Chicago In a Weekend

When you do a big city in one weekend, you must prioritize – that’s why I’m here, to tell you the must-see attractions in Chicago. We live a little over 5 hours from Chicago and left around 3pm on a Friday and made it to Merrillville, Indiana by dinnertime. As a suburb of Chicago, Merrillville knows good and well why you’re there, but they make the best of it. There are plenty of good restaurants, but why not check a Chicago staple off your list and save yourself some time in the city??


Portillo’s, Portillo’s, oh Portillo’s. Their menu is full of delicious options, but they’re KNOWN for their Italian Beef Sandwich. Do it. You won’t regret it. But the order is a bit complicated, so stay with me. You can get the sandwich with or without peppers – sweet peppers or hot giardiniera peppers (I get it without). Next, how much gravy do you want? You can go with dry, splash or dipped. If you don’t specify, you’ll get a splash of gravy (which is what I do). Last, and most important, ADD CHEESE (I add mozzarella). Pick one of their amazing sides (CHEESE FRIES) and chow down. And if you can’t catch this staple outside the city, you’ll have plenty of opportunities in Chicago.


Chicago Parking

On to Chicago! Merrillville, Indiana is about an hour outside the city. Don’t pay the outrageous hotel prices for parking! You’ll find great parking a block or so from your hotel. We used Spot Hero to find a great garage just a block from our Magnificent Mile hotel and saved $25 (plus tip, since we didn’t have to valet). Check the internet for discount codes! We saved an additional $5 making our 28-hour parking job cost $45 instead of $70+ at the hotel.

Chicago Hotels

Let’s talk hotel. I’d recommend staying on/near the Magnificent Mile (AKA Michigan Avenue). This will keep you within walking distance of the main attractions. We stayed at the InterContinental, which is home to the Michael Jordan Bar & Steakhouse (which we did not eat/drink at, but have heard great things about). We were upgraded to a tower with a good view and lots of space. It also has a really cool pool, so don’t leave without taking a dip (or at least stopping by).


Magnificent Mile (Michigan Avenue)

We rolled into the city around 9:30am, checked-in to the hotel and then set out to explore Michigan Avenue. Michigan Avenue is the main commercial street in Chicago, but don’t waste your time shopping (we all know you only do that online now) and head to the nearest bridge to get that quintessential Chicago river photo (pictured below is the view from the DuSable Bridge). Near the bridge was a giant Abraham Lincoln statue and an unknown man (my husband said Mr. Rogers, I said Ronald Reagan). After a quick Google search, we discovered it was, “the common man.” Well, “the common man” needs a wardrobe update, because that sweater, those corduroy pants and mall-walker sneakers aren’t doing it for me. I digress, the statue is portraying President Lincoln explaining the Gettysburg Address to a man stuck in the 1970’s. Let’s move on…


It’s now lunchtime! Just before 11am, head over to one of Chicago’s famous deep-dish pizza joints and find out what true love is. Make sure to read my post about two of Chicago’s most well-known pizza places.

Architectural Boat Tour

Now that your belly is full and your carb-coma is kicking-in, head down to the new riverwalk and find an architectural boat tour. Nerdy? Yes. Lots of fun? Absolutely. You’ll have plenty of options to choose from, but Shoreline Sightseeing came highly recommended to us, so that’s who we went with. The 75-minute tour will give you a unique view of the city and will educate you about its storied past (like the Great Chicago Fire and the original settlement location). Your guide will be funny and you’ll catch yourself pointing out architecture for the rest of your trip. Tours leave every 30 minutes, so don’t feel obligated to book in advance.


Millennium Park and Grant Park

Now that you’ve rested your bones for 75-minutes and the carb-coma has passed, it’s time to walk, so head towards Millennium Park. First, swing by The Bean (AKA Cloud Gate) and take all your required touristy pictures: your reflection in The Bean, standing in front of The Bean, the fun-house look inside The Bean…and so on and so forth. Unless you get there early in the morning, there’s going to be a crowd of people to compete with.


Next, swing by the Jay Pritzker Pavilion, and make sure to check the schedule to see if there are any fun events or free concerts happening during your time there. At this point, since you’re near the Lake Michigan side of the park, I usually walk on to Buckingham Fountain in Grant Park before completing the loop at Crown Fountain, which will leave you almost where you started. Crown Fountain is a must-visit for me, but it’s easy to miss with all the other attractions in Millennium Park to grab your attention. There are two massive 50-foot towers with LEDs showing a video of someone’s face. Pay attention because it is a video and the faces move, smile, wink, frown, etc. and you don’t want to miss what everyone else is giggling at. Each video lasts about 5 minutes  using various parts of 80-second videos. Some sections are in real-time, some are in slow-motion, but all are entrancing. Eventually, the mouth puckers for 15 seconds and then water squirts out for 30 seconds before the face changes to a different person and the 5 minutes starts over. Take off your shoes and wade around in the shallow reflection pool, or grab a space on one of the nearby walls. There are plenty of food vendors around too if you need a quick snack.IMG_8115

Chicago Theater and Garrett Popcorn

At this point, you’re probably ready for a quick break and air conditioning, so we went back to the hotel to decide where to eat and change clothes for the evening. But on the way back, we made a couple VERY important Chicago stops: Garrett Popcorn and the Chicago Theater. At Garrett, you have three classic choices: Buttery, CheeseCorn and CaramelCrisp. My recommendation is the Garrett Mix, which includes the CheeseCorn and CaramelCrisp – the perfect sweet and salty mixture. It doesn’t keep well unless you purchase a tin, so I’d recommend splitting a small or medium to tide you over until dinner. The Chicago Theater marquee is considered the, “unofficial emblem of the city” and has been an official Chicago landmark since 1983. Though it’s great to see at any time of day, I definitely recommend walking by at night to get the full effect.


Epic Burger

We wanted a quick (cheap) dinner with local ties, so Yelp pointed us to Epic Burger, a Chicago burger chain since 2008, with all but two locations in the heart of the city. Epic Burger offers non-processed, all-natural food at a reasonable price. We read their website, which said their food is prepared without drugs, artificial colors or flavors, nitrates, phosphates, preservative or various other additives found in our everyday food, so we were sold. Epic Burger did not disappoint. They offered a great selection of premium Wisconsin cheeses (Jason was a fan of the horseradish havarti and I thoroughly enjoyed the blue cheese) and had sweet potato waffle fries with a special sauce that paired perfectly. Here’s hoping Epic Burger catches on, and moves south. Note: Epic Burger does not accept cash – card only (remember, I AM a banker first, so I found this very interesting).


Navy Pier

Now it’s time to head to the Navy Pier. Check the firework schedule, because if you’re there when that’s happening, you’ll want to make sure you are at the Pier at night. We had other plans, so we went to the Pier around dusk to catch the first glimpse of the pier attractions and Chicago skyline lit up. As you can see from the picture below, rain was upon us, so stay aware of the quick-changing weather off Lake Michigan.


Evening Activities – Hamilton

There are plenty of evening activities to do in Chicago – the above mentioned fireworks, lake tour to see the skyline from afar, one of the observation decks, etc. – but we decided to go to our first Broadway in Chicago show. Since it opened in New York City, Hamilton has been the biggest show success in years. A mostly rap-opera musical (with some parts sung) turned Broadway on its head and plays to sold out crowds every night. Hamilton opened in Chicago in 2016, a year after opening in New York City. Tickets are expensive, but if you’re patient it can pay off. We started looking on Ticketmaster about an hour and a half before the 8pm show. Unfortunately, Ticketmaster’s iPhone app disallows you from looking at shows 90 minutes beforehand, so the trick is to delete the app off your phone and use Safari (if you don’t delete the app, Safari will continue to open it, causing problems). About an hour before the show, a pair of “Limited View Seating” seats in the orchestra became available, so we jumped on them. Obviously if you’re there during the week, you’re more likely to not have to mortgage your house for tickets, but we were happy with our Saturday-evening purchase. We made our way to PrivateBank Theater and to our “Limited View Seating” seats, which meant we couldn’t see the second level of the stage. There were only a couple times performers were on the second level, and they didn’t stay there for long, so the seats were great. Obviously Hamilton was phenomenal. The show ended at 11pm (12am our bodies’ time), so we headed back to the hotel for a good nights rest.


Willis (Sears) Tower – The Skydeck

Since we were driving back to Kentucky on Sunday, we decided to stop by Willis Tower (formerly Sears Tower) first thing in the morning. As our guide said on the architectural tour, “W-I-L-L-I-S Tower, pronounced ‘Sears Tower'” – you’ll find few locals embracing the Willis name. I HIGHLY recommend you visit Willis Tower as soon as it opens, which is 9am March-September and 10am October-February. Purchase your tickets ahead of time online. If you get there a little before 9am, it should take you less than 30 minutes (even less during a weekday) to get to the top, so I would save your money and not purchase a fastpass. Once you’re at the Skydeck, keep making lefts all around the observatory until you find The Ledge – four retractable glass balconies, 1,353 feet above the ground, two of which are setup for professional photography. It’s VERY difficult to get a “good picture” of yourself on The Ledge for various reasons – lighting and crowd just to name a few. So take advantage of the professional photographers and pay the $30 for a 5×7 and two 4×6 pictures (or you can pay the $30 online at a later date for just the digital copy). After you’ve taken your pictures, wander back around and check out the various views. This is my favorite observatory in the United States, and I’ve been to most of the well-known ones (One World Trade Center, 30 Rock, Space Needle, Stratosphere, Tower of the Americas, etc). You’ll spend about 30 minutes at the top taking pictures and checking out the views.


Chicago is a great weekend trip. Did we see everything? Not even close. But we saw many of the main attractions of the city and have plenty more to check out on our next trip. I’ve been to Chicago a couple times and would recommend a Wrigley Field Tour as well, but it will take up quite a bit of time, so if you’re cramming in as much as possible, I’d save that for another trip.

One thought on “Chicago In a Weekend

Add yours

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Blog at

Up ↑

%d bloggers like this: