The moment I read The Devil in the White City I knew I HAD to see Chicago. The Devil in the White City delves deep into the history of the 1893 World’s Fair in Chicago and into stories of notorious serial killer H.H. Holmes. Before reading the novel I really never knew much about Chicago or had much interest in going there (besides my lifelong goal of visiting the Home Alone house). However, as I began to look into more of the history and things to do it instantly became one of the top cities on my bucket list and I’ve added things to my “Chicago specific” bucket list over the years. The third biggest city in the US, the Windy City is packed full of history and culture. My mom and I decided to make a fairly spur of the moment trip to Chicago over a long weekend off of work. We were flying in late Friday night and flying out early Monday afternoon. I went instantly into crunch mode trying to figure out how to cram my whole list into 2 days and as a result of careful planning, I was able to fit almost all of my list in so I’m going to share my ‘48 hours’ in Chicago, what I saw (and what you should see when you visit!), and how I made the most of my 2 days in the windy city!
Where I Stayed:
Hampton Majestic Chicago Theater District
I picked this hotel because of the price. It was very reasonable for the key thing I was looking for which was: location, location, location. As a first time tourist of a new city I wanted somewhere that was pretty close to most of the touristy spots I wanted to visit. It’s walking distance from almost all of them. The Bean, Millennium Park, The Skydeck, and Ogilvie Station are all about ½ mile, and the Navy Pier is a 1½ mile walk. Breakfast is also included which is always a plus. The rooms are spacious and clean. It was the best I could find for the price. Highly recommend if you’re looking for somewhere great and close to everything!
Day 1
Chicago Theater
My first stop was the Chicago Theater to see the ever famous Chicago marquee. Currently owned and operated by Madison Square Garden Inc., the theater is an active venue for comedians, theater, magic shows, concerts, and more. The marquee is a popular photo spot in Chicago and of course I wanted to check it out!
The Bean
You’ve seen it in all your friend’s pictures from Chicago, you’ve seen it in every blog post about Chicago, now go see it in real life. Cloud Gate aka The Bean is a sculpture located in Millennium Park that was crafted around 2005 by Sir Anish Kapoor. “But isn’t it just a statue? That’s stupid” – My Mom Before She Saw It. So much more than just a quirky art piece, the bean has really cool reflective views of the Chicago skyline and other fun reflective illusions that make it a must see. If nothing else it’s free right? So simple but probably one of my favorite things I saw.
Skydeck
Oh, the Skydeck. If there’s a building with a view of a cityscape you can bet I’ll be there. The highlight of the Skydeck is most definitely the ledge…a glass box you stand in to get the coolest photo op over the city. Have your poses ready because you get a max of 60 seconds to snap your best pictures. It wasn’t overly crowded the day we were there so wait times weren’t awful but if you’re going in peak times like summer I might look into the express pass in order to save some time in the lines and maximize your trip time.
Giordano’s – Deep Dish Pizza
Pretty much my only food goal going in: the deep dish pizza. The origin is a bit unclear but it is thought to have originated around 1943. VERY different from the paper thin NY pizza I was used to, Chicago deep dish features a thick crust, tomato sauce filling, and TONS of cheese for a mind blowing cheese pull. I wanted to try the best. As I was doing my research before my first Chicago trip, I was pulled into the great “Giordano’s vs. Lou Malnatis” debate. I ultimately decided to try both while I was there but my top choice was Giordano’s (and it won by a long shot!). When you’re on a time crunch the 40 minutes it takes to bake the pizza may sound daunting but take the time and wait. 100% worth it. And be sure to be ready to video that epic cheese pull!
Devil in the White City Tour (Weird Chicago Tours)
Not necessarily on any typical “must do” list, the top of mine included a Devil in the White City tour through Weird Chicago tours. The tour focuses on the history of H.H. Holmes and the 1893 Chicago World’s Fair but also includes a fair share of other Chicago history. I really liked that I got to go out of the heart of the city and see some parts I wouldn’t ordinarily have gotten to see without a car. If you’re into darker history this is a great way to see a lot of Chicago in a short amount of time while learning a lot in the process.
Navy Pier/Centennial Wheel
We had some time between the tour and our late show so we decided to go ahead and check out the Navy Pier. I’m not sure what exactly I expected from the Navy Pier but it was different than I thought it would be…in a good way. A cute little market, a crystal garden, a children’s play area, and an outdoor area – the Navy Pier has a little something for everyone.
One of the most well known tourist attractions in Chicago, the Centennial Wheel is a giant closed in Ferris wheel that has been featured in many feature films. Of course we had to ride it. The time of year made lines super short so we didn’t have much of a wait – though I imagine lines get MUCH longer in the summer. We also ended up with a whole pod to ourselves. The views are fantastic and I certainly think it’s just something you have to do in Chicago.
Garrett’s Popcorn
Garrett’s has stores everywhere in Chicago but we caught the one at Navy Pier (time saving, for the win!). I’ve long been a fan of the cheddar/caramel flavor combination but I’ve heard that Garrett’s is the best of that…and how true that is. I can’t say enough how much I recommend their Garrett’s mix. The cheddar melts in your mouth and the caramel is the perfect texture - crunchy without being sticky. We got some to munch on right away and some to take back for later. It makes great gifts to take home and if you can’t get enough you can always order it to get it shipped to your house.
Bombobar
We went to Chicago in the fall…it was pretty chilly. After walking around all day what’s better than a hot chocolate? Better yet, what about a hot chocolate that makes a great Instagram picture? I’m ALL about instagrammable food/drinks and Bombobar is certainly Instagram worthy. Besides just a cute picture, the hot chocolate is super yummy. Perfect way to warm up on a chilly day.
Second City Show
What do Tina Fey, Steve Carell, Jason Sudeikis, and Mike Meyers have in common? They all got their starts with the Second City. The Second City opened in 1959 as a small theater and has now grown to one of the biggest comedy scenes in the world. From sketch comedy to improv, Second City offers several shows at different theaters around the city every night. We chose the 11pm improv show (past my bedtime but who needs sleep right?). The improv was hilarious and different from your typical cookie cutter improv. The talent is unmatched and who knows, you may be catching the next SNL cast member…
Day 2
Home Alone House
Home Alone is one of my favorite movies of all time. The second the clock strikes November 1 I’m pulling out the DVD and the sweater and ordering “a lovely cheese pizza just for me” for a movie night. I certainly don’t need it to be Christmas time to watch it but around the holidays Home Alone is a ritual at my house. Since it was early November (and one of my original reasons for wanting to visit Chicago) I decided to use my day 2 to make the trek out of the city to Winnetka to see the house. I took all my props and had a mini photo shoot. It was fantastic. This side trip did take most of the morning…if you’re doing Chicago on a time crunch (without your own car) and aren’t a HUGE fan, it’s probably not going to be worth your trip. However, the time it took was 100% worth it for me.
Lincoln Park Zoo
Since I had checked off most of my bucket list by this point we decided to drop by the zoo. Normally I might skip this since most zoos are the same but the history of this zoo was pretty intriguing to me. Founded in 1868, Lincoln Park Zoo is one of the oldest zoos in North America. It is also one of the only zoos in the US that has free admission. The zoo is pretty big. A lot of the animals were put away for the season so it’s hard for me to judge it when it wasn’t really at its peak but it was still a really nice walk. Oh and definitely stop and do the $2 photo booth pictures...so cheesy but it's a cheap and funny souvenir (you get a print there and they email you all 3 afterwords!).
Portillo’s
If we’re being honest, I didn’t even know Chicago had its own style of hot dog. Now I’m obsessed. The classic Chicago dog: a poppy seed bun, yellow mustard, relish, chopped onion, tomato slices, dill pickle spear, sport peppers, and celery salt. Want the best one? Portillo’s is the place to go. Portillo’s has a sports bar feel and also serves up other classics like Italian beef sandwiches. It was started in 1963 by a couple of brothers who used their whole life savings to open a hot dog stand. The prices are moderate and well worth it. Grab a hot dog (and one of their cake shakes!) and prepare to have a whole new view of hot dogs forever.
Day 3: The Final Hours
Do-Rite Donuts
In my research I heard that trying a Chicago donut was a thing. I’m not a huge donut person but I read that Do-Rites had some of the best. I found out there’s one in the lobby of the Willis Tower (same building where the Skydeck is) which was close to the hotel. The donuts were massive (and they had Nutella iced coffee, what?) and were overall pretty good. They were a little pricey though. If you’re a donut freak by all means go for it but if you’re running short on time you can probably safely skip this one.
Uncommon James
With just a couple of hours left (and with the goal of fitting as many things as I possibly could into the time) I had one more place to visit. Uncommon James in a boutique store opened by Kristin Cavallari. Though a bit pricey it has a variety of jewelry, clothes, and home goods. I browsed a while and spent WAY too much money and took some pictures in their Instagram hot spots. Great way to end a whirlwind 48 hours.
Overall I was able to fit a TON of activities into a short amount of time. My bucket list might be different than your bucket list and the timing may be different but I hope you either find something new from my experience or are inspired to maximize a short amount of time if that’s all you have. Keep in mind – I visited Chicago in early November. While I still feel like I got a full and amazing experience, some attractions were closed or not at their peak. We also avoided some other highly recommended activities such as an Architecture Cruise due to cooler weather. That being said, there were several plusses to visiting around this time of year such as significantly shorter lines at busier tourist attractions such as Skydeck and Centennial Wheel. Chicago is a beautiful city with so much to see and I still can’t believe I fit so much of my bucket list into a mere weekend. (If anyone has any suggestions for anything else I should see please leave them in the comments!!). I can’t wait to go back and see what else Chicago has to offer.
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