What I’ve Learned from Six Trips to Chicago


Since I moved to the Midwest in 2012, I’ve been fortunate to enjoy six trips to Chicago, each time with different loved ones. I’ve been to many of the tourist attractions more than once, and have found some off-the-beaten-path gems along the way. Read on to find out what I’ve learned!

Lincoln Park Zoo

The Lincoln Park Zoo is one of my favorite places in Chicago. It’s free, has a wide variety of animals, and as you might guess from the name, is located within the beautiful Lincoln Park. A couple highlights include the lion house and the primate house. Go when a zookeeper is giving a talk in the primate house and you might get to see some monkeys making tools out of bamboo to reach a peanut butter treat. While in the area, I recommend taking about an hour to see the Lincoln Park Conservatory, the Alfred Caldwell Lily Pool, and some great views of the Chicago skyline. Do all of these activities and take a walk along Lake Michigan, and you have yourself an entire day of free Chicago activities. On my next trip to the Lincoln Park area, I’m planning on stopping by the funky and odd Oz Park, which is apparently a tribute to the writer of The Wizard of Oz and contains statues of its characters.


Overlooking the Chicago Skyline

The most popular way of seeing the skyline from above is the Skydeck Chicago. This is on the 103rd floor of Willis Tower, which most locals still refer to as Sears. Though this is a busy tourist attraction, it’s undeniably exhilarating to stand on the glass floors and look directly down at the buildings below. It has got to be one of the most heavily instagrammed spots in the city, though you may have to wait in another small line to get good photos. Basic admission is $23, or you can pay $49 for an express pass. At that rate, you may as well look into getting a Chicago City Pass for $99, which includes an express pass and admission to four other tourist attractions. Whether or not an express pass is worth it depends on the day and timing of your visit. I’ll admit that I’ve been to the Skydeck three times when friends are visiting from other parts of the country; twice I’ve waited for hours to get in and the third visit went quickly. If you’re going on a weekend during peak tourist season, be prepared to wait.





A solid, more relaxing alternative to the Skydeck is the Signature Lounge, located on the 96th floor of the Hancock building. Though drinks range from $9-16, this is cheaper than a visit to Willis/Sears Tower, and you get to sip a drink while looking at the skyline. There will likely be a wait (both times I’ve been it has taken about 30 minutes), mostly because it takes awhile to get folks through the elevators. Once you’re up in the lounge, you can tell the host whether you’d like the first table available or if you’d wait longer for a window seat. This most recent time I went with my friend Jackie, we lucked out and got this amazing table:


Of course, you can also think about when you’d most like to see the skyline: during the day? At night? At sunset? Just plan accordingly.

If you don’t get the table you’d hoped for and you identify as a woman, check out the women’s restroom for the ultimate view.

Architecture Tour

I’ve asked Chicagoans what their #1 recommendation is, and often it’s an architecture tour. I went on a 90 minute tour with Wendella Boats for $35.50, and I concur that this is one of the best attractions you can partake in. You can either make reservations ahead of time or just head to the Chicago Riverwalk (near the intersection of Michigan & North Walker) and ask for the next available tour. There are a handful of companies that offer these and $35 seems to be the going rate.


The Emporium Arcade Bar

Buy a drink and some tokens and you’re all set for an evening of vintage arcade games. I played ExciteBike, Arkenoid, Paperboy, and other classics. My inner nerd absolutely loves this place. One caveat: always have a trusted friend keep an eye on your drink while you’re enthralled in a game. I haven’t heard about any issues around this at the Emporium, though I think this is best practice in a bar with lots of distractions. I’ve only been to the Wicker Park location, though there’s also one in Logan Square.

Veg-Friendly Haunts

Three words: The Chicago Diner. There’s usually a wait, but it’s well worth it for their varied vegetarian and vegan menu, including the best vegan milkshakes I’ve had to date. There are two locations; I love the one on Halsted because it’s in an LGBTQ+ friendly neighborhood, complete with placards commemorating gay rights activists.


On most of my visits to Chicago, I also make sure to hit Native Foods. I fell in love with this vegan chain in the Portland area; it’s a place that my whole family can go (veg and carnivore alike) and be completely satisfied with their meals. The original location is in Wicker Park, and a second is on Clark Street downtown. As I’m writing this I could really go for a Kale Macro Bowl and some of their sweet potato fries with a secret spice combination (one is cinnamon). They also have an array of burgers, sandwiches, and other vegan takes on standard diner fare.

For raw food lovers, Karyn’s is great too. My favorite is their raw cheesecake.

Lastly, Big Bowl is a chain that’s a guilty pleasure for me. They offer both Thai and Chinese dishes. I’ve been to locations in downtown Chicago and Chicagoland suburb Schaumburg. If you’re not sure whether or not a meal meets your dietary restrictions, just ask. I’ve found the servers to be pretty knowledgeable about the menu and willing to check ingredients if needed.

Millennium Park

As touristy as it is, it’s fun to visit the bean (or technically, Cloud Gate) and Crown Fountain, which features locals’ faces that spew water every five minutes. Go early in the morning if you want to get fewer tourists in your photos. Head south to meander through the beautiful Grant Park.



The Shedd Aquarium

A number of attractions are just south of Grant Park: the Art Institute, the Field Museum, the Adler Planetarium, and the Shedd Aquarium. Having been to a number of large aquariums, the Shedd is one of my favorites. You can spent much of a day there, but you do have to pay a whopping $30.95 for adult admission. If you’re visiting more than two main attractions, it may make sense to purchase a Chicago City Pass in advance for about $99.

The Mag Mile

The Magnificent Mile is known as one of the premier shopping destinations in the U.S. Big spenders can find luxury boutiques like Burberry and Chanel, or if you’re thrifty like me you can head straight for the sale section of H&M. There’s also no shortage of Chicago souvenirs available, from Garrett’s popcorn to Blackhawks gear.

Saved by the Max

For a limited time, head to this pop-up restaurant in Wicker Park for a 90’s throwback. I wouldn’t say that this is a replica of Saved by the Bell’s “The Max,” but it is a very good rendition. Your server will be dressed like Max or Kelly Kapowski, you can order a Max Burger, and you can pose like you’re a host of KKTY. What’s not to love? Well, you have to either purchase expensive advanced tickets for specific meals, or just go for drinks late at night. If you go late, plan to wait in line outside. Also, I don’t think anyone is raving about the food; it’s all about the experience.


Taking a Water Taxi

For $5-8, you can get a nice view of Navy Pier from a water taxi. This is my preferred way of taking in Navy Pier- much better than actually being within this kitschy area. Check here for routes and exact prices.


Lynfred Winery

The Lynfred Winery in Roselle is definitely worth venturing out of the city. Though their tastings are a bit pricey at $11, you get seven sizable pours and the wines are impeccable. You can also take each pour outside on nice days. As a bonus, all tips given to winery staff go to a selected charity of the month.


Lake Michigan

Last but certainly not least, Lake Michigan is the crown jewel of any trip to Chicago. I’ve walked along Lake Shore Drive many times, sometimes from downtown all the way to Lincoln Park or Halsted. It provides gorgeous views of the skyline and Navy Pier, and in the summertime is great for spending time on the beach. At moments it might feel like you’re suddenly on MTV’s Spring Break. Does this count as a cultural experience?


What should I make sure to visit next time I’m in Chicago? Leave your comments below!


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