala, Colombia, and Mexico and work directly with the farmers, roasting them in nearby Humboldt Park. We visited their Meddle location, which is painted bright colors and has neon signs on the wall. Even the espresso machine is purple, and even the coffee cups are fun to look at.
  • Recommendation: I will always, always, ALWAYS go for a Mayan Mocha or something similar. Their coffee has Vietnamese cinnamon, Mexican dry cayenne, agave nectar, and African Tikal chocolate sauce.

Main Meals

• Bar Taco: Bar Taco will carry you away, making you feel like you’re on an island. From the blue on the walls to the clear overhead ceiling and the ropes around, you have a good idea of what they serve. Bre and I ordered mushroom and glazed pork belly rice bowls. They were fresh and delicious. It’s a perfect meal if you want something light and filling. After visiting Massachusetts, I couldn’t help but order the warm buttered lobster taco. I was surprised that it came with bits of hominy in it. It’s not traditional but brings back sweet childhood memories, making it much more comforting.
• McDonald’s: Oh yes, I just went there. The McDs I recommend differ from those you would go to at home or anywhere else. This one is at their corporate headquarters and serves international food alongside their traditional menu. I shared with everyone, letting the girls decide. They opted for a Grand McExtreme Intense Cheddar, a Samaurai McSpicy, and McShaker Fries. Nevaeh enjoyed her McSpicy, and my non-burger-loving Breanna said her burger was “actually pretty good.” The fries were the biggest hit since they ordered a second batch before we left.
• Lou Malnati’s: This is the place to go if you want deep-dish pizza in Chicago. And who wants something other than deep-dish pizza in Chicago? We went to the one on the Navy Pier and enjoyed the evening’s cool weather. They were busy (since they are so good), but our server was great.

Things to Do

• Starbucks Reserve Roastery: This is my second one this year! My mom and I visited the one in New York City in April. The girls and I enjoyed walking around and looking at all the things. We did not enjoy the food ordering experience, though (which is the opposite of the NYC experience). We ordered around 11 AM and found they were out of many things, including nitro cold brew to make Nevaeh’s drink brioche bread and the meats to make the sandwiches I wanted. The biggest takeaway from that experience is to go early: they’ll have what you want. The roastery has four stories, making it the largest in the world.
• The Bean (aka Cloud Gate): One of the most significant permanent structures in the United States, Cloud Gate is designed to show off everything Millennium Park encapsulates: from the greenery to the downtown skyline, it captures it all. Initially unveiled in 2004, they have revamped in the last few years, including adding an AI tool to help you navigate your Chicago experience. While you’re there, spend a little more time enjoying Millennium Park. There’s the Lurie Garden, where you can walk through a maze of flowers or enjoy the music at the Jay Pritzker Pavilion.
• “Goth Target”: Inside, it’s like many other Targets, albeit it is two stories, but outside, it’s a different story. Nevaeh knew about this one and asked if we could find it. Amazingly, it’s within walking distance of Millennium Park, so off we went. This TikTok famous building was once the headquarters of the department store Carson Pirie Scott and has been a registered Historical Landmark building since 1975. If you go, check out the second-floor rotunda with informational placards that Target installed near the windows.
• Navy Pier: Built in 1916, the Navy Pier is the second most visited attraction in Chicago. The area is lively and vibrant, with plenty of stuff to do, even on a budget. There’s Polk Bros Park, where the water fountain mimics different nature elements, or the lawn, where various events happen year-round. We were there during the summer and were lucky enough to see the fireworks show that the city held every Wednesday and Sunday night. We also ate at Lou Malnati’s while we were here. Initially, we planned to go to the tilt but decided to go on the Ferris wheel instead. It was a great experience to see the sunset over the pier to one side and downtown on the other.

• Garfield Park Conservatory: This plant conservatory has over twelve acres of gardens. Two acres of which are indoors, and ten are outside. It’s free to visit, but plan and get your reservations online. We did a walk-up but came when they were not super busy- early on a Friday morning during mid-summer. Before you go in, be sure to look outside of the building. It was designed to look similar to the silos of the midwestern states, the architect paying tribute to the farmer’s contributions. Once you leave the lobby, you will be transformed into a place with lush tropical trees and waterfalls. They even transform the kid’s area with a playground and plants you can touch. You can easily spend hours here, and it did get a bit overwhelming, so plan accordingly.
• The Garden of the Phoenix: If you have less time than the Garfield Park Conservatory, check out the Garden of the Phoenix. This park was designed to show the mutual respect between Japan and America, which has spanned more than 120 years. If you go during the right time of the year, over 170 cherry blossom trees bloom, creating a sea of pink to surround you and give you shade. Sky Landing is my favorite part of the park, even more so than the waterfalls. Sky Landing is a structure with a dozen 12-foot tall lotus flower petals donated by Yoko Ono in 2016. During the dedication, she described the piece as a “place where the sky and earth meet and create a seed to learn about the past and come together to create a future of peace and harmony, with nature and each other.”
• Chinatown: If you want authentic Chinese food and feel like you’re in yet another world, check out Chicago’s Chinatown. We went to a boba shop, walked around briefly, then landed at a cheesecake shop. I opted for a cheesecake pudding, and it was light and airy, so it was very delicious. Bonus? They have a great view of downtown!
• Added Bonus: If you have extra time, drive the thirty minutes southwest to Winnetka, Illinois, and check out the Home Alone house. There are typically many tourists joining in on the fun- everyone is trying to bring out their inner child while they are yelling, “Merry Christmas, ya filthy animal!”

Wrapping It Up

If nothing else, Chicago is a city that can make you feel like you are somewhere else while still dangling that beautiful skyline on a string in your rearview, reminding you that it’s still there to lure you back in. There is still much to explore, and I can’t wait to return!

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